Substituted tryptamine

Short description: Class of indoles

The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN1=RN2=Rα = H. The structure of substituted tryptamines with all positions labeled.

Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring system, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids are found in fungi, plants and animals; and sometimes used by humans for the neurological or psychotropic effects of the substance. Prominent examples of tryptamine alkaloids include psilocybin (from "psilocybin mushrooms") and DMT. In South America, dimethyltryptamine is obtained from numerous plant sources, like chacruna, and it is often used in ayahuasca brews. Many synthetic tryptamines have also been made, including the migraine drug sumatriptan, and psychedelic drugs. A 2022 study has found the variety of tryptamines present in wild mushrooms may affect the therapeutic impact.[1]

The tryptamine structure, in particular its indole ring, may be part of the structure of some more complex compounds, for example cyclized tryptamines like LSD, ibogaine, harmaline, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Alexander Shulgin and Ann Shulgin in 1997 under the title TiHKAL (Tryptamines I Have Known and Loved).[2]

## Contents

* 1 Use and effects
* 1.1 Ring-unsubstituted tryptamines
* 1.2 4-Hydroxytryptamines
* 1.3 5-Hydroxytryptamines
* 1.4 5-Methoxytryptamines
* 1.5 α-Alkyltryptamines
* 1.6 Other tryptamines
* 2 Interactions
* 3 Pharmacology
* 3.1 Pharmacodynamics
* 4 Chemistry
* 4.1 Synthesis
* 5 List of substituted tryptamines
* 5.1 List of substituted α-alkyltryptamines
* 5.2 List of substituted β-ketotryptamines
* 5.3 Cyclized tryptamines
* 6 Related compounds
* 7 Overview table
* 8 See also
* 9 References
* 10 External links

## Use and effects

The doses, potencies, durations, and effects of psychedelic tryptamines have been reviewed by Alexander Shulgin and other authors.[3][4][5][6][2][7][8][9][10][11]

### Ring-unsubstituted tryptamines

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Oral doses and durations of ring-unsubstituted tryptamines Compound | Chemical name | Dose | Duration

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Tryptamine (T) | Tryptamine | >100 mga | –
NMT | N-Methyltryptamine | Unknownb | –
NET | N-Ethyltryptamine | Unknown | Unknown
NPT | N-Propyltryptamine | Unknown | Unknown
NiPT | N-Isopropyltryptamine | Unknown | Unknown
NsBT | N-sec-Butyltryptamine | 25–75 mg | "Short"
NtBT | N-tert-Butyltryptamine | 5–20 mg | Unknown
NAT | N-Amyltryptamine | >100 mg | –
NHT | N-Hexyltryptamine | >100 mg | –
DMT | N,N-Dimethyltryptamine | >350–1,000 mgc | –
DET | N,N-Diethyltryptamine | 50–150 mg | 2–4 hours
DPT | N,N-Dipropyltryptamine | 100–250 mg | 2–4 hours
DiPT | N,N-Diisopropyltryptamine | 25–100 mg (15–150 mg+) | 4–8 hours
DALT | N,N-Diallyltryptamine | 60–80 mg | <3 hours
DBT | N,N-Dibutyltryptamine | ≥100 mg | Unknown
DAT | N,N-Diamyltryptamine | Unknown | Unknown
DHT | N,N-Dihexyltryptamine | >100 mg | –
MET | N-Methyl-N-ethyltryptamine | 80–100 mg | Unknown
MPT | N-Methyl-N-propyltryptamine | >50 mg | Unknown
MiPT | N-Methyl-N-isopropyltryptamine | 10–25 mg | 3–4 hours
MALT | N-Methyl-N-allyltryptamine | 25–50 mg | Unknown
MBT | N-Methyl-N-butyltryptamine | 250–400 mg | 4–6 hours
MsBT | N-Methyl-N-sec-butyltryptamine | 250–400 mg | Unknown
EPT | N-Ethyl-N-propyltryptamine | Unknown | Unknown
EiPT | N-Ethyl-N-isopropyltryptamine | 24–40 mg | 4–6 hours
PiPT | N-Propyl-N-isopropyltryptamine | Unknown | Unknown
Pyr-T | N,N-Tetramethylenetryptamine | Unknown | Unknown
Pip-T | N,N-Pentamethylenetryptamine | Unknown | Unknown
Mor-T | 3-(2-Morpholinoethyl)indole | Unknownd | Unknown

### 4-Hydroxytryptamines

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Oral doses and durations of 4-hydroxytryptamines Compound | Chemical name | Dose | Duration

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4-HT (4-HO-T) | 4-Hydroxytryptamine | Unknown | Unknown
Norbaeocystin (4-PO-T) | 4-Phosphoryloxytryptamine | Unknown | Unknown
Norpsilocin (4-HO-NMT) | 4-Hydroxy-N-methyltryptamine | Unknown | Unknown
Baeocystin (4-PO-NMT) | 4-Phosphoryloxy-N-methyltryptamine | 4–10 mga | Unknown
Psilocin (4-HO-DMT) | 4-Hydroxy-N,N-dimethyltryptamine | 10–20 mg (5–40 mg+) | 3–6 hours
Psilocybin (4-PO-DMT) | 4-Phosphoryloxy-N,N-dimethyltryptamine | 10–20 mg (5–40 mg+) | 3–6 hours
4-AcO-DMT (psilacetin) | 4-Acetoxy-N,N-dimethyltryptamine | 10–30 mg | 3–8 hours
4-PrO-DMT | 4-Propionyloxy-N,N-dimethyltryptamine | Unknown | Unknown
4-HO-DET (ethocin) | 4-Hydroxy-N,N-diethyltryptamine | 10–25 mg | 4–6 hours
Ethocybin (4-PO-DET) | 4-Phosphoryloxy-N,N-diethyltryptamine | 15–30 mg | 4–6 hours
4-HO-DPT (deprocin) | 4-Hydroxy-N,N-dipropyltryptamine | >20 mg | 5–8 hours
4-HO-DiPT (iprocin) | 4-Hydroxy-N,N-diisopropyltryptamine | 12–20 mg (3–30 mg+) | 2–3 hours
4-AcO-DiPT (ipracetin) | 4-Acetoxy-N,N-diisopropyltryptamine | 6–10 mg | Unknown
Luvesilocin (4-GO-DiPT) | 4-Glutaryloxy-N,N-diisopropyltryptamine | Unknownb | Unknownb
4-HO-DALT (daltocin) | 4-Hydroxy-N,N-diallyltryptamine | Unknown | Unknown
4-HO-DBT | 4-Hydroxy-N,N-dibutyltryptamine | >20 mg | Unknown
4-HO-DiBT | 4-Hydroxy-N,N-diisobutyltryptamine | >20 mg | Unknown
4-HO-DtBT | 4-HydroxyN,N-di-tert-butyltryptamine | Unknown | Unknown
4-HO-MET (metocin) | 4-Hydroxy-N-methyl-N-ethyltryptamine | 10–20 mg (2–45 mg+) | 4–6 hours
4-HO-MPT (meprocin) | 4-Hydroxy-N-methyl-N-propyltryptamine | 8–30 mg | Unknown
4-HO-MiPT (miprocin) | 4-Hydroxy-N-methyl-N-isopropyltryptamine | 12–25 mg (6–30 mg) | 4–6 hours
4-HO-MALT (maltocin) | 4-Hydorxy-N-methyl-N-allyltryptamine | Unknown | Unknown
4-HO-MtBT | 4-Hydroxy-N-methyl-N-tert-butyltryptamine | >15 mg | Unknown
4-HO-EPT (eprocin) | 4-Hydroxy-N-ethyl-N-propyltryptamine | Unknown | Unknown
4-HO-EiPT | 4-Hydroxy-N-ethyl-N-isopropyltryptamine | Unknown | Unknown
4-HO-PiPT (piprocin) | 4-Hydroxy-N-propyl-N-isopropyltryptamine | Unknown | Unknown
4-HO-TMT | 4-Hydroxy-N,N,N-trimethyltryptamine | Unknown | Unknown
Aeruginascin (4-PO-TMT) | 4-Phosphoryloxy-N,N,N-trimethyltryptamine | Unknown | Unknown
4-HO-pyr-T | 4-Hydroxy-N,N-tetramethylenetryptamine | >20 mg | Unknown
Footnotes: a = Baeocystin has conflicting reports, some say that it's active and some say that it's inactive. b = Luvesilocin is known to be active subcutaneously at doses of 5 to 40 mg with an average duration of 3.6 hours. Refs: [3][4][2][7][8][9][11][10] Individual: [12][13][14][15][16]

### 5-Hydroxytryptamines

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Oral doses and durations of 5-hydroxytryptamines Compound | Chemical name | Dose | Duration

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Serotonin (5-HT, 5-HO-T) | 5-Hydroxytryptamine | >100 mga | –
N-Methylserotonin (norbufotenin; 5-HO-NMT) | 5-Hydroxy-N-methyltryptamine | Unknown | Unknown
Bufotenin (5-HO-DMT) | 5-Hydroxy-N,N-dimethyltryptamine | >100 mgb | –
O-Acetylbufotenin (5-AcO-DMT) | 5-Acetoxy-N,N-dimethyltryptamine | Unknown | Unknown
O-Pivalylbufotenin (5-t-BuCO-DMT) | 5-Pivaloxy-N,N-dimethyltryptamine | Unknown | Unknown
5-HO-DET | 5-Hydroxy-N,N-diethyltryptamine | Unknown | Unknown
5-HO-DPT (DiPS, NDPS) | 5-Hydroxy-N,N-dipropyltryptamine | Unknown | Unknown
5-HO-DiPT | 5-Hydroxy-N,N-diisopropyltryptamine | Unknown | Unknown
5-HO-MET | 5-Hydroxy-N-methyl-N-ethyltryptamine | Unknown | Unknown
Footnotes: a = Serotonin does not cross the blood–brain barrier and is not psychoactive. b = Bufotenin is not orally active, but is active intravenously at doses of 8 to 16 mg with a duration of 1 to 2 hours and is active via insufflation and other parenteral routes. Refs: [3][4][2][11] Individual: [17][18][19][20]

### 5-Methoxytryptamines

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Oral doses and durations of 5-methoxytryptamines Compound | Chemical name | Dose | Duration

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5-MT (5-MeO-T) | 5-Methoxytryptamine | Unknown | Unknown
5-MeO-NMT | 5-Methoxy-N-methyltryptamine | Unknown | Unknown
5-MeO-NET | 5-Methoxy-N-ethyltryptamine | Unknown | Unknown
5-MeO-NiPT | 5-Methoxy-N-isopropyltryptamine | Unknown | Unknown
5-MeO-DMT (mebufotenin) | 5-Methoxy-N,N-dimethyltryptamine | >35 mga | –
5-MeO-DET | 5-Methoxy-N,N-diethyltryptamine | 1–3 mg | 3–4 hours
5-MeO-DPT | 5-Methoxy-N,N-dipropyltryptamine | 6–10 mg | 2–4 hours
5-MeO-DiPT | 5-Methoxy-N,N-diisopropyltryptamine | 6–12 mg | 4–8 hours
5-MeO-DALT | 5-Methoxy-N,N-diallyltryptamine | 12–25 mg | 2–4 hours
5-MeO-DBT | 5-Methoxy-N,N-dibutyltryptamine | Unknown | Unknown
5-MeO-DsBT | 5-Methoxy-N,N-di-sec-butyltryptamine | Unknown | Unknown
5-MeO-MET | 5-Methoxy-N-methyl-N-ethyltryptamine | Unknown | Unknown
5-MeO-MPT | 5-Methoxy-N-methyl-N-propyltryptamine | Unknown | Unknown
5-MeO-MiPT | 5-Methoxy-N-methyl-N-isopropyltryptamine | 4–6 mg (0.5–20 mg+) | 4–6 hours
5-MeO-MALT | 5-Methoxy-N-methyl-N-allyltryptamine | Unknown | Unknown
5-MeO-MsBT | 5-Methoxy-N-methyl-N-sec-butyltryptamine | 10–30 mg | 3–4 hours
5-MeO-EPT | 5-Methoxy-N-ethyl-N-propyltryptamine | Unknown | Unknown
5-MeO-EiPT | 5-Methoxy-N-ethyl-N-isopropyltryptamine | Unknown | Unknown
5-MeO-PiPT | 5-Methoxy-N-propyl-N-isopropyltryptamine | Unknown | Unknown
5-MeO-iPALT (ASR-3001) | 5-Methoxy-N-isopropyl-N-allyltryptamine | 8–14 mg | 1.5–2.5 hours
5-MeO-pyr-T | 5-Methoxy-N,N-tetramethylenetryptamine | 0.5–2 mg | Several hours
Melatonin (5-MeO-NAcT) | 5-Methoxy-N-acetyltryptamine | 1–10 mgb | A few hours
Footnotes: a = 5-MeO-DMT is not orally active, but is active at a dose of 2 to 20 mg smoked or 2 to 3 mg intravenously, with a duration of 5 to 20 minutes. Also orally active with an MAOI at doses of 10 to 25 mg. b = Melatonin is not a psychedelic but a hypnotic and is non-hallucinogenic at doses of up to 1,200 mg. Refs: [3][4][2][7][8][9][11] Individual: [13][21][22]

### α-Alkyltryptamines

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Oral doses and durations of α-alkyltryptamines Compound | Chemical name | Dose | Duration

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AMT (α-methyl-T; Indopan)a | α-Methyltryptamine | 15–40 mg | 12–16 hours
AET (α-ethyl-T; etryptamine; Monase)b | α-Ethyltryptamine | 100–160 mg | 6–8 hours
α,N-DMT (N-methyl-AMT)c | α-Methyl-N-methyltryptamine | 50–100 mg | 6–8 hours
α,N,N-TMT (N,N-dimethyl-AMT) | α,N,N-Trimethyltryptamine | Unknownd | Unknown
2,α-DMT (2-methyl-AMT) | 2-Methyl-α-methyltryptamine | 300–500 mg | 7–10 hours
4-HO-AMT (MP-14) | 4-Hydroxy-α-methyltryptamine | 15–20 mg+ | Unknown
4-Methyl-AMT (MP-809) | 4-Methyl-α-methyltryptamine | 20–60 mg+ | Unknown
5-Fluoro-AMT (PAL-212, PAL-544) | 5-Fluoro-α-methyltryptamine | 25 mg+ | >9 hours
5-Chloro-AMT (PAL-542) | 5-Chloro-α-methyltryptamine | Unknown | Unknown
5-Fluoro-AET (PAL-545) | 5-Fluoro-α-ethyltryptamine | Unknown | Unknown
5-Chloro-AET (PAL-526) | 5-Chloro-α-ethyltryptamine | Unknown | Unknown
6-Fluoro-AMT | 6-Fluoro-α-methyltryptamine | 25–75 mg | "Long"
α-Methylserotonin (AMS; 5-HO-AMT) | α-Methyl-5-hydroxytryptamine | Unknown | Unknown
α,O-DMS (5-MeO-AMT) | α-Methyl-5-methoxytryptamine | 2.5–5 mg (0.5–15 mg) | 12–18 hours
α,N,O-TMS (5-MeO-N-methyl-AMT) | α-Methyl-5-methoxy-N-methyltryptamine | 10–20 mg | 6–8 hours
α,N,N,O-TeMS (5-MeO-N,N-dimethyl-AMT) | 5-Methoxy-α,N,N-trimethyltryptamine | Unknown | Unknown
5-MeO-AET | α-Ethyl-5-methoxytryptamine | ~70 mg | Several hours
Bk-NM-AMT (β-keto-N-methyl-AMT)e | α-Methyl-β-keto-N-methyltryptamine | Unknown | Unknown
Footnotes: a = AMT is a not only a psychedelic but is also a stimulant and entactogen. b = AET is an entactogen and stimulant and is not a psychedelic. c = α,N-DMT is a stimulant and is not a psychedelic or entactogen. d = α,N,N-TMT has been reported to be an active psychedelic orally but to be much less potent than AMT. e = Bk-NM-AMT is expected to be an entactogen and stimulant but not a psychedelic. Refs: [3][4][2][7][8][11] Individual: [23][24]

### Other tryptamines

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Oral doses and durations of other tryptamines Compound | Chemical name | Dose | Duration

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Lespedamine (1-MeO-DMT) | 1-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown
2-Methyl-DMT | 2-Methyl-N,N-dimethyltryptamine | 50–100 mg | 4–6 hours
2-Methyl-DET | 2-Methyl-N,N-diethyltryptamine | 80–120 mg | 6–8 hours
4-MeO-DMT | 4-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown
4-MeO-DET | 4-Methoxy-N,N-diethyltryptamine | >30 mg | Unknown
4-MeO-DiPT | 4-Methoxy-N,N-diisopropyltryptamine | Unknown | Unknown
4-MeO-MiPT | 4-Methoxy-N-methyl-N-isopropyltryptamines | 20–30 mg | 4–6 hours
4,5-MDO-DMT | 4,5-Methylenedioxy-N,N-dimethyltryptamine | Unknown | Unknown
4,5-MDO-DiPT | 4,5-Methylenedioxy-N,N-diisopropyltryptamine | >25 mg | Unknown
5-Fluoro-DMT | 5-Fluoro-N,N-dimethyltryptamine | Unknown | Unknown
5-Chloro-DMT | 5-Chloro-N,N-dimethyltryptamine | Unknown | Unknown
5-Bromo-DMT | 5-Bromo-N,N-dimethyltryptamine | Unknowna | Unknown
Bretisilocin (5-fluoro-MET) | 5-Fluoro-N-methyl-N-ethyltryptamine | Unknownb | Unknownb
5-MeO-2-TMT | 5-Methoxy-2-methyl-N,N-dimethyltryptamine | 75–150 mg | 5–10 hours
5-MeS-DMT | 5-Methylthio-N,N-dimethyltryptamine | Unknownc | Unknownc
5,6-MeO-MiPT | 5,6-Dimethoxy-N-methyl-N-isopropyltryptamine | >75 mg | Unknown
5,6-MDO-DMT | 5,6-Methylenedioxy-N,N-dimethyltryptamine | >5 mg | Unknown
5,6-MDO-DiPT | 5,6-Methylenedioxy-N,N-diisopropyltryptamine | Unknown | Unknown
5,6-MDO-MiPT | 5,6-Methylenedioxy-N-methyl-N-isopropyltryptamine | >50–60 mg | Unknown
6-Fluoro-DMT | 6-Fluoro-N,N-dimethyltryptamine | Unknown | Unknown
6-Fluoro-DET | 6-Fluoro-N,N-diethyltryptamine | >80 mg | Unknown
6-HO-DMT | 6-Hydroxy-N,N-dimethyltryptamine | >80 mg | Unknown
6-HO-DET | 6-Hydroxy-N,N-diethyltryptamine | ≥10 mgd | 3–4 hoursd
6-MeO-DMT | 6-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown
6-MeO-DiPT | 6-Methoxy-N,N-diisopropyltryptamine | >50 mg | Unknown
6-MeO-MiPT | 6-Methoxy-N-methyl-N-isopropyltryptamine | >50 mg | Unknown
7-HO-DMT | 7-Hydroxy-N,N-dimethyltryptamine | Unknown | Unknown
7-MeO-DMT | 7-Methoxy-N,N-dimethyltryptamine | Unknown | Unknown
7-MeO-DiPT | 7-Methoxy-N,N-diisopropyltryptamine | >70 mg | Unknown
7-MeO-MiPT | 7-Methoxy-N-methyl-N-isopropyltryptamine | >70 mg | Unknown
Footnotes: a = 5-Bromo-DMT is active via smoking at a dose of 20 to 50 mg. b = Bretisilocin is active intravenously with a dose range of 10 to 20 mg and a duration of 60 to 90 minutes. c = 5-MeS-DMT's oral dose and duration are unknown, but smoked the dose is 15 to 30 mg and the duration is 10 to 30 minutes or <1 hour. d = Controversial and uncertain. Refs: [3][4][2][9][11] Individual: [25][26][27]

## Interactions

## Pharmacology

### Pharmacodynamics

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Serotonin receptor affinities (Ki, nM) of selected psychedelic tryptamines (Jain et al., 2025)[28] Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 | SERT

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DMT | 269 | 447 | 117 | 380 | 380 | 112 | 257 | – | 2,090 | 275 | 69 | 2,400
Psilocin | 372 | 191 | 98 | 339 | 200 | 25 | 245 | – | 447 | 79 | 87 | 2,570
Psilocybin | 5,250 | – | 195 | – | 851 | 479 | 3,090 | – | – | 776 | – | –
4-AcO-MALT | 977 | – | 871 | 417 | 692 | 25 | 631 | – | – | 661 | 794 | 3,090
Bufotenin | 8.3 | 59 | 22 | 25 | 224 | 6.2 | 209 | 166 | 302 | 18 | 8.9 | 1,120
5-MeO-DMT | 10 | 91 | 21 | 575 | 200 | 15 | 490 | – | 589 | 25 | 4.4 | –
5-MeO-DiPT | 170 | – | 871 | – | 324 | 46 | – | – | – | 2,190 | – | –
5-MeO-DALT | 17 | 1,020 | 54 | 977 | 457 | 100 | 2,240 | – | – | 162 | 60 | 4,470
5-MeO-EiPT | 54 | 1,170 | 174 | – | 1,622 | 98 | – | – | – | 407 | 661 | 5,620
LSD | 5.9 | 21 | 3.5 | 135 | 8.5 | 5.5 | 17 | – | 1.8 | 16 | 8.5 | –

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Serotonin receptor affinities (Ki, nM) of selected psychedelic tryptamines (Ray, 2010)[29] Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 | SERT

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DMT | >10,000 | >10,000 | 93 | 456 | 2,323 | 108 | 335 | >10,000 | 611 | 487 | 883 | 3,742
DPT | 32 | 854 | 619 | 2,338 | 2,579 | 42 | 1,567 | >10,000 | 4,373 | 4,543 | 284 | 157
DiPT | 121 | >10,000 | 3,742 | >10,000 | >10,000 | 399 | >10,000 | >10,000 | >10,000 | >10,000 | 3,423 | 1,258
Psilocin | 63 | 305 | 19 | 44 | 340 | 4.7 | 141 | >10,000 | 70 | 72 | 72 | 852
5-MeO-DMT | 1.9 | 74 | 6.3 | 360 | 2,011 | 3,884 | 538 | >10,000 | 277 | 36 | 3.9 | 2,032
5-MeO-DiPT | 132 | 5,137 | 1,718 | >10,000 | >10,000 | 163 | >10,000 | >10,000 | >10,000 | >10,000 | 1,231 | 2,531
5-MeO-MiPT | 12 | 303 | 23 | 3,496 | 448 | 59 | 2,186 | >10,000 | 953 | 130 | 20 | 6,409
6-Fluoro-DMT | 393 | 218 | 55 | 461 | 866 | 30 | 674 | >10,000 | 961 | 26 | 41 | 145
5-MeO-2-TMT | 200 | >10,000 | 250 | 1,800 | >10,000 | ? | 4,020 | ? | 10,450 | 60 | 145 | >10,000
EMDT | 170 | >10,000 | 290 | 520 | >10,000 | ? | 1,810 | ? | 4,620 | 16 | 300 | >10,000
Ibogaine | >10,000 | >10,000 | >10,000 | ? | 14,142 | ? | >10,000 | >10,000 | ? | ? | ? | 549
LSD | 7.3 | 3.9 | 7.8 | 93 | 11 | 30 | 31 | >10,000 | 9 | 6.9 | 6.6 | >10,000

## Chemistry

### Synthesis

The chemical syntheses of numerous tryptamines have been described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved).[2] A well-known and widely used synthetic approach for making tryptamines is the Speeter–Anthony route, which starts with indole.[30][31][32] Other tryptamine synthesis routes have also been described, for instance starting with tryptamine rather than indole.[30][31] The chemical syntheses of the psychedelic tryptamines bufotenin (5-HO-DMT) and 5-MeO-DMT (mebufotenin) have been comprehensively reviewed.[33]

## List of substituted tryptamines

This list is incomplete; you can help by expanding it.

