Substituted tryptamine

Short description: Class of indoles

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

Substituted tryptamines, or serotonin 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, 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: LSD, ibogaine, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.

## Contents

* 1 List of substituted tryptamines
* 2 List of substituted α-alkyltryptamines
* 3 Related compounds
* 4 Further reading
* 5 See also
* 6 References

## List of substituted tryptamines

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

Selected tryptamines Chemical structure  | Short Name  | Origin  | Ring Substitution  | RN1 | RN2 | Full Name  | CAS Number

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| Tryptamine | Animals, plants, fungi | H | H | H | 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine | 61-54-1
| 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 | Animals, plants | 5-OH | H | H | 5-hydroxytryptamine | 50-67-9
| Nω-Methylserotonin (norbufotenin) | Plants | 5-OH | H | CH3 | 5-hydroxy-N-methyltryptamine | 1134-01-6
| Bufotenin | Animals, plants, fungi | 5-OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyltryptamine | 487-93-4
| Bufotenidine | Amphibians | 5-O− | (CH3)3 | 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate | 487-91-2
| Melatonin | Animals, plants, microbes | 5-OCH3 | H | O=C-CH3 | 5-methoxy-N-acetyltryptamine | 73-31-4
| N-Acetylserotonin | 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
| 4-HO-NMT | Fungi | 4-OH | H | CH3 | 4-hydroxy-N-methyltryptamine | 28363-70-4
| Psilocin | Fungi | 4-OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyltryptamine | 520-53-6
| Norbaeocystin | Fungi | 4-OPO3H2 | H | H | 4-phosphoryloxy-tryptamine | 21420-59-7
| Baeocystin | Fungi | 4-OPO3H2 | H | CH3 | 4-phosphoryloxy-N-methyl-tryptamine | 21420-58-6
| Psilocybin | Fungi | 4-OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyltryptamine | 520-52-5
| Aeruginascin | Fungi | 4-OPO3H2 | (CH3)3 | [3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate | 114264-95-8
| DMT | Animals, plants | H | CH3 | CH3 | N,N-dimethyltryptamine | 61-50-7
| Lespedamine | Plants | 1-OCH3 | CH3 | CH3 | 1-methoxy-N,N-dimethyltryptamine | 4335-93-7
| 5-MeO-DMT | 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 | 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
| Acetryptine | artificial  | 5-COCH3 | H  | H  | 5-Acetyltryptamine  | 3551-18-6
| 5-BT | artificial  | 5-OCH2C6H5 | H  | H  | 5-Benzyloxytryptamine  | 20776-45-8
| 5-CT | artificial  | 5-CONH2 | H  | H  | 5-Carboxamidotryptamine  | 74885-09-9
| 5-(Nonyloxy)tryptamine | 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
| NET | artificial  | H  | H  | CH2CH3 | N-ethyltryptamine  | 61-53-0
| NiPT  | artificial  | H  | H  | CH(CH3)2 | N-isopropyltryptamine  | 14121-10-9
| NcPT  | artificial  | H  | H  | C3H5 | N-cyclopropyltryptamine  |
| NSBT  | artificial  | H  | H  | CH(CH3)CH2CH3 | N-sec-butyltryptamine  |
| NTBT | artificial  | H  | H  | C(CH3)3 | N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine  |
| 5-MT-NBOMe  | artificial  | 5-OCH3 | H  | CH2C6H4(o-OCH3)  | 5-methoxy-N-(ortho-methoxybenzyl)tryptamine  | 1335331-37-7
| 5-MT-NB3OMe [2] | 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 [3] | 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-tetrafluoropropoxy)benzyl)ethanamine  | 467459-31-0