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Structure  | Name  | Origin  | Ring sub.  | RN1 | RN2 | Chemical name  | CAS #

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| Tryptamine (T) | Animals, plants, fungi | H | H | H | 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine | 61-54-1
| N-Methyltryptamine (NMT) | Plants | H | H | CH3 | N-methyltryptamine | 61-49-4
| 2-HO-NMT | Plants | 2-OH | H | CH3 | 2-hydroxy-N-methyltryptamine | 106987-89-7
| 5-MeO-NMT | Plants | 5-OCH3 | H | CH3 | 5-methoxy-N-methyltryptamine | 2009-03-2
| Serotonin (5-HT) | Animals, plants | 5-OH | H | H | 5-hydroxytryptamine | 50-67-9
| N-Methylserotonin (NMS; norbufotenin; 5-HO-NMT) | Plants | 5-OH | H | CH3 | 5-hydroxy-N-methyltryptamine | 1134-01-6
| Bufotenin (5-HO-DMT) | Animals, plants, fungi | 5-OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyltryptamine | 487-93-4
| Bufotenidine (5-HTQ) | Amphibians | 5-O− | (CH3)3 | 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate | 487-91-2
| Bufoviridine (5-SO-DMT) | Amphibians | 5-SO | CH3 | CH3 | 5-sulfooxy-N,N-dimethyltryptamine | 16369-08-7
| 5-Methoxytryptamine (5-MT; 5-MeO-T) | Animals, plants | 5-OCH3 | H | H | 5-methoxytryptamine | 608-07-1
| Melatonin (5-MeO-NAcT) | Animals, plants, microbes | 5-OCH3 | H | O=C-CH3 | 5-methoxy-N-acetyltryptamine | 73-31-4
| N-Acetylserotonin (NAS; normelatonin; 5-HO-NAcT) | Animals | 5-OH | H | O=C-CH3 | 5-hydroxy-N-acetyltryptamine | 1210-83-9
| 6-Hydroxymelatonin | Animals | 5-OCH3, 6-OH | H | O=C-CH3 | N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide | 2208-41-5
Error creating thumbnail:  | 4-Hydroxytryptamine (4-HT) | Fungi | 4-OH | H | H | 4-hydroxytryptamine | 570-14-9
| 4-HO-NMT | Fungi | 4-OH | H | CH3 | 4-hydroxy-N-methyltryptamine | 28363-70-4
| Psilocin (4-HO-DMT) | Fungi | 4-OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyltryptamine | 520-53-6
File:4-HO-TMT.svg | 4-HO-TMT | Fungi | 4-OH | CH3 | CH3 | 4-hydroxy-N,N,N-trimethyltryptammonium | 262285-41-6
| Norbaeocystin (4-PO-T) | Fungi | 4-OPO3H2 | H | H | 4-phosphoryloxy-tryptamine | 21420-59-7
File:Baeocystin v2.svg | Baeocystin (4-PO-NMT) | Fungi | 4-OPO3H2 | H | CH3 | 4-phosphoryloxy-N-methyl-tryptamine | 21420-58-6
| Psilocybin (4-PO-DMT) | Fungi | 4-OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyltryptamine | 520-52-5
| Aeruginascin (4-PO-TMT) | Fungi | 4-OPO3H2 | (CH3)3 | [3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate | 114264-95-8
| Dimethyltryptamine (DMT) | Animals, plants | H | CH3 | CH3 | N,N-dimethyltryptamine | 61-50-7
| Lespedamine (1-MeO-DMT) | Plants | 1-OCH3 | CH3 | CH3 | 1-methoxy-N,N-dimethyltryptamine | 4335-93-7
| 5-MeO-DMT (mebufotenin) | Animals, plants | 5-OCH3 | CH3 | CH3 | 5-methoxy-N,N-dimethyltryptamine | 1019-45-0
| 5-Bromo-DMT | Marine sponges, invertebrates | 5-Br | CH3 | CH3 | 5-bromo-N,N-dimethyltryptamine | 17274-65-6
| 6-Bromotryptamine | Marine invertebrates | 6-Br | H | H | 6-bromotryptamine | 96624-18-9
| 5,6-Dibromotryptamine | Marine invertebrates | 5,6-Br | H | H | 5,6-dibromotryptamine |
| 5,6-Dibromo-NMT | Marine invertebrates | 5,6-Br | H | CH3 | 5,6-dibromo-N-methyltryptamine |
| 5,6-Dibromo-DMT | Marine sponges, invertebrates | 5,6-Br | CH3 | CH3 | 5,6-dibromo-N,N-dimethyltryptamine | 72853-80-6
| Desformylflustrabromine (dFBr) | Marine invertebrates | 2-(α,α-dimethylallyl), 6-Br | H | CH3 | 2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine | 474657-72-2
| Convolutindole A | Marine invertebrates | 2,4,6-Br, 1,7-OCH3 | CH3 | CH3 | 1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine | 443356-86-3
File:Α,α-Dideuterotryptamine.svg | α,α-Dideuterotryptamine[34] | artificial | H | H | H | α,α-Dideuterotryptamine | ?
File:Β,β-Dideuterotryptamine.svg | β,β-Dideuterotryptamine[35] | artificial | H | H | H | β,β-Dideuterotryptamine | ?
File:1-Methyltryptamine.svg | 1-Methyltryptamine (1-MT)  | artificial  | 1-CH3 | H  | H  | 1-Methyltryptamine  | 7518-21-0
File:4-Methoxytryptamine structure.svg | 4-Methoxytryptamine (4-MeO-T)  | artificial  | 4-OCH3 | H  | H  | 4-Methoxytryptamine  | 3610-35-3
File:4-Fluorotryptamine structure.svg | 4-Fluorotryptamine (4-FT)  | artificial  | 4-F  | H  | H  | 4-Fluorotryptamine  | 467452-26-2
File:5-Methoxytryptamine-α,α,β,β-d4.svg | 5-Methoxytryptamine-α,α,β,β-d4 (5-MT-d4)[36] | artificial  | 5-OCH3 | H  | H  | α,α,β,β-Tetradeutero-5-methoxytryptamine  | 96236-05-4
File:5-Methyltryptamine.svg | 5-Methyltryptamine (5-MT)  | artificial  | 5-CH3 | H  | H  | 5-Methyltryptamine  | 1821-47-2
File:5-Fluorotryptamine structure.svg | 5-Fluorotryptamine (5-FT)  | artificial  | 5-F  | H  | H  | 5-Fluorotryptamine  | 576-16-9
File:5-Chlorotryptamine.svg | 5-Chlorotryptamine (5-Cl-T)  | artificial  | 5-Cl  | H  | H  | 5-Chlorotryptamine  | 3764-94-1
File:5-Bromotryptamine.svg | 5-Bromotryptamine (5-Br-T)  | artificial  | 5-Br  | H  | H  | 5-Bromotryptamine  | 3610-42-2
File:6-Methyltryptamine.svg | 6-Methyltryptamine (6-MT)  | artificial  | 6-CH3 | H  | H  | 6-Methyltryptamine  | 62500-90-7
File:6-Hydroxytryptamine structure.svg | 6-Hydroxytryptamine (6-HT)  | artificial  | 6-OH  | H  | H  | 6-Hydroxytryptamine  | 443-31-2
File:6-Methoxytryptamine structure.svg | 6-Methoxytryptamine (6-MeO-T)  | artificial  | 6-OCH3 | H  | H  | 6-Methoxytryptamine  | 3610-36-4
File:6-Fluorotryptamine structure.svg | 6-Fluorotryptamine (6-FT)  | artificial  | 6-F  | H  | H  | 6-Fluorotryptamine  | 575-85-9
File:7-Methyltryptamine.svg | 7-Methyltryptamine (7-MT)  | artificial  | 7-CH3 | H  | H  | 7-Methyltryptamine  | 14490-05-2
File:7-Hydroxytryptamine.svg | 7-Hydroxytryptamine (7-HT)  | artificial  | 7-OH  | H  | H  | 7-Hydroxytryptamine  | 15700-23-9
File:7-Methoxytryptamine.svg | 7-Methoxytryptamine (7-MeO-T)  | artificial  | 7-OCH3 | H  | H  | 7-Methoxytryptamine  | 2436-04-6
File:7-Fluorotryptamine.svg | 7-Fluorotryptamine (7-F-T)  | artificial  | 7-F  | H  | H  | 7-Fluorotryptamine  | 191927-74-9
File:7-Chlorotryptamine structure.svg | 7-Chlorotryptamine (7-Cl-T)  | artificial  | 7-Cl  | H  | H  | 7-Chlorotryptamine  | 3804-16-8
| Acetryptine (5-acetyltryptamine; 5-AT)  | artificial  | 5-COCH3 | H  | H  | 5-Acetyltryptamine  | 3551-18-6
File:5-Phenoxytryptamine.svg | 5-Phenoxytryptamine (5-PhO-T)  | artificial  | 5-OC6H5 | H  | H  | 5-Phenoxytryptamine  | 31363-70-9
File:5-Benzyloxytryptamine chemical structure.svg | 5-Benzyloxytryptamine (5-BT)  | artificial  | 5-OCH2C6H5 | H  | H  | 5-Benzyloxytryptamine  | 20776-45-8
| 5-Carboxamidotryptamine (5-CT)  | artificial  | 5-CONH2 | H  | H  | 5-Carboxamidotryptamine  | 74885-09-9
File:5-Nitrotryptamine.svg | 5-Nitrotryptamine (Nitro-I)  | artificial  | 5-NO2 | H  | H  | 5-Nitrotryptamine  | 55747-72-3
| 5-(Nonyloxy)tryptamine (5-NOT) | artificial | 5-O(CH2)8CH3 | H | H | 5-Nonyloxytryptamine | 157798-12-4
| 2-Methyl-5-hydroxytryptamine | artificial  | 2-CH3, 5-OH  | H  | H  | 3-(2-aminoethyl)-2-methyl-1H-indol-5-ol  | 78263-90-8
File:N-Ethyltryptamine structure.svg | N-Ethyltryptamine (NET)  | artificial  | H  | H  | CH2CH3 | N-ethyltryptamine  | 61-53-0
File:N-Propyltryptamine.svg | N-Propyltryptamine (NPT)  | artificial  | H  | H  | CH2CH2CH3 | N-propyltryptamine  |
File:NiPT 2D.svg | N-Isopropyltryptamine (NiPT)  | artificial  | H  | H  | CH(CH3)2 | N-isopropyltryptamine  | 14121-10-9
File:N-Cyclopropyltryptamine.svg | N-Cyclopropyltryptamine (NcPT)  | artificial  | H  | H  | C3H5 | N-cyclopropyltryptamine  |
File:NsBT 2D.svg | N-sec-Butyltryptamine (NsBT)  | artificial  | H  | H  | CH(CH3)CH2CH3 | N-sec-butyltryptamine  |
| N-tert-Butyltryptamine (NtBT)  | artificial  | H  | H  | C(CH3)3 | N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine  | 1344092-44-9
File:Amyltrytamine.svg | N-Amyltryptamine (NAT)  | artificial  | H  | H  | (CH2)4CH3 | N-[2-(1H-indol-3-yl)ethyl]pentan-1-amine  |
File:N-Hexyltryptamine.svg | N-Hexyltryptamine (NHT)  | artificial  | H  | H  | (CH2)5CH3 | N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine  |
File:N-(2-Cyanoethyl)tryptamine.svg | N-(2-Cyanoethyl)tryptamine (CE-T)  | artificial  | H  | H  | CH2CH2C≡N  | N-(2-Cyanoethyl)tryptamine  | 105115-85-3
File:Benzyltryptamine.svg | N-Benzyltryptamine (NBnT)  | artificial  | H  | H  | CH2C6H5 | N-benzyltryptamine  | 15741-79-4
File:CPI-CG-8.svg | CPI-CG-8 | artificial  | H  | H  | (2-Indolylethyl)  | N-Methyl-N-(2-indolylethyl)tryptamine  | ?
| T-NBOMe (NBOMeT)  | artificial  | H  | H  | CH2C6H4(o-OCH3)  | N-(2-methoxybenzyl)tryptamine  | 418781-81-4
| 4-HO-NET | artificial  | 4-OH  | CH2CH3 | H  | 4-hydroxy-N-ethyltryptamine  |
Error creating thumbnail:  | 4-HO-NPT | artificial  | 4-OH  | CH(CH3)2 | H  | 4-hydroxy-N-propyltryptamine  |
File:4-HO-NiPT.svg | 4-HO-NiPT | artificial  | 4-OH  | CH(CH3)2 | H  | 4-hydroxy-N-isopropyltryptamine  |
File:4-HO-NALT 2D.svg | 4-HO-NALT | artificial  | 4-OH  | H  | H2C=CH-CH2 | 4-hydroxy-N-allyltryptamine  |
File:4-HO-NBT chemical structure.svg | 4-HO-NBT (4-HO-NnBT)  | artificial  | 4-OH  | H  | (CH2)3CH3 | 4-hydroxy-N-n-butyltryptamine  |
File:4-HO-NiBT chemical structure.svg | 4-HO-NiBT  | artificial  | 4-OH  | H  | CH2CH(CH3)2 | 4-hydroxy-N-isobutyltryptamine  |
File:4-HO-NsBT chemical structure.svg | 4-HO-NsBT  | artificial  | 4-OH  | H  | CH(CH3)CH2CH3 | 4-hydroxy-N-sec-butyltryptamine  |
File:4-HO-NtBT chemical structure.svg | 4-HO-NtBT  | artificial  | 4-OH  | H  | C(CH3)3 | 4-hydroxy-N-tert-butyltryptamine  |
File:4-HO-NBnT 2D.svg | 4-HO-NBnT | artificial  | 4-OH  | H  | CH2C6H5 | 4-hydroxy-N-benzyltryptamine  |
| 1-Me-4-HO-T-NBOMe [37] | artificial  | 1,Me, 4-OH  | H  | CH2C6H4-o-OCH3 | 1-methyl-4-hydroxy-N-(2-methoxybenzyl)tryptamine  |
File:4-HO-NcHT chemical structure.svg | 4-HO-NcHT  | artificial  | 4-OH  | H  | C6H11 | 4-hydroxy-N-cyclohexyltryptamine  |
File:5-MeO-NET.svg | 5-MeO-NET | artificial  | 5-OCH3 | H  | CH2CH3 | 5-methoxy-N-ethyltryptamine  | 1019-46-1
File:5-MeO-NIPT.svg | 5-MeO-NiPT | artificial  | 5-OCH3 | H  | CH(CH3)2 | 5-methoxy-N-isopropyltryptamine  | 109921-55-3
File:5-MeO-NsBT.svg | 5-MeO-NsBT | artificial  | 5-OCH3 | H  | CH(CH3)CH2CH3 | 5-methoxy-N-sec-butyltryptamine  |
File:5-MeO-NBnT 2D.svg | 5-MeO-NBnT | artificial  | 5-OCH3 | H  | CH2C6H5 | 5-methoxy-N-benzyltryptamine  | 25100-31-6
File:5-MeO-T-NBOMe.svg | 5-MeO-T-NBOMe | artificial  | 5-OCH3 | H  | CH2C6H4(o-OCH3)  | 5-methoxy-N-(ortho-methoxybenzyl)tryptamine  | 1335331-37-7
File:5MT-NB3OMe.svg | 5-MeO-T-NB3OMe [38] | artificial  | 5-OCH3 | H  | CH2C6H4(m-OCH3)  | 5-methoxy-N-(meta-methoxybenzyl)tryptamine  | 1648553-42-7
| 5-MeO-NBpBrT | artificial  | 5-OCH3 | H  | CH2C6H4(p-Br)  | N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine  | 155639-13-7
| 5-MeO-34MPEMT [39] | artificial  | 5-OCH3 | CH3 | CH2CH2C6H3(p,m-OCH3)  | N-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]-2-(5-methoxy-1H-indol-3-yl)ethanamine  |
| Idalopirdine | artificial  | 6-F  | H  | CH2C6H4(m-OCH2CF2CF2H)  | 2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoro-propoxy)benzyl)ethanamine  | 467459-31-0
| Z2876442907[40] | artificial  | 4-CH3 | H  | CH2(C3HNS)-COOCH2CH3 | ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate  |
| Cis-2',5'-dimethyl-4-HO-azt-T [41] | artificial | 4-OH | cis-(CHCH3)CH2(CHCH3) | 3-{2-[(2R,4S)-2,4-dimethylazetidin-1-yl]ethyl}-1H-indol-4-ol |
File:Pyr-T.svg | Pyr-T | artificial | H | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole | 14008-96-9
File:4-HO-pyr-T.svg | 4-HO-pyr-T | artificial | 4-OH | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol | 63097-26-7
| Cis-2',5'-dimethyl-4-HO-pyr-T [41] | artificial | 4-OH | cis-(CHCH3)CH2CH2(CHCH3) | 3-{2-[(2R,5S)-2,5-dimethylpyrrolidin-1-yl]ethyl}-1H-indol-4-ol |
File:5-MeO-pyr-T.svg | 5-MeO-pyr-T | artificial | 5-OCH3 | (CH2)4 | 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole | 3949-14-2
File:4-F-5-MeO-pyr-T.svg | 4-F-5-MeO-pyr-T | artificial | 4-F-5-OCH3 | (CH2)4 | 4-Fluoro-5-methoxy-3-(2-pyrrolidin-1-ylethyl)-1H-indole | 344790-93-8
File:Pip-Tryptamine.svg | Pip-T | artificial | H | (CH2)5 | 3-(2-Piperidin-1-ylethyl)-1H-indole | 26628-87-5
File:5-MeO-pip-T.svg | 5-MeO-pip-T | artificial | 5-OCH3 | (CH2)5 | 5-Methoxy-3-(2-piperidin-1-ylethyl)-1H-indole |
File:Mor-Tryptamine chemical structure.svg | Mor-T | artificial | H | ? | 3-[2-(Morpholin-4-yl)ethyl]-1H-indole | 25262-59-3
File:5-MeO-mor-T chemical structure.svg | 5-MeO-mor-T | artificial | 5-OCH3 | ? | 5-Methoxy-3-[2-(morpholin-4-yl)ethyl]-1H-indole | 3949-13-1
File:IsoqT chemical structure.svg | IsoqT[42] | artificial | H | ? | 3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-1H-indole |
File:5-MeO-IsoqT.svg | 5-MeO-IsoqT | artificial | 5-OCH3 | ? | 3-[2-(2-Azabicyclo[2.2.2]octan-2-yl)ethyl]-5-methoxy-1H-indole |
File:Indolylethylfentanyl.svg | Indolylethylfentanyl | artificial | H | (CH2)5-4-N(COCH2CH3)C6H5 | N-[1-[2-(1H-indol-3-yl)ethyl]piperidin-4-yl]-N-phenylpropanamide | 58399-46-5
| Methylethyltryptamine (MET)  | artificial  | H  | CH3 | CH2CH3 | N-Methyl-N-ethyltryptamine  | 5599-69-9
| Methylpropyltryptamine (MPT)  | artificial  | H  | CH3 | CH2CH2CH3 | N-Methyl-N-propyltryptamine  | 850032-72-3
| Methylisopropyltryptamine (MiPT)  | artificial  | H  | CH3 | CH(CH3)2 | N-Methyl-N-isopropyltryptamine  | 96096-52-5
File:Methylcyclopropyltryptamine.svg | Methylcyclopropyltryptamine (McPT)  | artificial  | H  | CH3 | C3H5 | N-Methyl-N-cyclopropyltryptamine  | 1373918-63-8
| Ethylcyclopropyltryptamine (EcPT)  | artificial  | H  | CH2CH3 | C3H5 | N-ethyl-N-cyclopropyltryptamine  |
| Propylcyclo­propyltryptamine (PcPT)  | artificial  | H  | CH2CH2CH3 | C3H5 | N-propyl-N-cyclopropyltryptamine  |
| Isopropylcyclo­propyltryptamine (iPcPT)  | artificial  | H  | CH(CH3)2 | C3H5 | N-isopropyl-N-cyclopropyltryptamine  |
| Dicyclopropyltryptamine (DcPT)  | artificial  | H  | C3H5 | C3H5 | N,N-dicyclopropyltryptamine  | 1373918-62-7
File:MBT.svg | Methylbutyltryptamine (MBT)  | artificial  | H  | CH3 | (CH2)3CH3 | N-Methyl-N-butyltryptamine  | 848130-12-1
File:MsBT structure.svg | Methyl-sec-butyltryptamine (MsBT)  | artificial  | H  | CH3 | CH(CH3)CH2CH3 | N-Methyl-N-sec-butyltryptamine  |
| Methylisobutyltryptamine (MiBT)  | artificial  | H  | CH3 | CH2CH(CH3)2 | N-Methyl-N-iso-butyltryptamine  |
| Methylcyclopropyl­methyltryptamine (McPMT)  | artificial  | H  | CH3 | CH2C3H5 | N-Methyl-N-(cyclopropylmethyl)tryptamine  |
File:Deudimethyltryptamine.svg | Deudimethyltryptamine (DMT-d10; likely CYB004)  | artificial  | H  | CH3 | CH3 | α,α,β,β-Tetradeutero-N,N-bis(trideuteriomethyl)tryptamine  | 2742678-60-8
File:D2-DMT structure.svg | SPL028 (D2-DMT)  | artificial  | H  | CH3 | CH3 | α,α-Dideutero-N,N-dimethyltryptamine  | ?
| Diethyltryptamine (DET)  | artificial  | H  | CH2CH3 | CH2CH3 | N,N-diethyltryptamine  | 61-51-8
| Ethylpropyltryptamine (EPT)  | artificial  | H  | CH2CH3 | CH2CH2CH3 | N-Ethyl-N-propyltryptamine  | 850032-68-7
| Ethylisopropyltryptamine (EiPT)  | artificial  | H  | CH2CH3 | CH(CH3)2 | N-Ethyl-N-isopropyltryptamine  | 848130-11-0
| Dipropyltryptamine (DPT)  | artificial  | H  | CH2CH2CH3 | CH2CH2CH3 | N,N-dipropyltryptamine  | 61-52-9
| Propylisopropyltryptamine (PiPT)  | artificial  | H  | CH2CH2CH3 | CH(CH3)2 | N-Propyl-N-isopropyltryptamine  | 1354632-00-0
| Diisopropyltryptamine (DiPT)  | artificial  | H  | CH(CH3)2 | CH(CH3)2 | N,N-diisopropyltryptamine  | 14780-24-6
| Ethylbutyltryptamine (EBT)  | artificial  | H  | CH2CH3 | (CH2)3CH3 | N-ethyl-N-butyltryptamine  |
| Propylbutyltryptamine (PBT)  | artificial  | H  | CH2CH2CH3 | (CH2)3CH3 | N-propyl-N-butyltryptamine  |
| Isopropyl-sec-butyltryptamine (iPsBT)  | artificial  | H  | CH(CH3)2 | CH(CH3)CH2CH3 | N-isopropyl-N-sec-butyltryptamine  |
| Dibutyltryptamine (DBT)  | artificial  | H  | (CH2)3CH3 | (CH2)3CH3 | N,N-dibutyltryptamine  | 15741-77-2
File:DiBT structure.svg | Diisobutyltryptamine (DiBT)  | artificial  | H  | CH2CH(CH3)2 | CH2CH(CH3)2 | N,N-diisobutyltryptamine  | 63938-64-7
File:DsBT structure.svg | Di-sec-butyltryptamine (DsBT)  | artificial  | H  | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | N,N-disecbutyltryptamine  |
File:Diamyltryptamine.svg | Diamyltryptamine (DAT)  | artificial  | H  | (CH2)4CH3 | (CH2)4CH3 | N,N-diamyltryptamine  |
File:Dihexyltryptamine.svg | Dihexyltryptamine (DHT)  | artificial  | H  | (CH2)5CH3 | (CH2)5CH3 | N,N-dihexyltryptamine  |
| Methylallyltryptamine (MALT)  | artificial  | H  | CH3 | H2C=CH-CH2 | N-methyl-N-allyltryptamine  | 1366416-29-6
File:DALT structure.svg | Diallyltryptamine (DALT)  | artificial  | H  | H2C=CH-CH2 | H2C=CH-CH2 | N,N-diallyltryptamine  | 60676-77-9
File:Propylallyltryptamine.svg | Propylallyltryptamine (PALT)  | artificial  | H  | H2C=CH-CH2 | CH2CH2CH3 | N-propyl-N-allyltryptamine  | 2686297-71-0
File:IPALT.svg | Isopropylallyltryptamine (iPALT, ALiPT)  | artificial  | H  | H2C=CH-CH2 | CH(CH3)2 | N-allyl-N-isopropyltryptamine  |
File:N-DEAOP-NMT chemical structure.svg | N-DEAOP-NMT | artificial  | H  | ?  | CH3 | N-(3-diethylamino-3-oxopropyl)-N-methyltryptamine  |
File:5-MeO-N-DEAOP-NMT chemical structure.svg | 5-MeO-N-DEAOP-NMT  | artificial  | 5-OCH3 | ?  | CH3 | N-(3-diethylamino-3-oxopropyl)-N-methyl-5-methoxytryptamine  |
File:N-DEAOP-NET chemical structure.svg | N-DEAOP-NET[43] | artificial  | H  | ?  | CH2CH3 | N-(3-diethylamino-3-oxopropyl)-N-ethyltryptamine  |
File:5-MeO-N-DEAOP-NET chemical structure.svg | 5-MeO-N-DEAOP-NET  | artificial  | 5-OCH3 | ?  | CH2CH3 | N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-methoxytryptamine  |
File:N-Phosphonooxymethyl-DMT.svg | N-Phosphonooxymethyl-DMT (N-POM-DMT)  | artificial  | H  | CH3 | CH3 | N-phosphonooxymethyl-N,N-dimethyltryptamine  | ?
File:N-Phosphonooxymethyl-5-MeO-DMT.svg | N-Phosphonooxymethyl-5-MeO-DMT (N-POM-5-MeO-DMT)  | artificial  | 5-OCH3 | CH3 | CH3 | 5-methoxy-N-phosphonooxymethyl-N,N-dimethyltryptamine  | ?
File:1-Methyl-DMT.svg | 1-Methyl-DMT | artificial  | 1-CH3 | CH3 | CH3 | 1-methyl-N,N-dimethyltryptamine  | 13366-47-7
| 2-Methyl-DMT | artificial  | 2-CH3 | CH3 | CH3 | (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine  | 1080-95-1
| 2-Methyl-DET | artificial  | 2-CH3 | CH2CH3 | CH2CH3 | N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine  | 26628-88-6
File:2-Methyl-DiPT chemical structure.svg | 2-Methyl-DiPT | artificial  | 2-CH3 | CH(CH3)2 | CH(CH3)2 | 2-methyl-N,N-diisopropyltryptamine  |
File:2-Methyl-iPALT.svg | 2-Methyl-iPALT | artificial  | 2-CH3 | CH(CH3)2 | H2C=CH-CH2 | 2-methyl-N-isopropyl-N-allyltryptamine  | 2915652-49-0
| 4-Amino-DMT [44] | artificial  | 4-NH2 | CH3 | CH3 | 4-amino-N,N-dimethyltryptamine  | 60331-61-5
File:4-Methyl-DMT.svg | 4-Methyl-DMT | artificial  | 4-CH3 | CH3 | CH3 | 4,N,N-trimethyltryptamine  | 28289-23-8
File:4-MeO-DMT chemical structure.svg | 4-MeO-DMT | artificial  | 4-OCH3 | CH3 | CH3 | 4-methoxy-N,N-dimethyltryptamine  | 3965-97-7
File:4-MeO-DET.svg | 4-MeO-DET | artificial  | 4-OCH3 | CH2CH3 | CH2CH3 | 4-methoxy-N,N-diethyltryptamine  |
| 4-MeO-MiPT | artificial  | 4-OCH3 | CH3 | CH(CH3)2 | 4-methoxy-N-methyl-N-isopropyltryptamine  | 96096-53-6
File:4-MeO-DiPT.svg | 4-MeO-DiPT | artificial  | 4-OCH3 | CH(CH3)2 | CH(CH3)2 | 4-methoxy-N,N-diisopropyltryptamine  |
File:Deupsilocin.svg | Deupsilocin (d10-psilocin; likely CYB003)  | artificial  | 4-OH  | CH3 | CH3 | 4-Hydroxy-α,α,β,β-Tetradeutero-N,N-bis(trideuteriomethyl)tryptamine  | 1435934-64-7
File:4-MeS-DMT.svg | 4-MeS-DMT | artificial  | 4-SCH3 | CH3 | CH3 | 4-methylthio-N,N-dimethyltryptamine  | 10455-77-3
File:4-AcO-DMT structure.svg | 4-AcO-DMT (psilacetin)  | artificial  | 4-OCOCH3 | CH3 | CH3 | 4-acetoxy-N,N-dimethyltryptamine  | 92292-84-7
| 4-PrO-DMT | artificial  | 4-OCOCH2CH3 | CH3 | CH3 | 4-propionyloxy-N,N-dimethyltryptamine  | 1373882-11-1
File:RE-109.svg | 4-GO-DMT (RE109; FT-109)  | artificial  | 4-OCO(CH2)3COOH  | CH3 | CH3 | 4-glutaryloxy-N,N-dimethyltryptamine  |
| 4-HO-MET (metocin)  | artificial  | 4-OH  | CH3 | CH2CH3 | 4-hydroxy-N-methyl-N-ethyltryptamine  | 77872-41-4
| 4-AcO-MET | artificial  | 4-OCOCH3 | CH3 | CH2CH3 | 4-acetoxy-N-methyl-N-ethyltryptamine  | 1445751-40-5
File:4-PrO-MET.svg | 4-PrO-MET | artificial  | 4-OCOCH2CH3 | CH3 | CH2CH3 | 4-propionyloxy-N-methyl-N-ethyltryptamine  |
| 4-PO-MET  | artificial  | 4-OPO3H2 | CH3 | CH2CH3 | 4-phosphoryloxy-N-methyl-N-ethyltryptamine  |
| 4-HO-DET (ethocin)  | artificial  | 4-OH  | CH2CH3 | CH2CH3 | 4-hydroxy-N,N-diethyltryptamine  | 22204-89-3
| 4-AcO-DET | artificial  | 4-OCOCH3 | CH2CH3 | CH2CH3 | 4-acetoxy-N,N-diethyltryptamine  | 1135424-15-5
File:Ethocybin.svg | 4-PO-DET (ethocybin)  | artificial  | 4-OPO3H2 | CH2CH3 | CH2CH3 | 4-phosphoryloxy-N,N-diethyltryptamine  | 60480-02-6
| 4-HO-EPT | artificial  | 4-OH  | CH2CH3 | CH2CH2CH3 | 4-hydroxy-N-ethyl-N-propyltryptamine  | 2595431-59-5
File:4-AcO-EPT.svg | 4-AcO-EPT | artificial  | 4-OCOCH3 | CH2CH3 | CH2CH2CH3 | 4-acetoxy-N-ethyl-N-propyltryptamine  | 2750249-90-0
| 4-PO-EPT  | artificial  | 4-OPO3H2 | CH2CH3 | CH2CH2CH3 | 4-phosphoryloxy-N-ethyl-N-propyltryptamine  |
| 4-AcO-EiPT | artificial  | 4-OCOCH3 | CH2CH3 | CH(CH3)2 | 4-acetoxy-N-ethyl-N-isopropyltryptamine  |
| 4-HO-MPT | artificial  | 4-OH  | CH3 | CH2CH2CH3 | 4-hydroxy-N-methyl-N-propyltryptamine  | 763035-03-6
File:4-AcO-MPT.svg | 4-AcO-MPT | artificial  | 4-OCOCH3 | CH3 | CH2CH2CH3 | 4-acetoxy-N-methyl-N-propyltryptamine  | 2173386-55-3
| 4-HO-MiPT | artificial  | 4-OH  | CH(CH3)2 | CH3 | 4-hydroxy-N-isopropyl-N-methyltryptamine  | 77872-43-6
| 4-AcO-MiPT | artificial  | 4-OCOCH3 | CH3 | CH(CH3)2 | 4-acetoxy-N-methyl-N-isopropyltryptamine  | 1024612-25-6
File:4-HO-MALT 2D.svg | 4-HO-MALT[45] | artificial  | 4-OH  | CH3 | H2C=CH-CH2 | 4-hydroxy-N-methyl-N-allyltryptamine  |
File:4-AcO-MALT.svg | 4-AcO-MALT[46] | artificial  | 4-OCOCH3 | CH3 | H2C=CH-CH2 | 4-acetoxy-N-Methyl-N-allyltryptamine  |
File:4-HO-iPALT chemical structure.svg | 4-HO-iPALT  | artificial  | 4-OH  | CH(CH3)2 | H2C=CH-CH2 | 4-hydroxy-N-isopropyl-N-allyltryptamine  |
File:4-HO-MBT.svg | 4-HO-MBT | artificial  | 4-OH  | (CH2)3CH3 | CH3 | 4-hydroxy-N-butyl-N-methyltryptamine  |
File:4-HO-MsBT.svg | 4-HO-MsBT  | artificial  | 4-OH  | CH(CH3)CH2CH3 | CH3 | 4-hydroxy-N-sec-butyl-N-methyltryptamine  |
File:4-HO-MtBT chemical structure.svg | 4-HO-MtBT  | artificial  | 4-OH  | C(CH3)3 | CH3 | 4-hydroxy-N-tert-butyl-N-methyltryptamine  |
File:4-HO-EiBT 2D.svg | 4-HO-EiBT | artificial[47] | 4-OH  | CH2CH(CH3)2 | CH2CH3 | 4-hydroxy-N-iso-butyl-N-ethyltryptamine  |
| 4-HO-McPT | artificial  | 4-OH  | C3H5 | CH3 | 4-hydroxy-N-cyclopropyl-N-methyltryptamine  | 2883663-05-4
File:4-AcO-McPT.svg | 4-AcO-McPT | artificial  | 4-OCOCH3 | C3H5 | CH3 | 4-acetoxy-N-cyclopropyl-N-methyltryptamine  |
| 4-HO-McPeT | artificial  | 4-OH  | C5H9 | CH3 | 4-hydroxy-N-cyclopentyl-N-methyltryptamine  | 77872-48-1
File:4-HO-McPMT structure.png | 4-HO-McPMT [48] | artificial  | 4-OH  | CH2C3H5 | CH3 | 4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine  |
| 4-HO-DPT | artificial  | 4-OH  | CH2CH2CH3 | CH2CH2CH3 | 4-hydroxy-N,N-dipropyltryptamine  | 63065-88-3
| 4-AcO-DPT | artificial  | 4-OCOCH3 | CH2CH2CH3 | CH2CH2CH3 | 4-acetoxy-N,N-dipropyltryptamine  | 1445751-75-6
artificial  | 4-MeCO3 | CH2CH2CH3 | CH2CH2CH3 | 4-methylcarbonato-N,N-dipropyltryptamine  | ?
| 4-HO-PiPT | artificial  | 4-OH  | CH2CH2CH3 | CH(CH3)2 | 4-hydroxy-N-propyl-N-isopropyltryptamine  |
File:4-AcO-PiPT structure.png | 4-AcO-PiPT  | artificial  | 4-OCOCH3 | CH2CH2CH3 | CH(CH3)2 | 4-acetoxy-N-propyl-N-isopropyltryptamine  |
| 4-HO-DiPT | artificial  | 4-OH  | CH(CH3)2 | CH(CH3)2 | 4-hydroxy-N,N-diisopropyltryptamine  | 132328-45-1
| 4-AcO-DiPT | artificial  | 4-OCOCH3 | CH(CH3)2 | CH(CH3)2 | 4-acetoxy-N,N-diisopropyltryptamine  | 936015-60-0
File:4-PrO-DiPT.svg | 4-PrO-DiPT | artificial  | 4-OCOCH2CH3 | CH(CH3)2 | CH(CH3)2 | 4-propionyloxy-N,N-diisopropyltryptamine  | 1373882-13-3
File:Luvesilocin structure.svg | Luvesilocin (RE104; FT-104)  | artificial  | 4-OCO(CH2)3COOH  | CH(CH3)2 | CH(CH3)2 | 4-glutaryloxy-N,N-diisopropyltryptamine  |
| 4-PO-DiPT  | artificial  | 4-OPO3H2 | CH(CH3)2 | CH(CH3)2 | 4-phosphoryloxy-N,N-diisopropyltryptamine  | 1373882-09-7
File:4-HO-DALT 2D.svg | 4-HO-DALT | artificial  | 4-OH  | H2C=CH-CH2 | H2C=CH-CH2 | 4-hydroxy-N,N-diallyltryptamine  | 2173386-70-2
| 4-AcO-DALT | artificial  | 4-OCOCH3 | H2C=CH-CH2 | H2C=CH-CH2 | 4-acetoxy-N,N-diallyltryptamine  | 1445751-71-2
| 4-HO-DBT | artificial  | 4-OH  | (CH2)3CH3 | (CH2)3CH3 | 4-hydroxy-N,N-dibutyltryptamine  | 63065-89-4
File:4-HO-DiBT.svg | 4-HO-DiBT  | artificial  | 4-OH  | CH2CH(CH3)2 | CH2CH(CH3)2 | 4-hydroxy-N,N-diisobutyltryptamine  |
| 4-HO-DsBT  | artificial  | 4-OH  | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | 4-hydroxy-N,N-disecbutyltryptamine  | 127507-01-1
File:4-Fluoro-DMT.svg | 4-Fluoro-DMT | artificial  | 4-F  | CH3 | CH3 | 4-fluoro-N,N-dimethyltryptamine  | 1644-64-0
File:5-MeO-DMT-d4.svg | 5-MeO-DMT-d4 (α,α,β,β-tetradeutero-5-MeO-DMT)  | artificial  | 5-OCH3 | CH3 | CH3 | α,α,β,β-Tetradeutero-5-methoxy-N,N-dimethyltryptamine  | 66521-37-7
| 5-MeO-MET | artificial  | 5-OCH3 | CH2CH3 | CH3 | 5-methoxy-N-methyl-N-ethyltryptamine  | 16977-53-0
| 5-MeO-DET | artificial  | 5-OCH3 | CH2CH3 | CH2CH3 | 5-methoxy-N,N-diethyltryptamine  | 2454-70-8
File:5-MeO-MPT 2D.svg | 5-MeO-MPT | artificial  | 5-OCH3 | CH3 | CH2CH2CH3 | 5-methoxy-N-methyl-N-propyltryptamine  |
File:5-MeO-EPT structure.svg | 5-MeO-EPT | artificial  | 5-OCH3 | CH2CH3 | CH2CH2CH3 | 5-methoxy-N-ethyl-N-propyltryptamine  | 850032-67-6
| 5-MeO-DPT | artificial  | 5-OCH3 | CH2CH2CH3 | CH2CH2CH3 | 5-methoxy-N,N-dipropyltryptamine  | 69496-75-9
File:5-MeO-MALT.svg | 5-MeO-MALT | artificial  | 5-OCH3 | H2C=CH-CH2 | CH3 | 5-methoxy-N-Methyl-N-allyltryptamine  | 1373918-64-9
| 5-MeO-DALT | artificial  | 5-OCH3 | H2C=CH-CH2 | H2C=CH-CH2 | 5-methoxy-N,N-diallyltryptamine  | 928822-98-4
File:5-MeO-iPALT 2D.svg | ASR-3001 (5-MeO-iPALT)  | artificial  | 5-OCH3 | H2C=CH-CH2 | CH2CH(CH3)2 | 5-methoxy-N-allyl-N-isopropyltryptamine  |
| 5-MeO-MiPT | artificial  | 5-OCH3 | CH3 | CH(CH3)2 | 5-methoxy-N,N-methylisopropyltryptamine  | 96096-55-8
| 5,6-MeO-MiPT | artificial  | 5-OCH3, 6-OCH3 | CH3 | CH(CH3)2 | 5,6-dimethoxy-N,N-methylisopropyltryptamine  |
File:5-MeO-MBT.svg | 5-MeO-MBT | artificial  | 5-OCH3 | CH3 | (CH2)3CH3 | 5-methoxy-N-methyl-N-butyltryptamine  |
File:5-MeO-MsBT.svg | 5-MeO-MsBT | artificial  | 5-OCH3 | CH3 | CH(CH3)CH2CH3 | 5-methoxy-N-methyl-N-sec-butyltryptamine  |
| 5-MeO-McPT  | artificial  | 5-OCH3 | CH3 | C3H5 | 5-methoxy-N-methyl-N-cyclopropyltryptamine  |
| 5-MeO-McBT  | artificial  | 5-OCH3 | CH3 | C4H7 | 5-methoxy-N-methyl-N-cyclobutyltryptamine  |
File:5-MeO-EiPT.svg | 5-MeO-EiPT | artificial  | 5-OCH3 | CH2CH3 | CH(CH3)2 | 5-methoxy-N-ethyl-N-isopropyltryptamine  | 850032-66-5
| 5-MeO-PiPT | artificial  | 5-OCH3 | CH2CH2CH3 | CH(CH3)2 | 5-methoxy-N-propyl-N-isopropyltryptamine  |
| 5-MeO-DiPT | artificial  | 5-OCH3 | CH(CH3)2 | CH(CH3)2 | 5-methoxy-N,N-diisopropyltryptamine  | 4021-34-5
| 5-MeO-DBT | artificial  | 5-OCH3 | (CH2)3CH3 | (CH2)3CH3 | 5-methoxy-N,N-dibutyltryptamine  | 73785-42-9
File:5-MeO-DsBT.svg | 5-MeO-DsBT | artificial  | 5-OCH3 | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | 5-methoxy-N,N-di-sec-butyltryptamine  |