| Z2876442907[4] | artificial  | 4-CH3 | H  | CH2(C3HNS)COOCH2CH3 | ethyl 2-({[2-(4-methyl-1H-indol-3-yl)ethyl]amino}methyl)-1,3-thiazole-5-carboxylate  |
| Pyr-T | artificial | H | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole | 14008-96-9
| 4-HO-pyr-T | artificial | 4-OH | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol | 63097-26-7
| 5-MeO-pyr-T | artificial | 5-OCH3 | (CH2)4 | 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole | 3949-14-2
| 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
| MET | artificial  | H  | CH3 | CH2CH3 | N-Methyl-N-ethyltryptamine  | 5599-69-9
| MPT  | artificial  | H  | CH3 | CH2CH2CH3 | N-Methyl-N-propyltryptamine  | 850032-72-3
| MiPT | artificial  | H  | CH3 | CH(CH3)2 | N-Methyl-N-isopropyltryptamine  | 96096-52-5
| McPT  | artificial  | H  | CH3 | C3H5 | N-Methyl-N-cyclopropyltryptamine  | 1373918-63-8
| EcPT  | artificial  | H  | CH2CH3 | C3H5 | N-ethyl-N-cyclopropyltryptamine  |
| PcPT  | artificial  | H  | CH2CH2CH3 | C3H5 | N-propyl-N-cyclopropyltryptamine  |
| iPcPT  | artificial  | H  | CH(CH3)2 | C3H5 | N-isopropyl-N-cyclopropyltryptamine  |
| DcPT  | artificial  | H  | C3H5 | C3H5 | N,N-dicyclopropyltryptamine  | 1373918-62-7
| MBT | artificial  | H  | CH3 | (CH2)3CH3 | N-Methyl-N-butyltryptamine  | 848130-12-1
| MSBT  | artificial  | H  | CH3 | CH(CH3)CH2CH3 | N-Methyl-N-sec-butyltryptamine  |
| MiBT  | artificial  | H  | CH3 | CH2CH(CH3)2 | N-Methyl-N-iso-butyltryptamine  |
| McPMT  | artificial  | H  | CH3 | CH2C3H5 | N-Methyl-N-(cyclopropylmethyl)tryptamine  |
| DET | artificial  | H  | CH2CH3 | CH2CH3 | N,N-diethyltryptamine  | 61-51-8
| EPT | artificial  | H  | CH2CH3 | CH2CH2CH3 | N-Ethyl-N-propyltryptamine  | 850032-68-7
| EiPT | artificial  | H  | CH2CH3 | CH(CH3)2 | N-Ethyl-N-isopropyltryptamine  | 848130-11-0
| DPT | artificial  | H  | CH2CH2CH3 | CH2CH2CH3 | N,N-dipropyltryptamine  | 61-52-9
| PiPT | artificial  | H  | CH2CH2CH3 | CH(CH3)2 | N-Propyl-N-isopropyltryptamine  | 1354632-00-0
| DiPT | artificial  | H  | CH(CH3)2 | CH(CH3)2 | N,N-diisopropyltryptamine  | 14780-24-6
| EBT  | artificial  | H  | CH2CH3 | (CH2)3CH3 | N-ethyl-N-butyltryptamine  |
| PBT  | artificial  | H  | CH2CH2CH3 | (CH2)3CH3 | N-propyl-N-butyltryptamine  |
| iPsBT  | artificial  | H  | CH(CH3)2 | CH(CH3)CH2CH3 | N-isopropyl-N-sec-butyltryptamine  |
| DBT | artificial  | H  | (CH2)3CH3 | (CH2)3CH3 | N,N-dibutyltryptamine  | 15741-77-2
| DIBT  | artificial  | H  | CH2CH(CH3)2 | CH2CH(CH3)2 | N,N-diisobutyltryptamine  | 63938-64-7
| DSBT  | artificial  | H  | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | N,N-disecbutyltryptamine  |
| MALT | artificial  | H  | CH3 | H2C=CH-CH2 | N-methyl-N-allyltryptamine  | 1366416-29-6
| DALT  | artificial  | H  | H2C=CH-CH2 | H2C=CH-CH2 | N,N-diallyltryptamine  | 60676-77-9
| ALiPT  | artificial  | H  | H2C=CH-CH2 | CH(CH3)2 | N-allyl-N-isopropyltryptamine  |
| 2-Methyl-DMT | artificial  | 2-CH3 | CH3 | CH3 | (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine  | 1080-95-1
| 2-Me-DET | artificial  | 2-CH3 | CH2CH3 | CH2CH3 | N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine  | 26628-88-6
| 4-Amino-DMT [5] | artificial  | 4-NH2 | CH3 | CH3 | 4-amino-N,N-dimethyltryptamine  | 60331-61-5