| 5-MeS-DMT | artificial  | 5-SCH3 | CH3 | CH3 | 5-methylthio-N,N-dimethyltryptamine  | 5102-11-4
| 5-AcO-DMT (O-acetylbufotenine)  | artificial  | 5-OCOCH3 | CH3 | CH3 | 5-acetoxy-N,N-dimethyltryptamine  | 16977-50-7
File:O-Pivalylbufotenine.svg | 5-t-BuCO-DMT (O-pivalylbufotenine)  | artificial  | ?  | CH3 | CH3 | 5-pivaloxy-N,N-dimethyltryptamine  | ?
| 5-AcO-MET [49] | artificial  | 5-OCOCH3 | CH3 | CH2CH3 | 5-acetoxy-N-methyl-N-ethyltryptamine  |
| 5-AcO-DET  | artificial  | 5-OCOCH3 | CH2CH3 | CH2CH3 | 5-acetoxy-N,N-diethyltryptamine  |
| 5-AcO-EPT [50] | artificial  | 5-OCOCH3 | CH2CH3 | CH2CH2CH3 | 5-acetoxy-N-ethyl-N-propyltryptamine  |
| 5-AcO-DPT  | artificial  | 5-OCOCH3 | CH2CH2CH3 | CH2CH2CH3 | 5-acetoxy-N,N-dipropyltryptamine  |
| 5-AcO-MiPT  | artificial  | 5-OCOCH3 | CH3 | CH(CH3)2 | 5-acetoxy-N-methyl-N-isopropyltryptamine  |
| 5-AcO-DiPT  | artificial  | 5-OCOCH3 | CH(CH3)2 | CH(CH3)2 | 5-acetoxy-N,N-diisopropyltryptamine  |
| 5-Ethoxy-DMT | artificial | 5-OCH2CH3 | CH3 | CH3 | 5-ethoxy-N,N-dimethyltryptamine | 855245-09-9
| 5-Ethoxy-MET | artificial | 5-OCH2CH3 | CH3 | CH2CH3 | 5-ethoxy-N-methyl-N-ethyltryptamine |
| 5-Ethoxy-DET | artificial | 5-OCH2CH3 | CH2CH3 | CH2CH3 | 5-ethoxy-N,N-diethyltryptamine |
| 5-Ethoxy-MPT | artificial | 5-OCH2CH3 | CH3 | CH2CH2CH3 | 5-ethoxy-N-methyl-N-propyltryptamine |
| 5-Ethoxy-EPT | artificial | 5-OCH2CH3 | CH2CH3 | CH2CH2CH3 | 5-ethoxy-N-ethyl-N-propyltryptamine |
| 5-Ethoxy-DPT | artificial | 5-OCH2CH3 | CH2CH2CH3 | CH2CH3 | 5-ethoxy-N,N-dipropyltryptamine |
| 5-Ethoxy-MiPT | artificial | 5-OCH2CH3 | CH3 | CH(CH3)2 | 5-ethoxy-N-methyl-N-isopropyltryptamine |
| 5-Ethoxy-EiPT | artificial | 5-OCH2CH3 | CH2CH3 | CH(CH3)2 | 5-ethoxy-N-ethyl-N-isopropyltryptamine |
| 5-Ethoxy-DiPT | artificial | 5-OCH2CH3 | CH(CH3)2 | CH(CH3)2 | 5-ethoxy-N,N-diisopropyltryptamine |
| 5-Ethoxy-DALT | artificial | 5-OCH2CH3 | H2C=CH-CH2 | H2C=CH-CH2 | 5-ethoxy-N,N-diallyltryptamine |
| 5-BnO-DMT  | artificial  | 5-OCH2C6H5 | CH3 | CH3 | 5-benzyloxy-N,N-dimethyltryptamine  | 101832-88-6
File:5-OH-MET.svg | 5-HO-MET | artificial  | 5-OH  | CH3 | CH2CH3 | 5-hydroxy-N-methyl-N-ethyltryptamine  | 1443666-13-4
File:5-HO-DET 2D.svg | 5-HO-DET | artificial  | 5-OH  | CH2CH3 | CH2CH3 | 5-hydroxy-N,N-diethyltryptamine  | 14009-42-8
File:Dipropylserotonin.svg | 5-HO-DPT  | artificial  | 5-OH  | CH2CH2CH3 | CH2CH2CH3 | 5-hydroxy-N,N-dipropyltryptamine  | 36288-75-2
File:5-HO-MiPT.svg | 5-HO-MiPT  | artificial  | 5-OH  | CH3 | CH(CH3)2 | 5-hydroxy-N-methyl-N-isopropyltryptamine  |
| 5-HO-DiPT | artificial  | 5-OH  | CH(CH3)2 | CH(CH3)2 | 5-hydroxy-N,N-diisopropyltryptamine  | 36288-76-3
| 5-Methyl-DMT (5,N,N-TMT) | artificial | 5-CH3 | CH3 | CH3 | 5,N,N-trimethyltryptamine | 22120-39-4
File:5-Ethyl-DMT.svg | 5-Ethyl-DMT | artificial | 5-CH2CH3 | CH3 | CH3 | 5-ethyl-N,N-dimethyltryptamine | 171783-25-8
| 5-Isopropyl-DMT | artificial | 5-CH(CH3)2 | CH3 | CH3 | 5-isopropyl-N,N-dimethyltryptamine | 156281-04-8
| 5-(t-Butyl)-DMT [51] | artificial | 5-C(CH3)3 | CH3 | CH3 | 5-(tert-butyl)-N,N-dimethyltryptamine |
File:5-Fluoro-DMT.svg | 5-Fluoro-DMT | artificial | 5-F | CH3 | CH3 | 5-fluoro-N,N-dimethyltryptamine | 22120-36-1
| Bretisilocin (5-fluoro-MET; GM-2505) | artificial | 5-F | CH3 | CH2CH3 | 5-fluoro-N-methyl-N-ethyltryptamine | 2698331-35-8
| 5-Fluoro-DET | artificial | 5-F | CH2CH3 | CH2CH3 | 5-fluoro-N,N-diethyltryptamine |
| 5-Fluoro-EPT | artificial | 5-F | CH2CH3 | CH2CH2CH3 | 5-fluoro-N-ethyl-N-propyltryptamine |
| 5-Fluoro-DPT | artificial | 5-F | CH2CH2CH3 | CH2CH2CH3 | 5-fluoro-N,N-dipropyltryptamine |
| 5-Fluoro-PiPT | artificial | 5-F | CH2CH2CH3 | CH(CH3)2 | 5-fluoro-N-propyl-N-isopropyltryptamine |
| 5-Fluoro-PcBT | artificial | 5-F | CH2CH2CH3 | CH(CH2)3 | 5-fluoro-N-propyl-N-cyclobutyltryptamine |
| 5-Fluoro-iPcBT | artificial | 5-F | CH(CH3)2 | CH(CH2)3 | 5-fluoro-N-isopropyl-N-cyclobutyltryptamine |
| 5-Fluoro-DiPT | artificial | 5-F | CH(CH3)2 | CH(CH3)2 | 5-fluoro-N,N-diisoproptryptamine |
| 5-Fluoro-sBALT | artificial | 5-F | CH(CH3)CH2CH3 | CH2CH=CH2 | 5-fluoro-N-sec-butyl-N-allyltryptamine |
| 5-Fluoro-M1MALT | artificial | 5-F | CH3 | CH(CH3)CH=CH2 | 5-fluoro-N-methyl-N-(1-methylallyl)tryptamine |
| 5-Chloro-DMT | artificial | 5-Cl | CH3 | CH3 | 5-chloro-N,N-dimethyltryptamine | 22120-32-7
File:5-Iodo-DMT.svg | 5-Iodo-DMT | artificial | 5-I | CH3 | CH3 | 5-iodo-N,N-dimethyltryptamine | 22120-38-3
File:5-TFM-DMT 2D.svg | 5-TFM-DMT | artificial | 5-CF3 | CH3 | CH3 | 5-(trifluoromethyl)-N,N-dimethyltryptamine | 2418713-32-1
File:5-TFMO-DMT 2D.svg | 5-TFMO-DMT[52] | artificial | 5-OCF3 | CH3 | CH3 | 5-(trifluoromethoxy)-N,N-dimethyltryptamine |
File:5-Nitro-DMT 2D.svg | 5-Nitro-DMT[53] | artificial | 5-NO2 | CH3 | CH3 | 5-nitro-N,N-dimethyltryptamine | 69937-13-9
| 5-CN-DMT | artificial | 5-C≡N | CH3 | CH3 | 5-cyano-N,N-dimethyltryptamine | 17380-42-6
| 5-CN-DPT | artificial | 5-C≡N | CH2CH2CH3 | CH2CH2CH3 | 5-cyano-N,N-dipropyltryptamine | 74885-19-1
| Almotriptan | artificial  | 5-(CH2SO2N(CH2)4)  | CH3 | CH3 | N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine  | 154323-57-6
| Rizatriptan | artificial  | 5-(CH2(N3(CH)2))  | CH3 | CH3 | N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine  | 145202-66-0
| Sumatriptan | artificial  | 5-(CH2SO2NHCH3)  | CH3 | CH3 | 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide  | 103628-46-2
| Zolmitriptan | artificial  | 5-(CHNHC=OOCH2)  | CH3 | CH3 | 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine  | 139264-17-8
File:6-Fluoro-DMT structure.svg | 6-Fluoro-DMT | artificial | 6-F | CH3 | CH3 | 6-fluoro-N,N-dimethyltryptamine | 1511-31-5
| 6-Fluoro-DET[54] | artificial | 6-F | CH2CH3 | CH2CH3 | 6-fluoro-N,N-diethyltryptamine | 2836-69-3
| 6-Chloro-DMT | artificial | 6-Cl | CH3 | CH3 | 6-chloro-N,N-dimethyltryptamine | 25390-72-1
File:6-Methyl-DMT.svg | 6-Methyl-DMT | artificial | 6-CH3 | CH3 | CH3 | 6,N,N-trimethyltryptamine |
File:6-Hydroxy-DMT.svg | 6-Hydroxy-DMT | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-dimethyltryptamine | 1476-33-1
File:6-HO-DET 2D.svg | 6-Hydroxy-DET | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-diethyltryptamine | 1476-59-1
File:6-MeO-DMT.svg | 6-Methoxy-DMT | artificial | 6-OCH3 | CH3 | CH3 | 6-methoxy-N,N-dimethyltryptamine | 2426-88-2
File:6-TFMO-DMT.svg | 6-TFMO-DMT (6-trifluoromethoxy-DMT)[55][56][57] | artificial | 6-OCF3 | CH3 | CH3 | 6-trifluoromethoxy-N,N-dimethyltryptamine |
| 7-Methyl-DMT | artificial | 7-CH3 | CH3 | CH3 | 7,N,N-trimethyltryptamine | 65882-39-5
| 7-Ethyl-DMT | artificial | 7-CH2CH3 | CH3 | CH3 | 7-ethyl-N,N-dimethyltryptamine |
| 7-Chloro-DMT | artificial | 7-Cl | CH3 | CH3 | 7-chloro-N,N-dimethyltryptamine |
| 7-Bromo-DMT[58] | artificial | 7-Br | CH3 | CH3 | 7-bromo-N,N-dimethyltryptamine | 74798-68-8
File:7-Hydroxy-DMT.svg | 7-Hydroxy-DMT | artificial | 7-OH | CH3 | CH3 | 7-hydroxy-N,N-dimethyltryptamine | 7578-26-9
| 7-Methoxy-DMT | artificial | 7-OCH3 | CH3 | CH3 | 7-methoxy-N,N-dimethyltryptamine |
| 7-Methoxy-MiPT | artificial | 7-OCH3 | CH3 | CH(CH3)2 | 7-methoxy-N-methyl-N-isopropyltryptamine |
| 1-Methylpsilocin | artificial  | 1-CH3, 4-OH  | CH3 | CH3 | 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole  | 1465-16-3
File:1-Ethylpsilocin structure.png | 1-Ethylpsilocin [59] | artificial  | 1-CH2CH3, 4-OH  | CH3 | CH3 | 1-Ethyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole  | 1640-02-4
| 1-Methyl-5-MeO-DiPT  | artificial  | 1-CH3, 5-OCH3 | CH(CH3)2 | CH(CH3)2 | 1-methyl-5-methoxy-N,N-diisopropyltryptamine  | 1373882-10-0
File:1-Acetyl-DMT.svg | 1-Acetyl-DMT (1A-DMT; DMT AР-1)[60][61][62] | artificial  | 1-COCH3 | CH3 | CH3 | 1-acetyl-N,N-dimethyltryptamine  | 39998-62-4
File:1-Benzoyl-DMT.svg | 1-Benzoyl-DMT (1Bz-DMT)  | artificial  | 1-COC6H5 | CH3 | CH3 | 1-benzoyl-N,N-dimethyltryptamine  | 481661-45-4
File:NB-DMT.svg | NBoc-DMT (NB-DMT)  | artificial  | 1-OCOC(CH3)3 | CH3 | CH3 | 1-(t-butoxycarbonyl)-N,N-dimethyltryptamine  | 2210243-51-7
File:1-Acetyl-5-MeO-DMT.svg | 1-Acetyl-5-MeO-DMT (1A-5-MeO-DMT)[63][61][62] | artificial  | 1-COCH3, 5-OCH3 | CH3 | CH3 | 1-acetyl-5-methoxy-N,N-dimethyltryptamine  | 39998-63-5
File:NB-5-MeO-DMT.svg | NB-5-MeO-DMT[64] | artificial  | 1-OCOC(CH3)3, 5-OCH3 | CH3 | CH3 | 1-(t-butoxycarbonyl)-5-methoxy-N,N-dimethyltryptamine  |
File:NB-5-MeO-MiPT.svg | NB-5-MeO-MiPT | artificial  | 1-OCOC(CH3)3, 5-OCH3 | CH3 | CH(CH3)2 | 1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine  |
File:NB-5-MeO-DALT.svg | NB-5-MeO-DALT | artificial  | 1-OCOC(CH3)3, 5-OCH3 | H2C=CH-CH2 | H2C=CH-CH2 | 1-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine  |
File:7-Methylpsilocin.svg | 7-Methylpsilocin (see BMB-A39a)[65][66] | artificial | 4-OH,7-Me | CH3 | CH3 | 4-hydroxy-7-methyl-N,N-dimethyltryptamine | 2770305-95-6
File:7-Methylpsilocybin.svg | 7-Methylpsilocybin (see BMB-201)[67][65] | artificial | 4-PO,7-Me | CH3 | CH3 | 4-phosphoryloxy-7-methyl-N,N-dimethyltryptamine | ?
| 6-Fluoropsilocin | artificial | 4-OH,6-F | CH3 | CH3 | 4-hydroxy-6-fluoro-N,N-dimethyltryptamine | 312314-12-8
File:6-Fluoro-7-methylpsilocin structure.png | 6-Fluoro-7-methylpsilocin [68] | artificial | 4-OH,6-F,7-Me | CH3 | CH3 | 4-hydroxy-6-fluoro-7-methyl-N,N-dimethyltryptamine | 2873459-44-8
| 6-Fluoro-5-MeO-DMT | artificial | 5-OCH3,6-F | CH3 | CH3 | 5-methoxy-6-fluoro-N,N-dimethyltryptamine |
| 5,6-Difluoro-EPT | artificial | 5-F, 6-F | CH2CH3 | CH2CH2CH3 | 5,6-difluoro-N-ethyl-N-propyltryptamine |
| 5-MeO-2-TMT | artificial  | 2-CH3, 5-OCH3 | CH3 | CH3 | 2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine  | 67292-68-6
File:5-MeO-4-TMT.svg | 5-MeO-4-TMT  | artificial  | 4-CH3, 5-OCH3 | CH3 | CH3 | 5-Methoxy-4,N,N-trimethyltryptamine  |
File:6-Methyl-5-MeO-DMT.svg | 5-MeO-6-TMT (P-42)  | artificial  | 5-OCH3, 6-CH3 | CH3 | CH3 | 5-Methoxy-6,N,N-trimethyltryptamine  |
File:5-MeO-7-TMT 2D.svg | 5-MeO-7-TMT (P-51)  | artificial  | 5-OCH3, 7-CH3 | CH3 | CH3 | 5-Methoxy-7,N,N-trimethyltryptamine  | 61018-77-7
| 4-HO-5-MeO-DMT (psilomethoxin)  | artificial  | 4-OH, 5-OCH3 | CH3 | CH3 | 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine  | 2433-31-0
File:5-Methylpsilocin.svg | 5-Methylpsilocin (P-10)  | artificial  | 4-HO, 5-CH3 | CH3 | CH3 | 4-Hydroxy-5-methyl-N,N-dimethyltryptamine  |
File:5-Methylpsilocybin structure.svg | 5-Methylpsilocybin (5-Me-4-PO-DMT)  | artificial  | 4-PO, 5-CH3 | CH3 | CH3 | 4-Phosphoryloxy-5-methyl-N,N-dimethyltryptamine  | ?
File:5-Methoxypsilocybin.svg | 4-PO-5-MeO-DMT (5-methoxypsilocybin)  | artificial  | 4-PO, 5-OCH3 | CH3 | CH3 | 4-Phosphoryloxy-5-methoxy-N,N-dimethyltryptamine  | ?
| 4-F-5-MeO-DMT | artificial  | 4-F, 5-OCH3 | CH3 | CH3 | 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine  | 312314-18-4
File:5-Me-4-HO-MiPT structure.png | 5-Me-4-HO-MiPT (P-66)  | artificial  | 4-HO, 5-CH3 | CH3 | CH(CH3)2 | 4-Hydroxy-5-Methyl-N-methyl-N-isopropyltryptamine  |
File:7-Me-4-HO-DPT structure.png | 7-Me-4-HO-DPT (P-89)  | artificial  | 4-HO, 7-CH3 | CH2CH2CH3 | CH2CH2CH3 | 4-Hydroxy-7-Methyl-N,N-dipropyltryptamine  |
File:7-F-5-MeO-MET 2D.svg | 5-MeO-7-F-MET  | artificial  | 5-OCH3, 7-F  | CH3 | CH2CH3 | 5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine  |
File:HBL20017.svg | HBL20017 (4-F-5-MeS-DMT)  | artificial  | 4-F, 5-SCH3 | CH3 | CH3 | 4-Fluoro-5-methylthio-N,N-dimethyltryptamine  | ?
File:HBL20016.svg | HBL20016 (5-MeS-6-F-DMT)  | artificial  | 5-SCH3, 6-F  | CH3 | CH3 | 5-Methylthio-6-fluoro-N,N-dimethyltryptamine  | ?
| EMDT (2-ethyl-5-MeO-DMT)  | artificial  | 2-CH2CH3, 5-OCH3 | CH3 | CH3 | 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine  | 263744-72-5
| ST-1936 (2-methyl-5-chloro-DMT)  | artificial  | 2-CH3, 5-Cl  | CH3 | CH3 | 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine  | 1210-81-7
File:Benanserin.svg | Benanserin (benzyl antiserotonin; BAS; MC-4788; Sq-4788)  | artificial  | 1-CH2C6H5, 2-CH3, 5-OCH3 | H  | H  | 2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine  | 441-91-8
| O-4310 (1-isopropyl-6-fluoropsilocin)  | artificial  | 1-CH(CH3)2, 4-OH, 6-F  | CH3 | CH3 | 3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol  | 885671-63-6
File:Indorenate.svg | Indorenate (TR-3369)  | artificial  | 5-OCH3, β-COOCH3 | H  | H  | β-Methoxycarbonyl-5-methoxytryptamine  | 73758-06-2
| CP-132,484 (4,5-DHP-1-Me-T)  | artificial  | 1-methyl-4,5-(OCH2CH2CH2)  | H  | H  | 1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole  | 143508-76-3
| 4,5-DHP-DMT | artificial  | 4,5-(OCH2CH2CH2)  | CH3 | CH3 | 1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole  | 135360-97-3
| 4,5-DHF-DMT (P-3)  | artificial[69] | 4,5-(CH2CH2O)  | CH3 | CH3 | 2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine  |
| 4,5-Methylbenzoxazole-DMT (P-131)  | artificial  | 4,5-(OC(CH3)=N)  | CH3 | CH3 | N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine  |
| 4,5-MDO-DMT | artificial  | 4,5-(OCH2O)  | CH3 | CH3 | 2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine  | 81249-30-1
| 4,5-MDO-DiPT | artificial  | 4,5-(OCH2O)  | CH(CH3)2 | CH(CH3)2 | N-[2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine  | 82173-82-8
| 5,6-FUR-DMT (P-4)  | artificial  | 5,6-(CH=CHO)  | CH3 | CH3 | 2-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine  |
| 5,6-MDO-DMT | artificial  | 5,6-(OCH2O)  | CH3 | CH3 | 2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine  |
| 5,6-MDO-MiPT | artificial  | 5,6-(OCH2O)  | CH3 | CH(CH3)2 | N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine  |
| 5,6-MDO-DiPT | artificial  | 5,6-(OCH2O)  | CH(CH3)2 | CH(CH3)2 | N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine  |

### List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen.[70][71][72] α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life.[72] This is analogous to α-methylation of phenethylamine into amphetamine.[72]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[73][74][75][76] and produce psychostimulant, entactogen, and/or psychedelic effects.[70][71][72] The most well-known of these agents are α-methyltryptamine (AMT) and α-ethyltryptamine (AET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[71][72] In accordance with its action as a dual releasing agent of serotonin and dopamine, AET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as AMT, 5-MeO-AMT, and various others.[77]

Template:Sticky

Structure  | Name  | Chemical name  | CAS #

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File:Tryptophan alt.svg | Tryptophan | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid  | 73-22-3
File:5-Hydroxytryptophan alt.svg | 5-Hydroxytryptophan (5-HTP)  | (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid  | 4350-09-8
File:5-Methoxytryptophan alt.svg | 5-Methoxytryptophan (5-MTP)  | (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid  | 2504-22-5
File:Α-Methyltryptophan.svg | α-Methyltryptophan | (2S)-2-amino-3-(1H-indol-3-yl)-2-methylpropanoic acid  | 16709-25-4
File:Α-Methyl-5-hydroxytryptophan.svg | α-Methyl-5-HTP  | (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)-2-methylpropanoic acid  | 150852-19-0
File:Α-Methyl-5-methoxytryptophan.svg | α-Methyl-5-MTP  | (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)-2-methylpropanoic acid  | ?
| AMT (αMT; α-MT; Indopan)  | 1-(1H-Indol-3-yl)propan-2-amine  | 299-26-3
| 2,α-DMT (2-methyl-AMT)  | 1-(2-methyl-1H-indol-3-yl)propan-2-amine  | 4966-28-3
File:4-Methyl-AMT.svg | 4-Methyl-AMT  | 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine  | 3569-29-7
File:5-Fluoro-AMT.svg | 5-Fluoro-AMT | 1-(5-fluoro-1H-indol-3-yl)propan-2-amine  | 712-08-3
| 5-Chloro-AMT  | 1-(5-Chloro-1H-indol-3-yl)propan-2-amine  | 712-07-2
File:Alpha-methylserotonin.svg | 5-HO-AMT (αMS/α-methyl-5-HT)  | 3-(2-aminopropyl)-1H-indol-5-ol  | 304-52-9
| 5-MeO-AMT | 1-(5-methoxy-1H-indol-3-yl)propan-2-amine  | 1137-04-8
| 5-Ethoxy-AMT  | 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine  | 101832-83-1
| 5-Isopropoxy-AMT  | 1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine  |
File:5-Allyloxy-AMT.svg | 5-Allyloxy-AMT | 1-{5-[(prop-2-en-1-yl)oxy]-1H-indol-3-yl}propan-2-amine  |
File:1-Propyl-5-MeO-AMT structure.svg | 1-Propyl-5-MeO-AMT | 1-(5-methoxy-1-propylindol-3-yl)propan-2-amine  | ?
| BW-723C86 | 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine  | 160521-72-2
File:6-fluoro-AMT.svg | 6-Fluoro-AMT | 1-(6-fluoro-1H-indol-3-yl)propan-2-amine  | 712-11-8
| 7-Chloro-AMT | 1-(7-chloro-1H-indol-3-yl)propan-2-amine  | 711-99-9
| AL-37350A (4,5-DHP-AMT)  | (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole  | 362603-40-5
| Compound 5 [78] | 1-(3H-benzo[e]indol-1-yl)propan-2-amine  |
| AET (αET; α-ET)  | 1-(1H-indol-3-yl)butan-2-amine  | 2235-90-7
File:4-Methyl-AET.svg | 4-Methyl-AET  | 1-(4-Methyl-1H-indol-3-yl)butan-2-amine  | 28289-30-7
File:4-HO-AET 2D.svg | 4-HO-AET  | 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine  | 28289-28-3
| 5-Fluoro-AET | 1-(5-fluoro-1H-indol-3-yl)butan-2-amine  | 1380137-98-3
File:5-Chloro-AET.svg | 5-Chloro-AET  | 1-(5-chloro-1H-indol-3-yl)butan-2-amine  | ?
| 5-Methyl-AET  | 1-(5-methyl-1H-indol-3-yl)butan-2-amine  | 1380148-21-9
| 5-MeO-AET | 1-(5-methoxy-1H-indol-3-yl)butan-2-amine  | 4765-10-0
| 7-Methyl-AET  | 1-(7-methyl-1H-indol-3-yl)butan-2-amine  | 13712-80-6
| α,N-DMT (SK&F-7024, Ro 3-1715; N-methyl-AMT)  | 1-(1H-indol-3-yl)-N-methylpropan-2-amine  | 299-24-1
| N,N-Dimethyl-AMT (α,N,N-TMT)  | (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine  | 4761-32-4
File:N-Hydroxy-AMT.svg | N-Hydroxy-AMT (N-HO-AMT)  | N-[1-(1H-indol-3-yl)propan-2-yl]hydroxylamine  | 63-33-2
| N-Methyl-5-MeO-AMT (α,N,O-TMS/α,N,O-trimethyl-5-HT)  | [1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine  | 4822-13-3
File:Alpha,N,N,O-tetramethylserotonin.svg | N,N-Dimethyl-5-MeO-AMT (5-MeO-α,N,N-TMT)  | (2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine  | 101831-90-7
File:Alpha-propyl-tryptamine.svg | α-Propyltryptamine (APT; αPT; α-PT)  | 1-(1H-indol-3-yl)pentan-2-amine  |
File:Indolylpropylaminopentane.svg | Indolylpropylaminopentane (IPAP; α,N-DPT)  | 1-(1H-indol-3-yl)-N-propylpentan-2-amine  |
| α-Methyl-DiPT  | (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine  |
| MPMI[79] | 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole  | 143321-54-4
File:Lucigenol (4-HO-MPMI).svg | Lucigenol (4-HO-MPMI)  | 3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole  | ?
| 5-MeO-MPMI (CP-108509)  | 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole  | 143321-57-7
File:5-Fluoro-MPMI.svg | 5-Fluoro-MPMI[80] | 5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole  | ?
File:5-Bromo-MPMI.svg | 5-Bromo-MPMI  | 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole  | 143322-57-0
| Eletriptan | 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole  | 143322-58-1
File:Z5247692566.svg | Z5247692566[40][81] | 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine  |
| BK-NM-AMT (α,N-dimethyl-β-ketotryptamine)[82][83][84] | 1-(1H-indol-3-yl)-2-(methylamino)propan-1-one  |
File:BK-5F-NM-AMT.svg | BK-5F-NM-AMT (5-fluoro-α,N-dimethyl-β-ketotryptamine)[85][86][87][84] | 1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one  |
File:BK-5Cl-NM-AMT.svg | BK-5Cl-NM-AMT (5-chloro-α,N-dimethyl-β-ketotryptamine)[87][88][89] | 1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one  |
File:BK-5Br-NM-AMT.svg | BK-5Br-NM-AMT (5-bromo-α,N-dimethyl-β-ketotryptamine)[87][90][91] | 1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one  |

### List of substituted β-ketotryptamines

A number of β-ketotryptamines (beta-ketotryptamines) are known.[82][84][87] These compounds are α-alkyl-β-ketotryptamines and are analogous to the cathinones (β-ketoamphetamines) of the related phenethylamine family. Known β-ketotryptamines include BK-NM-AMT, BK-5F-NM-AMT, BK-5Cl-NM-AMT, and BK-5Br-NM-AMT.[82][84][87] They act as monoamine releasing agents.[82][84][87]

### Cyclized tryptamines

Examples of cyclized tryptamines include:

* β-Carbolines such as harmala alkaloids like harmaline
* Ibogalogs (hexahydroazepinoindoles) such as ibogainalog, tabernanthalog, PNU-22394, and PHA-57378
* Iboga alkaloids like ibogaine, noribogaine, ibogamine, and tabernanthine
* Ergolines and lysergamides such as lysergic acid diethylamide (LSD) and ergot alkaloids like ergine (lysergic acid amide; LSA)
* Partial ergolines and lysergamides like RU-27849, FHATHBIN, NDTDI, and CT-5252
* Mitragyna alkaloids such as mitragynine
* Yohimbans such as Rauvolfia and Corynanthe alkaloids like yohimbine and rauwolscine
* Pyrrolidinylethylindoles like pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, and L-760790
* Pyrrolidinylmethylindoles like MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-135807, eletriptan, and MSP-2020
* Imidazolylindoles like AGH-107, AGH-192, and AH-494
* Piperidinylethylindoles like pip-T, 5-MeO-pip-T, and indoramin
* Morpholinylethylindoles like mor-T and 5-MeO-mor-T
* Tetrahydropyridinylindoles like RS134-49 (4-Me-THPI), RU-28253 (5-MeO-THPI), and NEtPhOH-THPI
* Pertines (phenylpiperazinylethylindoles) like alpertine, milipertine, oxypertine, and solypertine
* Tetrahydrocarbazolamines like ciclindole, flucindole, frovatriptan, LY-344864, and ramatroban
* Tetrahydropyrroloquinolines like bufothionine, O-methylnordehydrobufotenine, and dehydrobufotenine
* Others like 5-MeO-IsoqT, barettin, cyclic 3-hydroxymelatonin, metralindole, and Z5247692566

Other closely related cyclized tryptamine-like compounds include the following:

* Piperidinylindoles like SN-22, BRL-54443, naratriptan, LY-334370, and sertindole
* Tetrahydropyridinylindoles like RU-24969, EMD-386088, and LY-367,265
* Tetrahydropyridinylindazoles like VU6067416
* Tetrahydropyridinylpyrrolopyridines like (R)-69, (R)-70, CP-93129, and CP-94253
* Pyridopyrroloquinoxalines (tetracyclic γ-carbolines) like lumateperone, IHCH-7113, IHCH-7086, and ITI-1549

## Related compounds

A number of related compounds are known, with a similar structure but having the indole core flipped (isotryptamines) and/or replaced with related cores such as indene, indoline, indazole, indolizine, benzothiophene, or benzofuran. Like tryptamines, these related compounds are primarily active as agonists at the 5-HT2 family of serotonin receptors, with applications in the treatment of glaucoma, cluster headaches, or as anorectics.

Template:Sticky

Structure  | Name  | Chemical name  | CAS #

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File:C-DMT.svg | C-DMT (1-carba-DMT)  | 2-(3H-inden-1-yl)-N,N-dimethylethanamine  |
File:O-DMT chemical structure.svg | O-DMT (1-oxa-DMT, DMBF)  | 2-(1-benzofuran-3-yl)-N,N-dimethylethanamine  |
File:MiPBF.svg | MiPBF (1-oxa-MiPT)  | N-[2-(1-benzofuran-3-yl)ethyl]-N-methylpropan-2-amine  |
File:Dimemebfe structure.svg | Dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT)  | 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine  | 140853-58-3
File:5-MeO-DiBF structure.svg | 5-MeO-DiBF (1-oxa-5-MeO-DiPT)  | N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine  |
File:3-APB.svg | 3-APB (1-oxa-AMT)  | 3-(2-aminopropyl)benzofuran  | 105909-13-5
File:Mebfap 2D.svg | Mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT)  | 3-(2-aminopropyl)-5-methoxybenzofuran  | 140853-59-4
File:S-DMT.svg | S-DMT (1-thia-DMT)  | 2-(1-benzothiophen-3-yl)-N,N-dimethylethanamine  | 10275-64-6
File:3-APBT.svg | 3-APBT (SKF-6678; 1-thia-AMT)  | 1-(1-benzothiophen-3-yl)propan-2-amine  | 1201-27-0
File:Isotryptamine.svg | Isotryptamine (isoT)  | 2-indol-1-ylethanamine  | 13708-58-2
File:IsoAMT chemical structure.svg | isoAMT | 1-indol-1-ylpropan-2-amine  | 1227465-67-9
File:(S)-5,6-Difluoro-isoAMT.svg | (S)-5,6-Difluoro-isoAMT [92] | (S)-1-(5,6-difluoroindol-1-yl)propan-2-amine  |
| Ro60-0175 ((S)-5-F-6-Cl-isoAMT)  | (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine  | 169675-09-6
File:IsoDMT.svg | isoDMT | 2-indol-1-yl-N,N-dimethylethanamine  | 87482-09-5
File:5-MeO-isoDMT.svg | 5-MeO-isoDMT | 2-(5-methoxyindol-1-yl)-N,N-dimethylethanamine  | 244122-80-3
File:6-MeO-isoDMT.svg | 6-MeO-isoDMT | 2-(6-methoxyindol-1-yl)-N,N-dimethylethanamine  | 87482-11-9
| Zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-Me-isoDMT)  | (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine  | 2481740-94-5
File:TACT908.svg | 2ZEDMA  | 2-indolizin-1-yl-N,N-dimethylethanamine  |
File:1ZP2MA.svg | 1ZP2MA | 1-indolizin-1-yl-N-methylpropan-2-amine  |
File:1Z2MAP1O chemical structure.svg | 1Z2MAP1O | 1-indolizin-3-yl-2-(methylamino)propan-1-one  | 2110204-31-2
File:Example16 structure.png | Example 16 [93][94] | 1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine  |
| Example 1 [95] | 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine  |
| VER-3323 | (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine  | 259857-99-3
| AL-34662 (indazole-5-HO-AMT)  | 1-((S)-2-Aminopropyl)-1H-indazol-6-ol  | 210580-75-9
File:O-Methyl-AL-34662.svg | O-Methyl-AL-34662 (indazole-5-MeO-AMT)  | 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole  | 210580-60-2
File:7-Methyl-AL-34662.svg | 7-Methyl-AL-34662  | 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol  | 874668-67-4
File:7-Chloro-AL-34662.svg | 7-Chloro-AL-34662  | 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol  | 874881-86-4
File:AL-38022A structure.svg | AL-38022A | (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine  | 478132-11-5
| Example 9 [96] | (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine  | 478132-12-6
| Example 3 [97] | (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine  | 890087-75-9
| Example 1 [98] | (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine  | 1373917-69-1
| YM-348 | (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine  | 372163-84-3
| 2-Desethyl-YM-348 [99] | (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine  | 748116-94-1
| I-32 [100] | 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol  |
| 2-Azapsilocin (Psilocin indazole analogue, P-6)[101] | 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol  |
File:4-Aza-5-MeO-DPT structure.png | 4-Aza-5-MeO-DPT (P-11)  | N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine  |
| 5-Aza-4-MeO-DiPT (P-36)  | N-[2-(4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine  |
| 7-Aza-5-MeO-DiPT (P-19)  | N-[2-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine  |
File:RS134-49.svg | RS134-49 (4-Me-THPI)  | 4-methyl-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole  | 2945139-94-4
File:RU-28253.svg | RU-28253 (5-MeO-THPI)  | 5-methoxy-3-(1,2,3,6-tetrahydropyridin-5-yl)-1H-indole  | ?
File:NEtPhOH-THPI.svg | NEtPhOH-THPI (compound 24c)  | 3-(1-(2-hydroxyphenylethyl)-1,2,3,6-tetrahydropyridin-5-yl)-1H-indole  | ?
File:VU6067416 2D.svg | VU6067416[102] | 3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole  | 3027515-24-5
File:(R)-69.svg | (R)-69 | 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine  | 2765652-48-8
File:R-70.svg | (R)-70  | 3-[(3R)-1,3-dimethyl-3,6-dihydro-2H-pyridin-5-yl]-1H-pyrrolo[2,3-b]pyridine  | ?
File:SN-22 structure.svg | SN-22 | 3-(1-methylpiperidin-4-yl)-1H-indole  | 17403-07-5
File:RU-24969.svg | RU-24,969 | 5-methoxy-3-(1,2,5,6-tetrahydro-4-pyridinyl)-1H-indole  | 107008-28-6
| EMD-386088 | 5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole  | 54635-62-0
File:T-70 structure.svg | T-70[103] | N,N-dimethyl-2-(6H-thieno[2,3-b]pyrrol-4-yl)ethan-1-amine  | ?
File:T-72 structure.svg | T-72[104] | N,N-dimethyl-2-(4H-thieno[3,2-b]pyrrol-6-yl)ethan-1-amine  | ?
File:Gramine.svg | Gramine | 1-(1H-indol-3-yl)-N,N-dimethylmethanamine  | 87-52-5
File:Homotryptamine structure.svg | Homotryptamine  | 3-(1H-indol-3-yl)propan-1-amine  | 6245-89-2
File:Dimethylhomotryptamine structure.svg | Dimethylhomotryptamine (DMHT)  | 3-(1H-indol-3-yl)-N,N-dimethylpropan-1-amine  | 13117-35-6
File:Benzydamine tryptamine orientation.svg | Benzydamine | 3-(1-benzyl-1H-indazol-3-yloxy)-N,N-dimethylpropan-1-amine  | 642-72-8
File:Indalpine structure.svg | Indalpine | 3-(2-piperidin-4-ylethyl)-1H-indole  | 63758-79-2
File:Methylindolylethylpyridine.svg | Methylindolylethylpyridine (IN-399)  | 1-methyl-3-(2-pyridin-4-ylethyl)indole  | 16571-53-2
File:Benzindopyrine structure.svg | Benzindopyrine (pyrbenzindole; IN-461)  | 1-benzyl-3-(2-pyridin-4-ylethyl)indole  | 16571-59-8

## Overview table

Template:Simple tryptamines and their common derivatives

## See also

* Arylalkylamine
* Substituted β-carboline
* Ibogalog
* Iboga alkaloid
* Lysergamide
* TiHKAL
* List of miscellaneous 5-HT2A receptor agonists
* Substituted isotryptamine
* Indazolylethylamine
* Indolizinylethylamine
* Tetrahydropyridinylpyrrolopyridine
* Substituted 2-aminoindane
* Substituted amphetamine
* Substituted benzofuran
* Substituted cathinone
* Substituted methylenedioxyphenethylamine
* Substituted phenethylamine
* 2C, DOx, 25-NB