| 4-Methyl-DMT  | artificial  | 4-CH3 | CH3 | CH3 | 4,N,N-trimethyltryptamine  | 28289-23-8
| 4-MeO-DMT | artificial  | 4-OCH3 | CH3 | CH3 | 4-methoxy-N,N-dimethyltryptamine  | 3965-97-7
| 4-MeO-MiPT | artificial  | 4-OCH3 | CH3 | CH(CH3)2 | 4-methoxy-N-methyl-N-isopropyltryptamine  | 96096-53-6
| 4-MeO-DiPT  | artificial  | 4-OCH3 | CH(CH3)2 | CH(CH3)2 | 4-methoxy-N,N-diisopropyltryptamine  |
| 4-AcO-DMT  | 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
| 4-HO-MET | artificial  | 4-OH  | CH3 | CH2CH3 | 4-hydroxy-N-methyl-N-ethyltryptamine  | 77872-41-4
| 4-Acetoxy-MET | artificial  | 4-OCOCH3 | CH3 | CH2CH3 | 4-acetoxy-N-methyl-N-ethyltryptamine  | 1445751-40-5
| 4-PO-MET  | artificial  | 4-OPO3H2 | CH3 | CH2CH3 | 4-phosphoryloxy-N-methyl-N-ethyltryptamine  |
| 4-HO-DET | artificial  | 4-OH  | CH2CH3 | CH2CH3 | 4-hydroxy-N,N-diethyltryptamine  | 22204-89-3
| 4-Acetoxy-DET | artificial  | 4-OCOCH3 | CH2CH3 | CH2CH3 | 4-acetoxy-N,N-diethyltryptamine  | 1135424-15-5
| 4-PO-DET | 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
| 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
| 4-HO-MiPT | artificial  | 4-OH  | CH(CH3)2 | CH3 | 4-hydroxy-N-isopropyl-N-methyltryptamine  | 77872-43-6
| 4-Acetoxy-MiPT | artificial  | 4-OCOCH3 | CH3 | CH(CH3)2 | 4-acetoxy-N-methyl-N-isopropyltryptamine  | 1024612-25-6
| 4-HO-MALT[6] | artificial  | 4-OH  | CH3 | H2C=CH-CH2 | 4-hydroxy-N-Methyl-N-allyltryptamine  |
| 4-AcO-MALT[7] | artificial  | 4-OCOCH3 | CH3 | H2C=CH-CH2 | 4-acetoxy-N-Methyl-N-allyltryptamine  |
| 4-HO-MSBT  | artificial  | 4-OH  | CH(CH3)CH2CH3 | CH3 | 4-hydroxy-N-sec-butyl-N-methyltryptamine  |
| 4-HO-EiBT | artificial[8] | 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
| 4-HO-McPeT | artificial  | 4-OH  | C5H9 | CH3 | 4-hydroxy-N-cyclopentyl-N-methyltryptamine  | 77872-48-1
| 4-HO-McPMT [9] | 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
| 4-HO-PiPT | artificial  | 4-OH  | CH2CH2CH3 | CH(CH3)2 | 4-hydroxy-N-propyl-N-isopropyltryptamine  |
| 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-Acetoxy-DiPT | artificial  | 4-OCOCH3 | CH(CH3)2 | CH(CH3)2 | 4-acetoxy-N,N-diisopropyltryptamine  | 936015-60-0
| 4-PrO-DiPT  | artificial  | 4-OCOCH2CH3 | CH(CH3)2 | CH(CH3)2 | 4-propionyloxy-N,N-diisopropyltryptamine  | 1373882-13-3
| 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
| 4-HO-DALT  | artificial  | 4-OH  | H2C=CH-CH2 | H2C=CH-CH2 | 4-hydroxy-N,N-diallyltryptamine  |
| 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
| 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
| 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
| 5-MeO-MPT  | artificial  | 5-OCH3 | CH3 | CH2CH2CH3 | 5-methoxy-N-methyl-N-propyltryptamine  |
| 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
| 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
| 5-MeO-ALiPT  | 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  |
| 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  |
| 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
| 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 | artificial  | 5-OCOCH3 | CH3 | CH3 | 5-acetoxy-N,N-dimethyltryptamine  | 16977-50-7
| 5-AcO-MET [10] | 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 [11] | 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
| 5-HO-DET  | artificial  | 5-OH  | CH2CH3 | CH2CH3 | 5-hydroxy-N,N-diethyltryptamine  | 14009-42-8
| 5-HO-DPT  | artificial  | 5-OH  | CH2CH2CH3 | CH2CH2CH3 | 5-hydroxy-N,N-dipropyltryptamine  | 36288-75-2
| 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
| 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 [12] | artificial | 5-C(CH3)3 | CH3 | CH3 | 5-(tert-butyl)-N,N-dimethyltryptamine |
| 5-Fluoro-DMT | artificial | 5-F | CH3 | CH3 | 5-fluoro-N,N-dimethyltryptamine | 22120-36-1
| 5-Fluoro-MET | artificial | 5-F | CH3 | CH2CH3 | 5-fluoro-N-methyl-N-ethyltryptamine |
| 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
| 5-Iodo-DMT | artificial | 5-I | CH3 | CH3 | 5-iodo-N,N-dimethyltryptamine | 22120-38-3
| 5-TFM-DMT | artificial | 5-CF3 | CH3 | CH3 | 5-(trifluoromethyl)-N,N-dimethyltryptamine | 2418713-32-1
| 5-TFMO-DMT[13] | artificial | 5-OCF3 | CH3 | CH3 | 5-(trifluoromethoxy)-N,N-dimethyltryptamine |
| 5-Nitro-DMT[14] | 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
| 6-Fluoro-DMT | artificial | 6-F | CH3 | CH3 | 6-fluoro-N,N-dimethyltryptamine | 1511-31-5
| 6-Fluoro-DET[15] | 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
| 6-Methyl-DMT | artificial | 6-CH3 | CH3 | CH3 | 6,N,N-trimethyltryptamine |
| 6-Hydroxy-DMT | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-dimethyltryptamine | 1476-33-1
| 6-Hydroxy-DET | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-diethyltryptamine | 1476-59-1
| 6-Methoxy-DMT | artificial | 6-OCH3 | CH3 | CH3 | 6-methoxy-N,N-dimethyltryptamine | 2426-88-2
| 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[16] | artificial | 7-Br | CH3 | CH3 | 7-bromo-N,N-dimethyltryptamine | 74798-68-8
| 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
| 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
| NB-5-MeO-MiPT  | artificial  | 1-OCOC(CH3)3, 5-OCH3 | CH3 | CH(CH3)2 | 1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine  |
| 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  |
| 6-Fluoropsilocin | artificial | 4-OH,6-F | CH3 | CH3 | 4-hydroxy-6-fluoro-N,N-dimethyltryptamine | 312314-12-8
| 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
| 5-Methoxy-7,N,N-trimethyltryptamine | artificial  | 5-OCH3, 7-CH3 | CH3 | CH3 | 5-Methoxy-7,N,N-trimethyltryptamine  | 61018-77-7
| 5-Methoxy-4,N,N-trimethyltryptamine  | artificial  | 4-CH3, 5-OCH3 | CH3 | CH3 | 5-Methoxy-4,N,N-trimethyltryptamine  |
| 4-HO-5-MeO-DMT | artificial  | 4-OH, 5-OCH3 | CH3 | CH3 | 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine  | 2433-31-0
| 4-F-5-MeO-DMT | artificial  | 4-F, 5-OCH3 | CH3 | CH3 | 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine  | 312314-18-4
| 5-methoxy-7-fluoro-MET  | artificial  | 5-OCH3, 7-F  | CH3 | CH2CH3 | 5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine  |
| EMDT | artificial  | 2-CH2CH3, 5-OCH3 | CH3 | CH3 | 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine  | 263744-72-5
| ST-1936 | artificial  | 2-CH3, 5-Cl  | CH3 | CH3 | 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine  | 1210-81-7
| O-4310 | 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
| CP-132,484 | 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[17] | 4,5-(CH2CH2O)  | CH3 | CH3 | 2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine  |
| 4,5-Methylbenzodioxole-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  |
Chemical Structure  | Short Name  | Origin  | Ring Substitution  | RN1 | RN2 | Full Name  | CAS Number