## References

1. ↑ Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable" (in en). https://phys.org/news/2022-12-psychoactive-compounds-mushrooms-extremely-variable.html.
2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.
3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr 146: 74–91. 1994. PMID 8742795. https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79.
4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6.
5. ↑ "Chemistry of Psychotomimetics". Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. 55 / 3. Berlin: Springer Berlin Heidelberg. 1982. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916. https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1.
6. ↑ Alexander T. Shulgin (1980). "Hallucinogens". Burger's Medicinal Chemistry. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5.
7. ↑ 7.0 7.1 7.2 7.3 "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol 21 (10): 926–931. October 2018. doi:10.1093/ijnp/pyy047. PMID 29850881.
8. ↑ 8.0 8.1 8.2 8.3 Halberstadt, Adam L.; Chatha, Muhammad; Klein, Adam K.; Wallach, Jason; Brandt, Simon D. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced Seminars in Neuroendocrinology/Serotonergic Psychedelics 20/Halberstadt 20 Neuropharm potency of hallucinogens head-twitch.pdf. "Table 4 Human potency data for selected hallucinogens. [...]".
9. ↑ 9.0 9.1 9.2 9.3 Ballentine, Galen; Friedman, Samuel Freesun; Bzdok, Danilo (March 2022). "Trips and neurotransmitters: Discovering principled patterns across 6850 hallucinogenic experiences". Sci Adv 8 (11). doi:10.1126/sciadv.abl6989. PMID 35294242. Bibcode: 2022SciA....8L6989B.
10. ↑ 10.0 10.1 "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl) 239 (6): 1783–1796. June 2022. doi:10.1007/s00213-022-06142-4. PMID 35487983.
11. ↑ 11.0 11.1 11.2 11.3 11.4 11.5 "Biochemistry and pharmacology of tryptamines and beta-carbolines. A minireview". J Psychoactive Drugs 16 (4): 347–358. 1984. doi:10.1080/02791072.1984.10472305. PMID 6394730. https://bitnest.netfirms.com/external/10.1080/02791072.1984.10472305.
12. ↑ Cite error: Invalid `<ref>` tag; no text was provided for refs named `LiechtiHolze2022`
13. ↑ 13.0 13.1 Cite error: Invalid `<ref>` tag; no text was provided for refs named `HolzeSinghLiechti2024`
14. ↑ "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences 21 (23): 9279. December 2020. doi:10.3390/ijms21239279. PMID 33291798. "4-OH-DPT is the 4-hydroxylated DPT derivative first synthesized by Shulgin et al. [82]. 4-OH-DPT is a light beige or white powder [54] that acts as a 5-HT2A partial agonist. 4-OH-DPT also shares structural similarity with psilocin [83]. Effects are dose dependent, with onset at 15–45 min and duration of 5–8 h. According to user reports, synthetic 4-OH-DPT produces visual effects and hallucinatory states [84].".
15. ↑ "Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of Subcutaneous RE104: A Double-Blind, Randomized, Single Ascending Dose Placebo-Controlled Study". J Clin Psychopharmacol 45 (5): 441–453. 2025. doi:10.1097/JCP.0000000000002047. PMID 40685873.
16. ↑ "4-AcO-DMT (Ацетилпсилоцин)" (in ru). https://aipsin.com/newsubstance/671/.
17. ↑ "Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine". Journal of Psychoactive Drugs 33 (3): 273–281. 2001. doi:10.1080/02791072.2001.10400574. PMID 11718320.
18. ↑ "Shamanic-Snuff Psychonautica: Pharmañopo: Bufotenine—Psychonautics". Shamanic Snuffs or Entheogenic Errhines. Entheobotanica. 2001. pp. 99–116 (105–112, 114–115). ISBN 978-1-888755-02-2. OCLC 56061312. https://archive.org/details/vdocuments.mx_unknown-55b347d139b58/page/n51/mode/1up. Retrieved 24 January 2025.
19. ↑ "A New One-Hour Talk On 5-MeO-DMT". Patreon. 1 December 2022. https://www.patreon.com/posts/new-one-hour-on-75373519. "[Morris:] Bufotenine is a drug that I have tried. I've tried isolated pure bufotenine and it is a psychedelic that is both pharmacologically and experientially and chemically intermediate between DMT and 5-MeO-DMT. So it has a longer duration than actually both 5-MeO-DMT and DMT. It's yet less visual than DMT but more visual than 5-MeO-DMT, so it's kind of like in-between the two. It's also very nauseating, which is the main reason that people seem not to enjoy it very much. But it is a classical psychedelic drug that produces visionary effects. And Jonathan Ott actually liked the effect of it quite a bit."
20. ↑ Hamilton Morris (1 September 2021). "PODCAST 28: A talk with Jonathan Ott". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 49:20–50:36. Retrieved 20 January 2025. "[Morris:] I've used [bufotenine] a couple times, once at 50 milligrams of the freebase snorted. [...] I found it to be extremely nauseating. I found it to be qualitatively intermediate between 5-MeO-DMT and DMT in that it was more visual than my experiences with 5-MeO-DMT but less visual than my typical experiences with DMT. It had a longer duration than 5-MeO-DMT and maybe even a longer duration than DMT as well. It was about an hour. Although I don't have all that much experience snorting DMT freebase."
21. ↑ Cite error: Invalid `<ref>` tag; no text was provided for refs named `Ott1999`
22. ↑ "5-MeO-MsBT (5-methoxy-N-methyl-N-secbutyltryptamine)" (in ru). https://aipsin.com/newsubstance/987/.
23. ↑ "Unusual Analogues: Drugs Used by Gordon Todd Skinner". This Land Press. http://thislandpress.com/2013/07/25/unusual-analogues-drugs-used-by-gordon-todd-skinner/.
24. ↑ Hamilton Morris (29 April 2025). "POD 126: The Return of Psychedelic Selenium with Dr. Josh Hartsel". The Hamilton Morris Podcast (Podcast). Patreon. Event occurs at 1:33:53–1:35:50. "[...] [Hartsel:] The α,N,N-Dimethyl[tryptamine]. [Morris:] Oh yeah, I've made it and tried it actually. [Hartsel:] Oh you did? [Morris:] Yeah, yeah. [Hartsel:] Oh, well what did it do? [Morris:] It is active, it's an active psychedelic. It's reduced potency. I never got it to a dose where it produced particularly interesting effects. I can look up the exact dose. I think it was like... the only thing I remember is that I felt like it was making me sneeze a lot. But it was very pleasant. Nothing bad happened. But the dose just wasn't high enough. I think I took maybe 40 mg. So it was much less potent than AMT orally. The other issue of course is that it could be a prodrug of N-methyl-AMT, which is active, or AMT itself maybe. [...]"
25. ↑ "Sea DMT: God Molecule or Barnacle Repellent?". Vice. 26 March 2013. https://www.vice.com/en/article/sea-dmt-000481-v20n3/.
26. ↑ Marek GJ, Makai-Bölöni S, Umbricht D, Christian EP, Winters J, Dvorak D, Raines S, Hughes ZA, Austin EW, Klein AK, Leong W, Krol FJ, Graaf AJV, Juachon MJ, Otto ME, Borghans LGJM, Jacobs G, Kruegel AC, Sporn J. A novel psychedelic 5-HT2A receptor agonist GM-2505: The pharmacokinetic, safety, and pharmacodynamic profile from a randomized trial healthy volunteer. J Psychopharmacol. 2025 Oct 16:2698811251378512. doi:10.1177/02698811251378512 PMID 41099491
27. ↑ Szara, Stephen; Hearst, Eliot (1962). "The 6-Hydroxylation of Tryptamines Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences 96 (1): 134–141. doi:10.1111/j.1749-6632.1962.tb50108.x. ISSN 0077-8923. Bibcode: 1962NYASA..96..134S. "This correlation between metabolic transformation rates and psychological effect is suggestive. It strengthens our notion that metabolically formed 6-HDET most likely plays a role in producing the psychological effects. A more stringent test would be to give the metabolite directly to the same subjects, as was done in the animal experiments. Unfortunately we did not have enough synthetic 6-HDET to do extensive human studies, so the senior author tried it out himself. Both 1 and 2 mg. of 6-HDET had no noticeable effect. At 5 mg. there was only a very faint short-lasting perceptual disturbance. Then, on the fourth attempt, 10 mg. of 6-HDET was administered. No obvious effect on behavior occurred in the first hour, but then typical psychotomimetic disturbances began to appear. For the next 2 or 3 hours hallucinogenic effects were observed that were very similar to the effect of 60 mg. of DET. These experiments lead us to believe that 6-HDET in man is 5 to 6 times more active psychotropically than DET, but more extended studies will be necessary to establish the exact form of the relationship.".
28. ↑ "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics". Neuron 113 (19): 3129–3142.e9. July 2025. doi:10.1016/j.neuron.2025.06.012. PMID 40683247. https://www.cell.com/cms/10.1016/j.neuron.2025.06.012/attachment/7d8365fe-51f3-4a28-bf40-9999bec837f6/mmc11.pdf.
29. ↑ "Psychedelics and the human receptorome". PLOS ONE 5 (2). February 2010. doi:10.1371/journal.pone.0009019. PMID 20126400. Bibcode: 2010PLoSO...5.9019R.
30. ↑ 30.0 30.1 "Some new psychoactive substances: precursor chemicals and synthesis-driven end-products". Drug Test Anal 3 (7–8): 404–416. 2011. doi:10.1002/dta.315. PMID 21755608.
31. ↑ 31.0 31.1 "Recreational drug discovery: natural products as lead structures for the synthesis of smart drugs". Nat Prod Rep 31 (7): 880–904. July 2014. doi:10.1039/c4np00010b. PMID 24823967.
32. ↑ Shaba, Reham (24 September 2020). "Development of an improved psilocybin synthesis". https://www.diva-portal.org/smash/record.jsf?pid=diva2:1470170&dswid=-3583.
33. ↑ "We Licked the Toads so You Don't Have to: A Comprehensive Analysis of the Chemical Syntheses of the Classical Psychedelics Bufotenin(e) and 5-Methoxy-N,N-Dimethyltryptamine". ChemMedChem 21 (4). February 2026. doi:10.1002/cmdc.202500525. PMID 41765690.
34. ↑ "1,1-dideuterio-2-(1H-indol-3-yl)ethanamine". https://pubchem.ncbi.nlm.nih.gov/compound/10654563.
35. ↑ "2,2-dideuterio-2-(1H-indol-3-yl)ethanamine". https://pubchem.ncbi.nlm.nih.gov/compound/12238690.
36. ↑ "5-METHOXYTRYPTAMINE-alpha,alpha,beta,beta-D4". https://pubchem.ncbi.nlm.nih.gov/compound/12273662.
37. ↑ Kozikowski A, et al. 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators. Patent WO 2021/179091
38. ↑ "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE 14 (1). 2019. doi:10.1371/journal.pone.0209804. PMID 30629611. Bibcode: 2019PLoSO..1409804T.
39. ↑ Jensen N (2004). Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens (PhD thesis). Georg-August-Universität zu Göttingen.
40. ↑ 40.0 40.1 Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, et al. (December 2023). "AlphaFold2 structures template ligand discovery". bioRxiv 10.1101/2023.12.20.572662.
41. ↑ 41.0 41.1 "Towards "unmakable" psychedelics: SAR exploration of psilocin analogs obtained by a HATU-mediated amide coupling strategy". European Journal of Medicinal Chemistry Reports 15. 2025. doi:10.1016/j.ejmcr.2025.100278.
42. ↑ "3-[2-(2-azabicyclo[2.2.2octan-2-yl)ethyl]-1H-indole"]. https://pubchem.ncbi.nlm.nih.gov/compound/53634044.
43. ↑ "N,N-diethyl-3-[ethyl-[2-(1H-indol-3-yl)ethylamino]propanamide"]. https://pubchem.ncbi.nlm.nih.gov/compound/208162.
44. ↑ "Analogues of Psilocin and Lysergic acid diethylamide I. Chloro, Nitro, and Amino Derivatives of 3-Substituted Indoles.". Canadian Journal of Chemistry 41 (10): 2585–2590. October 1963. doi:10.1139/v63-378. Bibcode: 1963CaJCh..41.2585M.
45. ↑ "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science 4 (2): 533–542. April 2021. doi:10.1021/acsptsci.0c00176. PMID 33860183.
46. ↑ "Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug". Acta Crystallographica Section E 77 (Pt 2): 101–106. February 2021. doi:10.1107/S2056989021000116. PMID 33614134. Bibcode: 2021AcCrE..77..101P.
47. ↑ Banister S, Jorgensen W, Jinlong T, "Compounds", WO patent 2023115167, published 29 June 2023
48. ↑ Kozikowski A, Shaprio G, Tueckmantel W, McCorvy J, "3-(2-(Aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-HT2 receptor modulators", WO patent 2021179091, published 16 September 2021, assigned to Bright Minds Biosciences Inc.and The Medical College Of Wisconsin Inc.
49. ↑ Stamets PE, "Tryptamine Compositions for Enhancing Neurite Outgrowth.", WO patent 2021101926, published 2021-05-27, assigned to Stamets Paul Edward.
50. ↑ Kruegel AC, Sporn J, "Specific Tryptamines for use in the Treatment of Mood Disorders.", WO patent 2021168082, published 26 August 2021
51. ↑ "N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist". Journal of Medicinal Chemistry 42 (3): 526–31. February 1999. doi:10.1021/jm9805945. PMID 9986723.
52. ↑ Kruegel AC, "Novel Tryptamines and Methods of Treating Mood Disorders", WO patent 2022235927, published 10 November 2022, assigned to Gilgamesh Pharmaceuticals, Inc.
53. ↑ "The synthesis of nitro-and aminoindoles analogous to serotonin.". Journal of the American Chemical Society 75 (8): 1877–1881. April 1953. doi:10.1021/ja01104a029. Bibcode: 1953JAChS..75.1877S.
54. ↑ "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior 72 (1–2): 29–37. May 2002. doi:10.1016/s0091-3057(01)00720-1. PMID 11900766.
55. ↑ "N,N-dimethyl-2-[6-(trifluoromethoxy)-1H-indol-3-ylethanamine"]. https://pubchem.ncbi.nlm.nih.gov/compound/172291242.
56. ↑ Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery, 10 March 2023, doi:10.21203/rs.3.rs-2667175/v1, https://www.researchsquare.com/article/rs-2667175/latest.pdf, retrieved 17 March 2025
57. ↑ "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". The Journal of Biological Chemistry 299 (10). October 2023. doi:10.1016/j.jbc.2023.105231. PMID 37690691.
58. ↑ "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry 23 (11): 1222–6. November 1980. doi:10.1021/jm00185a014. PMID 6779006.
59. ↑ Kozikowski A, et al. 3-(2-(aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-ht2 receptor modulators. Patent WO 2021/179091
60. ↑ "1-[3-[2-(Dimethylamino)ethyl-1H-indol-1-yl]ethanone"]. https://pubchem.ncbi.nlm.nih.gov/compound/85809048.
61. ↑ 61.0 61.1 Kargbo, Robert B. (13 April 2023). "Orally Active Forms of DMT, 5-MeO-DMT, and Long-Acting MDMA for the Treatment of Neuropsychiatric Disorders". ACS Medicinal Chemistry Letters 14 (4): 367–368. doi:10.1021/acsmedchemlett.3c00077. ISSN 1948-5875. PMID 37077395. PMC 10108390. https://pubs.acs.org/doi/10.1021/acsmedchemlett.3c00077.
62. ↑ 62.0 62.1 "N,n-dimethyltryptamine and related psychedlics and uses thereof". 7 July 2022. https://patents.google.com/patent/WO2023283364.
63. ↑ "1-[3-[2-(Dimethylamino)ethyl-5-methoxy-1H-indol-1-yl]ethanone"]. https://pubchem.ncbi.nlm.nih.gov/compound/85809049.
64. ↑ "Tert-butyl 3-[2-(dimethylamino)ethyl-5-methoxyindole-1-carboxylate"]. https://pubchem.ncbi.nlm.nih.gov/compound/166467630.
65. ↑ 65.0 65.1 "Heterocyclic compounds and methods of preparation thereof". 25 May 2022. https://patents.google.com/patent/WO2022246554A1/en.
66. ↑ "3-[2-(Dimethylamino)ethyl-7-methyl-1H-indol-4-ol"]. https://pubchem.ncbi.nlm.nih.gov/compound/166138173.
67. ↑ "[3-[2-(dimethylamino)ethyl-7-methyl-1H-indol-4-yl] dihydrogen phosphate"]. https://pubchem.ncbi.nlm.nih.gov/compound/162744827.
68. ↑ Sabnis RW. Novel Heterocyclic Compounds as 5‑HT2C Agonists for Treating Depression, Drug Addiction, Alcoholism, PTSD and Neuropathic Pain. ACS Med Chem Lett. 2025 Jul 9;16(8):1488-1489. doi:10.1021/acsmedchemlett.5c00400 PMID 40832508
69. ↑ Banister S, Jorgensen W, Jinlong T, "Compounds", WO patent 2023115166, published 29 June 2023
70. ↑ 70.0 70.1 Principles of Addiction Medicine. Lippincott Williams & Wilkins. 2009. pp. 216–218. ISBN 978-0-7817-7477-2. https://books.google.com/books?id=j6GGBud8DXcC&pg=PT245.
71. ↑ 71.0 71.1 71.2 Hallucinogens: A Forensic Drug Handbook. Academic Press. 2003. pp. 102–. ISBN 978-0-12-433951-4. https://books.google.com/books?id=l1DrqgobbcwC&pg=PA102.
72. ↑ 72.0 72.1 72.2 72.3 72.4 Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. 24 January 2012. pp. 641–. ISBN 978-1-60913-345-0. https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA641.
73. ↑ "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology 559 (2–3): 132–7. March 2007. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
74. ↑ "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters 24 (19): 4754–4758. October 2014. doi:10.1016/j.bmcl.2014.07.062. PMID 25193229.
75. ↑ "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin 30 (12): 2328–33. December 2007. doi:10.1248/bpb.30.2328. PMID 18057721.
76. ↑ "Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insluin secretion". Diabetologia 11 (6): 487–94. December 1975. doi:10.1007/bf01222097. PMID 1107123.
77. ↑ "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology 200 (1): 187–90. July 1991. doi:10.1016/0014-2999(91)90686-K. PMID 1722753.
78. ↑ "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorganic & Medicinal Chemistry Letters 12 (2): 155–8. January 2002. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343.
79. ↑ Macor JE, Wythes MJ, "Indole derivatives", US patent 5607951, issued 4 March 1997, assigned to Pfizer, Inc.
80. ↑ Wallach J, Dybek M, "Fluorinated Tryptamine Compounds, Analogues Thereof, and Methods Using Same.", WO patent 2022256554, published 8 December 2022, assigned to University Of The Sciences.
81. ↑ "AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery?". Nature News 626 (7997): 14–15. 18 January 2024. doi:10.1038/d41586-024-00130-8. PMID 38238624. Bibcode: 2024Natur.626...14C.
82. ↑ 82.0 82.1 82.2 82.3 "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology (Berl) 236 (3): 915–924. March 2019. doi:10.1007/s00213-018-5063-9. PMID 30341459.
83. ↑ "1-(1H-indol-3-yl)-2-(methylamino)propan-1-one". https://pubchem.ncbi.nlm.nih.gov/compound/82282492.
84. ↑ 84.0 84.1 84.2 84.3 84.4 & Sean Dalziel"Specialized combinations for mental disorders or mental enhancement" US patent 20240335414, published 10 October 2024
85. ↑ "1-(5-fluoro-1H-indol-3-yl)-2-(methylamino)propan-1-one". https://pubchem.ncbi.nlm.nih.gov/compound/162765676.
86. ↑ "β-Oxo-5-fluoro-α-methyl-NMT". 10 November 2024. https://isomerdesign.com/pihkal/explore/12714.
87. ↑ 87.0 87.1 87.2 87.3 87.4 87.5 Matthew Baggott, "Advantageous tryptamine compositions for mental disorders or enhancement", WO patent 2022061242, published 2023 March 24, assigned to Tactogen
88. ↑ "1-(5-chloro-1H-indol-3-yl)-2-(methylamino)propan-1-one". https://pubchem.ncbi.nlm.nih.gov/compound/162765502.
89. ↑ "β-Oxo-5-chloro-α-methyl-NMT". 10 November 2024. https://isomerdesign.com/pihkal/explore/12715.
90. ↑ "1-(5-bromo-1H-indol-3-yl)-2-(methylamino)propan-1-one". https://pubchem.ncbi.nlm.nih.gov/compound/162765532.
91. ↑ "β-Oxo-5-bromo-α-methyl-NMT". 10 November 2024. https://isomerdesign.com/pihkal/explore/12725.
92. ↑ "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorg Med Chem Lett 12 (2): 155–158. January 2002. doi:10.1016/s0960-894x(01)00713-2. PMID 11755343. "Detailed re-examination of a compound previously reported to display 100-fold 5-HT2C selectivity [i.e., S(+)-5,6-difluoro-α-methylisotryptamine] revealed that its selectivity versus 5-HT2A receptors was, at best, only 10-fold.".
93. ↑ Kargbo RB (Jan 2024). "Neuropharmacological Advances: Harnessing 5-HT2A Receptor Modulators and Psychoplastogens". ACS Med Chem Lett 15 (2): 171–173. doi:10.1021/acsmedchemlett.4c00003. PMID 38352827.
94. ↑ Powell NA, Chytil M. Imidazopyridine psychoplastogens and uses thereof. WO 2023/114844
95. ↑ Chen HH, May JA, "Pyranoindoles for treating glaucoma", US patent granted 7012090, published 17 March 2000, issued 14 March 2006, assigned to Alcon, Inc.
96. ↑ Chen HH, May JA, Severns BS, "Pyranoindazoles and their use for the treatment of glaucoma", US patent granted 6881749, published 3 June 2004, issued 19 April 2005, assigned to Alcon, Inc.
97. ↑ Chen HH, May JA, "Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma", US patent granted 7425572, published 8 June 2006, issued 16 September 2008, assigned to Alcon, Inc.
98. ↑ "Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma" US patent granted 7268131, published 15 December 2005, issued 11 September 2007, assigned to Alcon, Inc.
99. ↑ "Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists". Bioorganic & Medicinal Chemistry 16 (4): 1966–82. February 2008. doi:10.1016/j.bmc.2007.10.100. PMID 18035544.
100. ↑ Slassi A, Araujo J, Higgins G, "3-Cyclic Amine-Indole Derivatives as Serotonergic Agents for the Treatment of CNS Disorders.", WO patent 2022120475, published 16 June 2022
101. ↑ Banister S, Jorgensen W, Jinlong T, "Compounds", WO patent 2023115165, published 29 June 2023
102. ↑ Jayakodiarachchi N (2024). "Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists". ACS Med. Chem. Lett. 15 (2): 302–309. doi:10.1021/acsmedchemlett.3c00566. PMID 38352850.
103. ↑ "T-70 - PiHKAL·info". 12 June 2025. https://isomerdesign.com/pihkal/explore/5068.
104. ↑ "T-72 - PiHKAL·info". 12 June 2025. https://isomerdesign.com/pihkal/explore/5067.