## 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.[18][19][20] 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.[20] This is analogous to α-methylation of phenethylamine into amphetamine.[20]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[21][22][23][24] and produce psychostimulant, entactogen, and/or psychedelic effects.[18][19][20] The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs.[19][20] In accordance with its action as a dual releasing agent of serotonin and dopamine, αET 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 αMT, 5-MeO-αMT, and various others.[25]

Structure  | Common name  | Chemical name  | CAS number

|
|
|

| Tryptophan | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid  | 73-22-3
| 5-Hydroxytryptophan | 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid  | 4350-09-8
| αMT | 1-(1H-Indol-3-yl)propan-2-amine  | 299-26-3
| 4-HO-αMT | 3-(2-aminopropyl)-1H-indol-4-ol  | 15066-09-8
| 4-Methyl-αMT | 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine  | 3569-29-7
| 5-Fluoro-αMT  | 1-(5-fluoro-1H-indol-3-yl)propan-2-amine  | 712-08-3
| 5-Chloro-αMT | 1-(5-Chloro-1H-indol-3-yl)propan-2-amine  | 712-07-2
| 5-HO-αMT (αMS/α-methyl-5-HT)  | 3-(2-aminopropyl)-1H-indol-5-ol  | 304-52-9
| 5-MeO-αMT  | 1-(5-methoxy-1H-indol-3-yl)propan-2-amine  | 1137-04-8
| 5-Ethoxy-αMT | 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine  | 101832-83-1
| 5-Isopropoxy-αMT  | 1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine  |
| BW-723C86 | 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine  | 160521-72-2
| 6-Fluoro-αMT  | 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-dihydropyrano-αMT)  | (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole  | 362603-40-5
| Compound 5 [26] | 1-(3H-benzo[e]indol-1-yl)propan-2-amine  |
| αET | 1-(1H-indol-3-yl)butan-2-amine  | 2235-90-7
| 4-Methyl-αET  | 1-(4-Methyl-1H-indol-3-yl)butan-2-amine  | 28289-30-7
| 4-HO-αET  | 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine  | 28289-28-3
| 5-Fluoro-αET  | 1-(5-fluoro-1H-indol-3-yl)butan-2-amine  | 1380137-98-3
| 5-Methyl-αET  | 1-(5-methyl-1H-indol-3-yl)butan-2-amine  | 1380148-21-9
| 5-MeO-αET  | 1-(5-methoxy-1H-indol-3-yl)butan-2-amine  | 4765-10-0
| 7-Methyl-αET  | 1-(7-methyl-1H-indol-3-yl)butan-2-amine  | 13712-80-6
| N-Methyl-5-MeO-αMT (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
| N,N-Dimethyl-αMT (α,N,N-TMT)  | (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine  | 4761-32-4
| N,N-Dimethyl-5-MeO-αMT (5-MeO-α,N,N-TMT)  | (2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine  | 101831-90-7
| αMDiPT  | (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine  |
| MPMI[27] | 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole  | 143321-54-4
| Lucigenol  | (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole  | 250672-65-2
| 5-MeO-MPMI | 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole  | 143321-57-7
| 5F-MPMI[28] | (R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole  |
| 5-Br-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
| Z5247692566[4][29] | 4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine  |

## Related compounds

A number of related compounds are known, with a similar structure but having the indole core flipped and/or replaced with related cores such as indoline, indazole, benzothiophene, or benzofuran. These similarly 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.