## External links

* Psychedelic Tryptamines - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual Psychedelic Tryptamines)

* v
* t
* e

Tryptamines

* 1-Methylpsilocin
* 2-Methyl-5-HT
* 4,5-DHP-DMT
* 4,5-MDO-DMT
* 4,5-MDO-DiPT
* 4-AcO-DALT
* 4-AcO-DET
* 4-AcO-DMT
* 4-AcO-DiPT
* 4-AcO-NMT
* 4-AcO-MET
* 4-AcO-DPT
* 4-AcO-MiPT
* 4-HO-DALT
* 4-HO-DET
* 4-HO-DiPT
* 4-HO-DPT
* 4-HO-DSBT
* 4-HO-EPT
* 4-HO-MALT
* 4-HO-MET
* 4-HO-McPT
* 4-HO-McPeT
* 4-HO-MiPT
* 4-HO-MPT
* 4-HO-NMT
* 4-HO-αMT
* 4-Me-αET
* 4-Me-αMT
* 4-MeO-DiPT
* 4-MeO-DMT
* 5-BT
* 5-Bromo-DMT
* 5-CT
* 5-Chloro-αMT
* 5-Ethoxy-αMT
* 5-Fluoro-αMT
* 5-HO-αMT
* 5-HO-DiPT
* 5-HTP
* 5-Ethoxy-DMT
* 5-Ethyl-DMT
* 5-Fluoro-DMT
* 5-Methyl-DMT
* 5-Methoxytryptamine
* 5-MeO-7,N,N-TMT
* 5-Methyl-αET
* 5-MeO-αET
* 5-MeO-αMT
* 5-MeO-DALT
* 5-MeO-DET
* 5-MeO-DiPT
* 5-MeO-DMT
* 5-MeO-DPT
* 5-MeO-EiPT
* 5-MeO-EPT
* 5-MeO-MALT
* 5-MeO-MiPT
* 5-MeO-NBpBrT
* 5,7-Dihydroxytryptamine
* 5-(Nonyloxy)tryptamine
* 6-Fluoro-αMT
* 6-Hydroxymelatonin
* 7-Methyl-αET
* 7-Methyl-DMT
* Acetryptine
* Aeruginascin
* αET
* AL-37350A
* αMT
* Baeocystin
* BNC-210
* Bufotenidine
* Bufotenin (5-HO-DMT)
* BW-723C86
* Convolutindole A
* DALT
* Desformylflustrabromine
* DET
* DiPT
* DMT
* DPT
* E-6801
* E-6837
* Ethocybin
* EiPT
* EMDT
* EPT
* FGIN-127
* FGIN-143
* HIOC
* Ibogaine
* Idalopirdine
* Indorenate
* Iprocin
* Lespedamine
* Luzindole
* MET
* MiPT
* MPT
* Miprocin
* Melatonin
* MS-245
* NAS
* N-Feruloylserotonin
* NMT
* Norbaeocystin
* Normelatonin
* O-4310
* Oxypertine
* Plakohypaphorine
* PiPT
* Psilocin (4-HO-DMT)
* Psilocybin (4-PO-DMT)
* Rizatriptan
* Serotonin
* ST-1936
* Sumatriptan
* Tryptamine
* Tryptophan
* Yohimbine
* Yuremamine
* Zolmitriptan

* v
* t
* e

Psychedelics

Tryptamines|

| No ring subs.|

* CYB004 (deuDMT)
* DALT
* DBT
* DET (T-9)
* DiPT
* DMT
* DMT-d4 (D4DMT)
* DPT
* EiPT
* EPT
* iPALT (ALiPT)
* MALT
* McPT
* MET
* MiPT
* MPT
* NMT
* PALT
* PiPT
* SPL028 (D2-DMT)
* Tryptamine (T)

|

4-Hydroxytryptamines|

* 4-HO-DALT (daltocin)
* 4-HO-DBT
* 4-HO-DET (ethocin; CZ-74)
* 4-HO-DiPT (iprocin)
* 4-HO-DPT (deprocin)
* 4-HO-EPT (eprocin)
* 4-HO-MALT (maltocin)
* 4-HO-McPT
* 4-HO-MET (metocin)
* 4-HO-MiPT (miprocin)
* 4-HO-MPT (meprocin)
* 4-HO-NALT
* 4-HO-NBnT
* 4-HO-NET
* 4-HO-NiPT
* 4-HO-NPT
* 4-HO-TMT
* 4-HO-5-MeO-DMT
* 4-HO-T (4-HT)
* 4-MeO-DMT
* CYB003 (deupsilocin)
* Psilocin (4-HO-DMT; CX-59)

* 4-Phosphoryloxytryptamines: Aeruginascin (4-PO-TMT)
* Baeocystin (4-PO-NMT)
* Ethocybin (4-PO-DET; CEY-19)
* Norbaeocystin (4-PO-T)
* Psilocybin (4-PO-DMT; CY-39)

* 4-Acyloxytryptamines: 4-AcO-DALT (daltacetin)
* 4-AcO-DET (ethacetin)
* 4-AcO-DiPT (ipracetin)
* 4-AcO-DMT (psilacetin)
* 4-AcO-DPT (depracetin)
* 4-AcO-EiPT (ethipracetin)
* 4-AcO-EPT
* 4-AcO-MALT
* 4-AcO-McPT
* 4-AcO-MET (metacetin)
* 4-AcO-MiPT (mipracetin)
* 4-AcO-MPT
* 4-GO-DMT (RE-109)
* 4-PrO-DiPT
* 4-PrO-DMT
* 4-PrO-MET
* Luvesilocin (4-GO-DiPT; RE-104, FT-104)

5-Hydroxytryptamines|

* 5-HO-MET
* Bufotenin (5-HO-DMT)
* Serotonin (5-HT; 5-HO-T)

* 5-Acyloxytryptamines: O-Acetylbufotenine (5-AcO-DMT)
* O-Pivalylbufotenine (5-t-BuCO-DMT)

5-Methoxytryptamines|

* 4-HO-5-MeO-DMT
* 5-MeO-2,N,N-TMT
* 5-MeO-DALT
* 5-MeO-DBT
* 5-MeO-DET
* 5-MeO-DiPT
* 5-MeO-DMT (mebufotenin)
* 5-MeO-DMT-d4
* 5-MeO-DPT
* 5-MeO-EiPT
* 5-MeO-MALT
* 5-MeO-MET
* 5-MeO-MiPT
* 5-MeO-MsBT
* 5-MeO-NiPT
* 5-MeO-NMT
* 5-MeO-T-NBOMe
* 5-MeO-T-NB3OMe
* 5-MeO-T (5-MT)
* ASR-3001 (5-MeO-iPALT)
* NB-5-MeO-DALT
* NB-5-MeO-MiPT

Other ring subs.|

* 2,N,N-TMT (2-methyl-DMT)
* 4,N,N-TMT (4-methyl-DMT)
* 5-Bromo-DMT
* 5-Chloro-DMT
* 5-Fluoro-DMT
* 5-Nitro-T (Nitro-I)
* 5-PhO-T (OVT2)
* 5-N,N-TMT (5-methyl-DMT)
* 7,N,N-TMT (7-methyl-DMT)
* 5-MeO-2,N,N-TMT
* 6-Fluoro-DMT
* 6-Hydroxy-DET (6-HO-DET)
* Bretisilocin (GM-2505; 5-fluoro-MET)
* NBoc-DMT (NB-DMT)

α-Alkyltryptamines|

* 4-HO-AMT
* 4-Methyl-AMT
* 5-Fluoro-AMT
* 6-Fluoro-AMT
* AMT (Indopan)
* α-Methylserotonin (5-HO-αMT)
* α,N,N-TMT (α-Me-DMT; Alpha-N)
* N-Hydroxy-AMT

* 5-Methoxy-α-alkyltryptamines: 5-MeO-AET
* 5-MeO-AMT (α,O-DMS; Alpha-O)
* α,N,O-TMS (5-MeO-α,N-DMT)
* α,N,N,O-TeMS (5-MeO-α,N,N-TMT)

Others|

* N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET)

* Structure undisclosed: CT-4201
* EB-002 (EB-373)
* MSP-1014
* MYCO-004

Cyclized|

* Ergolines/lysergamides (e.g., LSD)
* Ibogalogs (e.g., ibogainalog, tabernanthalog)
* O-Methylnordehydrobufotenine
* Partial ergolines (e.g., NDTDI, RU-28306, CT-5252)
* Piperidinylethylindoles (e.g., pip-T)
* Pyrrolidinylethylindoles (e.g., pyr-T, 5-MeO-pyr-T)
* Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI, MSP-2020)
* Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI), NEtPhOH-THPI)

Bioisosteres|

* Benzofurans (e.g., 5-MeO-DiBF (1-oxa-5-MeO-DiPT), dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT))
* Benzothiophenes (e.g., 3-APBT (1-thia-AMT))
* Indazolethylamines (e.g., AL-38022A, O-methyl-AL-34662)
* Indenylethylamines (e.g., C-DMT)
* Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175)
* MYCO-005
* Quinolinylethylamines (e.g., mefloquine)

Phenethylamines|

| Scalines|

* 2-Bromomescaline
* 4-D (4-trideuteromescaline)
* Allylescaline (AL)
* Beta-D (β-D; β-dideuteromescaline)
* Cyclopropylmescaline (CPM)
* Difluoroescaline (DFE)
* Difluoromescaline (DFM)
* N,N-Diformylmescaline
* Escaline (E)
* Fluoroescaline (FE)
* Fluoroproscaline (FP)
* N-Formylmescaline
* Isobuscaline (IB)
* Isoproscaline (IP)
* Mescaline (M; 3,4,5-TMPEA)
* Metadifluoromescaline (MDFM)
* Metaescaline (ME)
* Methallylescaline (MAL)
* N-Methylmescaline (M-M)
* Proscaline (P)
* Trichocereine (N,N-dimethylmescaline; MM-M)
* Trifluoroescaline (TFE)
* Trifluoromescaline (TFM)

* Thioscalines: 3-Thioasymbescaline (3-TASB)
* 3-Thioescaline (3-TE)
* 3-Thiomescaline (3-TM)
* 3-Thiometaescaline (3-TME)
* 4-Thioasymbescaline (4-TASB)
* 4-Thioescaline (4-TE)
* 4-Thiomescaline (4-TM)
* 5-Thioasymbescaline (5-TASB)
* Thiobuscaline (TB; 4-TB)
* Thioproscaline (TP; 4-TP)

* Others: 4-Desoxymescaline (desoxy)
* Jimscaline
* Tomscaline

|

2C-x|

* 2C-B
* 2C-Bu
* 2C-C
* 2C-CN
* 2C-CP
* 2C-D
* 2C-E
* 2C-EF
* 2C-F
* 2C-H
* 2C-I
* 2C-iBu
* 2C-iP
* 2C-N
* 2C-P
* 2C-Se
* 2C-Se-TFM
* 2C-tBu
* 2C-TFE
* 2C-TFM
* 2C-YN
* 2C-V

* 2C-T-x: 2C-T
* 2C-T-2
* 2C-T-3 (2C-T-20)
* 2C-T-4
* 2C-T-7
* 2C-T-8
* 2C-T-9
* 2C-T-13
* 2C-T-15
* 2C-T-16
* 2C-T-17
* 2C-T-19
* 2C-T-21
* 2C-T-21.5
* 2C-T-22
* 2C-T-25
* 2C-T-27
* 2C-T-28
* 2C-T-30
* CYB210010 (2C-T-TFM, 2C-T-36)

* 2C-O-x: 2C-O (2,4,5-TMPEA; TMPEA-2)
* 2C-O-4
* 2C-O-22

* Others: 2C-B-AN
* 2C-DB
* 2C-G-x (e.g., 2C-G-3, 2C-G-5)
* β-Keto-2C-B (βk-2C-B)
* β-Keto-2C-I (βk-2C-I)
* β-Methyl-2C-B (BMB)
* BOx (e.g., BOB, BOD, BOHB)
* HOT-x (e.g., HOT-2, HOT-7, HOT-17)
* N-Ethyl-2C-B
* TWEETIOs (e.g., 2CB-2-EtO, 2CD-2-EtO, 2CD-5-EtO, 2CE-5-EtO, 2CE-5iPrO, 2CT2-2-EtO, ASR-2001 (2CB-5-PrO))

3C-x|

* 3C-AL
* 3C-BZ
* 3C-DFE
* 3C-E
* 3C-FP
* 3C-MAL
* 3C-P
* TMA (3C-M)

DOx|

* DOAM
* DOB
* DOBU
* DOC
* DOEF
* DOET
* DOH (2,5-DMA)
* DOI
* DOIB
* DOIP
* DOM
* DON
* DOPR
* DOTFM
* DOYN

* Aleph-x (DOT-x): Aleph (DOT)
* Aleph-2
* Aleph-4
* Aleph-6
* Aleph-7

* TMA-2 and derivatives (Mxx): MALM
* MEM
* MDFEM
* MFEM
* MIPM
* MMALM
* MPM
* MTFEM
* TMA-2

* Others: DODB
* DODC
* DOM-NBOMe
* DOTMA
* Ganeshas (G-x) (e.g., Ganesha (G, G-0), G-3, G-5)
* MME (TMA2-5-EtO)
* N-Hydroxy-DOM

4C-x|

* 4C-B
* 4C-D (Ariadne)
* 4C-I
* 4C-P (4C-Pr)
* 4C-T-2
* 4C-TFM

Ψ-PEA|

* 2,4,6-TMPEA-NBOMe
* Ψ-2C-DFMO (ψ-2C-O-35)
* Ψ-2C-T-4
* Ψ-DODFMO
* Ψ-DOM
* TMA-6 (Ψ-TMA-2)

MDxx|

* 5-Methyl-MDA
* 6-Methyl-MDA
* DMMDA
* DMMDA-2
* EIDA
* EMDA-2
* IDA
* Lophophine (MMDPEA)
* Lys-MDA
* MDA (tenamfetamine)
* MDHMA (FLEA; MDMOH)
* MDMA (midomafetamine; ecstasy)
* MDOH
* MMDA
* MMDA-2
* MMDA-3a
* MMDA-3b
* MMDMA
* N-t-BOC-MDMA
* (R)-MDMA

FLY|

* 2C-B-FLY
* 2C-B-BUTTERFLY
* 2C-B-DragonFLY
* 2CBFly-NBOMe
* Bromo-DragonFLY
* DOB-FLY
* DOH-FLY
* TFMFly

* Hemi/semi-FLY drugs: 2CB-5-hemiFLY
* DOH-5-hemiFLY (semi-fly; SF)
* DOB-5-hemiFLY (bromo-semi-fly; B-SF)

25x-NB (NBOMes)|

* 25x-NBOMe: 25B-NBOMe
* 25C-NBOMe
* 25CN-NBOMe
* 25D-NBOMe
* 25E-NBOMe
* 25F-NBOMe
* 25G-NBOMe
* 25H-NBOMe
* 25I-NBOMe
* 25iP-NBOMe
* 25N-NBOMe
* 25O-NBOMe
* 25P-NBOMe
* 25T-NBOMe
* 25T2-NBOMe
* 25T4-NBOMe
* 25T7-NBOMe
* 25TFM-NBOMe

* 25x-NBOH: 25B-NBOH
* 25C-NBOH
* 25CN-NBOH
* 25E-NBOH
* 25I-NBOH

* Others: 2,4,6-TMPEA-NBOMe
* 25B-NB (N-benzyl-2C-B)
* 2C-B-AN
* 2C2-NBOMe
* 2CBCB-NBOMe
* 2CBFly-NBOMe
* DOM-NBOMe
* NBOMe-escaline
* NBOMe-mescaline
* TGF-8027

Others|

* 25B-NAcPip
* 2-DM-DOM
* 4-HA
* 5-DM-DOM
* Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F, F-2, F-22)
* Benzothiophenes (e.g., 5-APBT, 6-APBT)
* CT-5172
* DMAs (e.g., 2,4-DMA, 3,4-DMA)
* Fenfluramine
* MMA (3-MeO-4-MA)
* Norfenfluramine
* PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA)
* PMA (4-MA)
* Thio-2Cs (e.g., 2C-5-TOET)
* Thio-DOx (e.g., 2-TOM, 5-TOET, 5-TOM, TOMSO)
* TMAs (e.g., TMA-3, TMA-4, TMA-5)
* ZDCM-04 (DOC-fenethylline)

* Structure undisclosed: CYB005

Cyclized|

* 1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline)
* 2-Aminoindanes (e.g., DOM-AI)
* 3-Benzazepines (e.g., lorcaserin)
* 3-Phenylpiperidines (e.g., LPH-5, LPH-48)
* Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline)
* Benzoxepins (e.g., BBOX, IBOX, TFMBOX)
* DMBMPP (juncosamine)
* Ergolines/lysergamides (e.g., LSD)
* Glaucine
* Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA)
* Phenylcyclopropylamines (e.g., DMCPA, TMT)
* Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex)
* Pyridopyrroloquinoxalines (e.g., IHCH-7113)
* Z3517967757
* ZC-B

Lysergamides|

* No substitutions: Ergine (LSA, LA-111)
* Isoergine (iso-LSA, iso-LA)

* Amide-substituted lysergamides: DAL
* DAM (DAM-57)
* DiPLA
* DPL
* EcPLA
* EiPLA
* EPLA (LEP; LEP-57)
* Ergometrine (ergonovine, ergobasine)
* ETFELA
* iPLA
* LA-3Cl-SB (Cl-LSB)
* LAE (LAE-32)
* LAM
* LAMPA
* LAP
* LME (LME-54)
* LMP (LMP-55)
* LPD (LPD-824)
* LSB
* LSD (LSD-25, METH-LAD; lysergide)
* LSD-Pip
* LSDP (DPL)
* LSH (LAH)
* LSM (LSM-775)
* LSP
* LSZ (LA-SS-Az)
* Lysergic acid pyrrolinide (LPN)
* Methylergometrine (methylergonovine, methylergobasine)
* MiPLA

* 6-Alkyllysergamides: BU-LAD
* CE-LAD (CHLORETH-LAD)
* CPM-LAD
* CYP-LAD (TRALA-22)
* ETH-LAD
* FLUORETH-LAD (FE-LAD)
* FP-LAD
* IP-LAD
* NBOMe-LAD
* PARGY-LAD
* PRO-LAD

* 1-Alkyllysergamides (prodrugs): Methysergide (1-methylmethylergonovine; UML-491)
* MLA-74 (1-methyl-LAE)
* MLD-41 (1-methyl-LSD)
* MPD-75 (1-methyl-LPD)
* OML-632 (1-hydroxymethyl-LSD)

* 1-Acyllysergamides (prodrugs): 1-Formyl-LSD
* 1B-LSD
* 1BP-LSD
* 1Bz-LSD
* 1cP-AL-LAD
* 1cP-LSD
* 1cP-MiPLA
* 1D-AL-LAD
* 1D-LSD
* 1DD-LSD
* 1F-LSD
* 1Fe-LSD
* 1H-LSD
* 1P-AL-LAD
* 1P-ETH-LAD
* 1P-LSD
* 1P-MiPLA
* 1S-LSD
* 1SB-LSD (1BS-LSD)
* 1T-AL-LAD
* 1T-LSD
* 1V-LSD
* ALA-10 (1-acetyl-LAE; 1A-LAE)
* ALD-52 (1-acetyl-LSD; 1A-LSD)

* Others: 2,3-Dihydro-LSD
* 12-Hydroxy-LSD
* 12-Methoxy-LSD

* Bioisosteres: JRT (isoindole-LSD)

Others|

* Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP)
* Dihydrobenzoxazines (e.g., efavirenz)
* Phenoxyethylamines (e.g., CT-4719, ORG-37684)
* Pyridopyrroloquinoxalines (e.g., IHCH-7113)
* Quinazolinylethylamines (e.g., RH-34)

* Structure undisclosed: BMB-202
* EGX-A
* EGX-B
* HBL20016
* Lucid-PSYCH (Lucid-201)
* MSP-4018
* MSP-4019
* MSP-4020

Natural sources|

* Tryptamines: Acacia spp. (e.g., Acacia acuminata, Acacia confusa)
* Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna), Dipolopterys cabrerana (chaliponga, chacruna), Mimosa tenuiflora (Mimosa hostilis; jurema))
* Brosimum (e.g., Brosimum acutifolium (takini))
* Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene), Anadenanthera colubrina (vilca, cebil))
* Incilius alvarius (Bufo alvarius; Colorado River toad, Sonoran Desert toad; bufo)
* Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis, Psilocybe mexicana (teonanacatl))

* Phenethylamines: Pachycereus pringlei (saguesa, elephant cactus, cardon)
* Peyote (Lophophora williamsii; peyotl)
* Echinopsis cacti (e.g., San Pedro, Peruvian torch)

* Lysergamides: Achnatherum robustum (sleepy grass)
* Epichloë spp.
* Ergot (Claviceps) (e.g., Claviceps purpurea, Claviceps paspali)
* Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea), Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa, Turbina Corymbosa), Argyreia nervosa (Hawaiian baby woodrose; HBWR))
* Periglandula spp. (e.g., Periglandula ipomoeae, Periglandula clandestina)

* See also: Hallucinogens
* Entactogens
* Tryptamines
* Phenethylamines
* Ergolines and lysergamides
* Serotonin receptor modulators
* List of psychedelic drugs

* v
* t
* e

Serotonin receptor modulators

5-HT1|

| 5-HT1A|

* Agonists: 8-OH-DPAT
* Adatanserin
* Amphetamine
* Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine)
* Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone)
* Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone)
* Bay R 1531
* Befiradol
* BMY-14802
* Cannabidiol
* Dimemebfe
* Dopamine
* Ebalzotan
* Eltoprazine
* Enciprazine
* Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide)
* F-11461
* F-12826
* F-13714
* F-14679
* F-15063
* F-15,599
* Flesinoxan
* Flibanserin
* Flumexadol
* Hypidone
* Lesopitron
* LY-293284
* LY-301317
* mCPP
* MKC-242
* Naluzotan
* NBUMP
* Osemozotan
* Oxaflozane
* Pardoprunox
* Piclozotan
* Rauwolscine
* Repinotan
* Roxindole
* RU-24,969
* S-14,506
* S-14671
* S-15535
* Sarizotan
* Serotonin (5-HT)
* SSR-181507
* Sunepitron
* Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin)
* TGBA01AD
* U-92,016-A
* Urapidil
* Vilazodone
* Xaliproden
* Yohimbine

* Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole)
* AV965
* Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol)
* BMY-7,378
* CSP-2503
* Dotarizine
* Ergolines (e.g., metergoline)
* FCE-24379
* Flopropione
* GR-46611
* Isamoltane
* Lecozotan
* Mefway
* Metitepine (methiothepin)
* MIN-117 (WF-516)
* MPPF
* NAN-190
* Robalzotan
* S-15535
* SB-649,915
* SDZ 216-525
* Spiperone
* Spiramide
* Spiroxatrine
* UH-301
* WAY-100135
* WAY-100635
* Xylamidine

* Unknown/unsorted: Acetryptine
* Carvedilol
* Ergolines (e.g., ergometrine (ergonovine))

5-HT1B|

* Agonists: Anpirtoline
* CGS-12066A
* CP-93129
* CP-94253
* CP-122,288
* CP-135807
* Eltoprazine
* Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)
* mCPP
* RU-24,969
* Serotonin (5-HT)
* Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan)
* TFMPP
* Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT)
* Vortioxetine

* Antagonists: AR-A000002
* Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol)
* Elzasonan
* Ergolines (e.g., metergoline)
* GR-127935
* Isamoltane
* LY-393558
* Metitepine (methiothepin)
* SB-216641
* SB-224289
* SB-236057
* Yohimbine

* Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

5-HT1D|

* Agonists: CP-122,288
* CP-135807
* CP-286601
* Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide)
* Chemistry:GR-46611
* L-694247
* Chemistry:L-772405
* mCPP
* PNU-109291
* PNU-142633
* Serotonin (5-HT)
* TGBA01AD
* Triptans (e.g., almotriptan, avitriptan, donitriptan, [[Chemistry:Eleeletriptan, Frovatriptan|frovatriptan]], naratriptan, rizatriptan, sumatriptan, zolmitriptan)
* Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT)

* Antagonists: Alniditan
* BRL-15,572
* Elzasonan
* Ergolines (e.g., metergoline)
* GR-127935
* Ketanserin
* LY-310762
* LY-367642
* LY-393558
* LY-456219
* LY-456220
* Metitepine (methiothepin)
* Mianserin
* Ritanserin
* Yohimbine
* Ziprasidone

* Unknown/unsorted: Acetryptine
* Ergolines (e.g., lisuride, lysergol, pergolide)

5-HT1E|

* Agonists: BRL-54443
* Ergolines (e.g., methysergide)
* Serotonin (5-HT)
* Triptans (e.g., eletriptan)
* Tryptamines (e.g., tryptamine)

* Antagonists: Metitepine (methiothepin)

* Unknown/unsorted: ErgIrindaloneolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)

5-HT1F|

* Agonists: BRL-54443
* CP-122,288
* Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide)
* Lasmiditan
* LY-334370
* Serotonin (5-HT)
* Triptans (e.g., eletriptan, naratriptan, sumatriptan)
* Tryptamines (e.g., 5-MT)

* Antagonists: Metitepine (methiothepin)
* Mianserin

5-HT2|

| 5-HT2A|

* Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe)
* 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)
* 2C-B-FLY
* 2CB-Ind
* 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)
* α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)
* AL-34662
* AL-37350A
* Bromo-DragonFLY
* Dimemebfe
* DMBMPP
* DOx (e.g., DOB, DOC, DOI, DOM)
* Efavirenz
* Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide)
* Flumexadol
* IHCH-7113
* Jimscaline
* Lorcaserin
* MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)
* O-4310
* Oxaflozane
* PHA-57378
* PNU-22394
* PNU-181731
* RH-34
* SCHEMBL5334361
* Phenethylamines (e.g., lophophine, mescaline)
* Piperazines (e.g., BZP, quipazine, TFMPP)
* Serotonin (5-HT)
* TCB-2
* TFMFly
* Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

* Antagonists: 5-I-R91150
* 5-MeO-NBpBrT
* AC-90179
* Adatanserin
* Altanserin
* Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine)
* AMDA
* Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine)
* Chlorprothixene
* Cinanserin
* CSP-2503
* Deramciclane
* Dotarizine
* Eplivanserin
* Ergolines (e.g., amesergide, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)
* Fananserin
* Flibanserin
* Glemanserin
* Irindalone
* Ketanserin
* KML-010
* Landipirdine
* LY-393558
* mCPP
* Medifoxamine
* Metitepine (methiothepin)
* MIN-117 (WF-516)
* Naftidrofuryl
* Nantenine
* Nelotanserin
* Opiranserin (VVZ-149)
* Pelanserin
* Phenoxybenzamine
* Pimavanserin
* Pirenperone
* Pizotifen
* Pruvanserin
* Rauwolscine
* Ritanserin
* Roluperidone
* S-14671
* Sarpogrelate
* Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone)
* SR-46349B
* TGBA01AD
* Teniloxazine
* Temanogrel
* Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine)
* Tricyclic antidepressants (e.g., amitriptyline)
* Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine)
* Volinanserin
* Xylamidine
* Yohimbine

* Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline)

5-HT2B|

* Agonists: 4-Methylaminorex
* Aminorex
* Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine)
* BW-723C86
* DOx (e.g., DOB, DOC, DOI, DOM)
* Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)
* Lorcaserin
* MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)
* Piperazines (e.g., TFMPP)
* PNU-22394
* Ro60-0175
* Serotonin (5-HT)
* Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

* Antagonists: Agomelatine
* Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone)
* Cyproheptadine
* EGIS-7625
* Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine)
* Ketanserin
* LY-393558
* mCPP
* Metadoxine
* Metitepine (methiothepin)
* Pirenperone
* Pizotifen
* Propranolol
* PRX-08066
* Rauwolscine
* Ritanserin
* RS-127445
* Sarpogrelate
* SB-200646
* SB-204741
* SB-206553
* SB-215505
* SB-221284
* SB-228357
* SDZ SER-082
* Tegaserod
* Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)
* Trazodone
* Typical antipsychotics (e.g., chlorpromazine)
* TIK-301
* Yohimbine

* Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT2C|

* Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)
* 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)
* α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)
* A-372159
* AL-38022A
* Alstonine
* CP-809101
* Dimemebfe
* DOx (e.g., DOB, DOC, DOI, DOM)
* Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide)
* Flumexadol
* Lorcaserin
* MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)
* MK-212
* ORG-12962
* ORG-37684
* Oxaflozane
* PHA-57378
* Phenethylamines (e.g., lophophine, mescaline)
* Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP)
* PNU-22394
* PNU-181731
* Ro60-0175
* Ro60-0213
* Serotonin (5-HT)
* Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)
* Vabicaserin
* WAY-629
* WAY-161503
* YM-348

* Antagonists: Adatanserin
* Agomelatine
* Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine)
* Captodiame
* CEPC
* Cinanserin
* Cyproheptadine
* Deramciclane
* Desmetramadol
* Dotarizine
* Eltoprazine
* Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)
* Etoperidone
* Fluoxetine
* FR-260010
* Irindalone
* Ketanserin
* Ketotifen
* Latrepirdine (dimebolin)
* Medifoxamine
* Metitepine (methiothepin)
* Nefazodone
* Pirenperone
* Pizotifen
* Propranolol
* Ritanserin
* RS-102221
* S-14671
* SB-200646
* SB-206553
* SB-221284
* SB-228357
* SB-242084
* SB-243213
* SDZ SER-082
* Tedatioxetine
* Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine)
* TIK-301
* Tramadol
* Trazodone
* Tricyclic antidepressants (e.g., amitriptyline, nortriptyline)
* Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine)
* Xylamidine

* Unknown/unsorted: Efavirenz
* Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))

5-HT3–7|

| 5-HT3|

* Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol)
* m-CPBG
* Phenylbiguanide
* Piperazines (e.g., BZP, mCPP, quipazine)
* RS-56812
* Serotonin (5-HT)
* SR-57227
* SR-57227A
* Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ))
* Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane)
* YM-31636

* Antagonists: Alosetron
* Chemistry:Arazasetron
* AS-8112
* Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine)
* Azasetron
* Batanopride
* Bemesetron (MDL-72222)
* Bupropion
* Cilansetron
* CSP-2503
* Dazopride
* Dolasetron
* Galanolactone
* Granisetron
* Hydroxybupropion
* Lerisetron
* Memantine
* Ondansetron
* Palonosetron
* Ramosetron
* Renzapride
* Ricasetron
* Tedatioxetine
* Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)
* Thujone
* Tropanserin
* Tropisetron
* Typical antipsychotics (e.g., loxapine)
* Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon)
* Vortioxetine
* Zacopride
* Zatosetron

* Unknown/unsorted: LY-53857
* Piperazines (e.g., naphthylpiperazine)

5-HT4|

* Agonists: 5-MT
* BIMU8
* Capeserod
* Cinitapride
* Cisapride
* CJ-033466
* Dazopride
* Metoclopramide
* Minesapride
* Mosapride
* Prucalopride
* PRX-03140
* Renzapride
* RS-67,333
* RS-67,506
* Serotonin (5-HT)
* Tegaserod
* Usmarapride
* Velusetrag
* Zacopride

* Antagonists: GR-113808
* GR-125487
* L-Lysine
* Piboserod
* RS-39604
* RS-67532
* SB-203186
* SB-204070

5-HT5A|

* Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD)
* Serotonin (5-HT)
* Tryptamines (e.g., 5-CT)
* Valerenic acid

* Antagonists: Asenapine
* Latrepirdine (dimebolin)
* Metitepine (methiothepin)
* Ritanserin
* SB-699551

* Unknown/unsorted: Ergolines (e.g., metergoline, methysergide)
* Piperazines (e.g., naphthylpiperazine)

5-HT6|

* Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide)
* Hypidone
* Serotonin (5-HT)
* Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, ST-1936, tryptamine)
* WAY-181187
* WAY-208466

* Antagonists: ABT-354
* Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone)
* AVN-101
* AVN-211
* AVN-322
* AVN-397
* BGC20-760
* BVT-5182
* BVT-74316
* Cerlapirdine
* EGIS-12,233
* GW-742457
* Idalopirdine
* Ketanserin
* Landipirdine
* Latrepirdine (dimebolin)
* Masupirdine
* Metitepine (methiothepin)
* MS-245
* PRX-07034
* Ritanserin
* Ro 04-6790
* Ro 63-0563
* SB-258585
* SB-271046
* SB-357134
* SB-399885
* SB-742457
* Tetracyclic antidepressants (e.g., amoxapine, mianserin)
* Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline)
* Typical antipsychotics (e.g., chlorpromazine, loxapine)

* Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide)
* Piperazines (e.g., naphthylpiperazine)

5-HT7|

* Agonists: 8-OH-DPAT
* AS-19
* Bifeprunox
* E-55888
* Ergolines (e.g., LSD)
* LP-12
* LP-44
* LP-211
* RU-24,969
* Sarizotan
* Serotonin (5-HT)
* Triptans (e.g., frovatriptan)
* Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)

* Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine)
* Butaclamol
* DR-4485
* EGIS-12,233
* Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)
* JNJ-18038683
* Ketanserin
* LY-215,840
* Metitepine (methiothepin)
* Ritanserin
* SB-258719
* SB-258741
* SB-269970
* SB-656104
* SB-656104A
* SB-691673
* SLV-313
* SLV-314
* Spiperone
* Chemistry:SSR-181507
* Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
* Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine)
* Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide)
* Vortioxetine

* Unknown/unsorted: Ergolines (e.g., lisuride, pergolide)
* Piperazines (e.g., naphthylpiperazine)

* See also: Receptor/signaling modulators
* Adrenergics
* Dopaminergics
* Melatonergics
* Monoamine reuptake inhibitors and releasing agents
* Monoamine metabolism modulators
* Monoamine neurotoxins

* v
* t
* e

Chemical classes of psychoactive drugs

Stimulants|

* Amphetamine-type/dopamine releasing agents: Alkylamines
* Cycloalkylaminopropanes
* Arylpiperazines
* Benzylpiperazines
* Phenylpiperazines
* Phenethylamines
* Aminorexes/phenyloxazolamines
* Amphetamines/α-methylphenethylamines
* Cathinones/β-ketoamphetamines
* β-Hydroxyamphetamines/cathinols
* Naphthylaminopropanes
* Phentermines
* Phenylisobutylamines/α-ethylphenethylamines
* α-Propylphenethylamines
* Phenylmorpholines/phenmetrazines
* Thiopropamines/thienylaminopropanes

* Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines
* Phenidates/benzylpiperidines
* Phenylethylpyrrolidines
* Pyrrolidinophenones
* Phenyltropanes/cocaine analogues

* Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues
* Phenylpiracetams

* Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines

* Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues

Depressants|

* GABAA receptor positive allosteric modulators: Alcohols/ethanol analogues
* Barbiturates
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines
* Carbamates
* Ethers
* Neuroactive steroids
* Nonbenzodiazepines
* β-Carbolines
* Cyclopyrrolones
* Imidazopyridines
* Pyrazolopyrimidines
* Phenols
* Piperidinediones
* Quinazolinones

* GABAA receptor agonists: Isoxazoles

* GHB receptor agonists: 1,4-Butanediols

* α2δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids

* Opioids/μ-opioid receptor agonists: Benzimidazoles
* Nitazenes
* Fentanyl analogues/phenylpiperidines
* Mitragyna alkaloids
* Morphinans/phenanthrenes
* Opiates/opium alkaloids
* Utopioids

* Antihistamines/H1 receptor antagonists: Benzimidazoles
* Diarylmethanes
* Ethylenediamines
* Tricyclics
* Dibenzocycloheptenes

Hallucinogens|

* Serotonergic psychedelics/serotonin 5-HT2A receptor agonists: Arylpiperazines
* Phenylpiperazines
* Quinolinylpiperazines
* Cyclized phenethylamines
* 3-Benzazepines
* Cyclized tryptamines
* Azepinoindoles
* Ibogalogs
* Iboga alkaloids
* β-Carbolines
* Harmala alkaloids
* Ergolines
* Lysergamides
* Simplified/partial lysergamides
* Phenethylamines (methoxyphenethylamines)
* 2Cs
* 25-NB/NBOMes
* 2C-Os
* 2C-Ts
* HOT-x
* TWEETIOs
* Amphetamines/α-methylphenethylamines
* 3Cs
* Dimethoxyamphetamines/DMAs
* DOx
* Alephs
* Ethylenedioxyamphetamines/EDxx
* Methylenedioxyamphetamines/MDxx
* Trimethoxyamphetamines/TMAs
* BOx
* FLYs/benzofurans
* Phenylisobutylamines/α-ethylphenethylamines
* 4Cs
* Scalines
* Ψ-PEAs
* Tryptamines
* α-Alkyltryptamines
* α-Alkyl-β-ketotryptamines
* 4-Hydroxytryptamines
* 5-Hydroxytryptamines
* 5-Methoxytryptamines
* Miscellaneous

* Dissociatives/NMDA receptor antagonists: Adamantanes
* Arylcyclohexylamines
* Diarylethylamines
* Morphinans

* κ-Opioid receptor agonists: Benzomorphans
* Salvinorins

* GABAA receptor agonists: Isoxazoles

* Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes
* Tropanes

* Others: Cyclized tryptamines
* Azepinoindoles
* Iboga alkaloids
* (Phyto)cannabinoids

Entactogens|

* Serotonin releasing agents: Phenethylamines
* 2-Aminoindanes
* 2-Aminotetralins
* Amphetamines
* Benzofuranylaminopropanes
* Benzothiophenylaminopropanes
* Ethylenedioxyamphetamines/EDxx
* Indanylaminopropanes
* Indolylaminopropanes
* Methylenedioxyamphetamines/MDxx
* Tetralinylaminopropanes
* Tryptamines
* α-Alkyltryptamines
* Miscellaneous

Psychiatric drugs|

* Anxiolytics: Azapirones
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines

* Antidepressants: Tricyclic antidepressants
* Dibenzazepines
* Dibenzocycloheptenes
* Dibenzothiepins
* Dibenzoxazepines
* Dibenzoxepins
* Tetracyclic antidepressants

* Antipsychotics/dopamine D2 receptor antagonists or partial agonists: Benzamides
* Benzimidazoles
* Benzisothiazoles
* Benzisoxazoles
* Butyrophenones
* Diphenylbutylpiperidines
* Phenylpiperazines
* Tricyclics
* Dibenzazepines
* Dibenzodiazepines
* Dibenzothiazepines
* Dibenzothiepins
* Dibenzoxazepines
* Phenothiazines
* Thienobenzodiazepines

* Mood stabilizers/anticonvulsants: Gabapentinoids
* Tricyclics
* Dibenzazepines
* Valproates

Others|

* Nootropics: Racetams
* Phenylpiracetams

* Miscellaneous: 3-Benzazepines
* Adamantanes
* Catecholamines
* Tetrahydroisoquinolines
* Yohimbans

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Original source: https://en.wikipedia.org/wiki/Substituted tryptamine. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Substituted_tryptamine&oldid=4531597"
*[MAOI]: monoamine oxidase inhibitor
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*[NBOMe]: NB: N-benzyl; OMe: methoxy
*[NBOH]: NB: N-benzyl; OH: hydroxy