Structure  | Common name  | Chemical name  | CAS number

|
|
|

| Dimemebfe | 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine  | 140853-58-3
| 5-MeO-DiBF | N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine  |
| 3-APB  | 3-(2-aminopropyl)benzofuran  | 105909-13-5
| Mebfap  | 3-(2-aminopropyl)-5-methoxybenzofuran  | 140853-59-4
| Ro60-0175 | (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine  | 169675-09-6
| AAZ-A-154 | (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine  |
| Example 1 [30] | 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 | 1-((S)-2-Aminopropyl)-1H-indazol-6-ol  | 210580-75-9
| O-methyl-AL-34662  | 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole  | 210580-60-2
| 7-methyl-AL-34662  | 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol  | 874668-67-4
| 7-chloro-AL-34662  | 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol  | 874881-86-4
| AL-38022A | (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine  | 478132-11-5
| Example 9 [31] | (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine  | 478132-12-6
| Example 3 [32] | (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine  | 890087-75-9
| Example 1 [33] | (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 [34] | (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine  | 748116-94-1
| I-32 [35] | 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol  |
| 2-Azapsilocin (Psilocin indazole analogue, P-6)[36] | 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol  |
| 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  |
| (R)-69 | 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine  |
| SN-22 | 3-(1-methylpiperidin-4-yl)-1H-indole  | 17403-07-5

## Further reading

* TiHKAL

## See also

* Ergoline
* Lysergamide
* Iboga alkaloid
* Substituted amphetamine
* Substituted benzofuran
* Substituted cathinone
* Substituted methylenedioxyphenethylamine
* Substituted phenethylamine
* 2C, DOx, 25-NB
* List of miscellaneous 5HT2A agonists

## 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. ↑ "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE 14 (1): e0209804. 2019. doi:10.1371/journal.pone.0209804. PMID 30629611. Bibcode: 2019PLoSO..1409804T.
3. ↑ Jensen N. Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. PhD thesis, University of Göttingen, 2004
4. ↑ 4.0 4.1 "AlphaFold2 structures template ligand discovery". bioRxiv. December 2023. doi:10.1101/2023.12.20.572662. PMID 38187536.
5. ↑ "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.
6. ↑ "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.
7. ↑ "Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug". Acta Crystallographica. Section E, Crystallographic Communications 77 (Pt 2): 101–106. February 2021. doi:10.1107/S2056989021000116. PMID 33614134.
8. ↑ Banister S, Jorgensen W, Jinlong T, "Compounds", WO patent 2023115167, published 29 June 2023
9. ↑ 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.
10. ↑ Stamets PE, "Tryptamine Compositions for Enhancing Neurite Outgrowth.", WO patent 2021101926, published 2021-05-27, assigned to Stamets Paul Edward.
11. ↑ Kruegel AC, Sporn J, "Specific Tryptamines for use in the Treatment of Mood Disorders.", WO patent 2021168082, published 26 August 2021
12. ↑ "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.
13. ↑ Kruegel AC, "Novel Tryptamines and Methods of Treating Mood Disorders", WO patent 2022235927, published 10 November 2022, assigned to Gilgamesh Pharmaceuticals, Inc.
14. ↑ "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.
15. ↑ "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.
16. ↑ "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry 23 (11): 1222–6. November 1980. doi:10.1021/jm00185a014. PMID 6779006.
17. ↑ Banister S, Jorgensen W, Jinlong T, "Compounds", WO patent 2023115166, published 29 June 2023
18. ↑ 18.0 18.1 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.
19. ↑ 19.0 19.1 19.2 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.
20. ↑ 20.0 20.1 20.2 20.3 20.4 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.
21. ↑ "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.
22. ↑ "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.
23. ↑ "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.
24. ↑ "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.
25. ↑ "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.
26. ↑ "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.
27. ↑ Macor JE, Wythes MJ, "Indole derivatives", US patent 5607951, issued 4 March 1997, assigned to Pfizer, Inc.
28. ↑ 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.
29. ↑ "AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery?". Nature News. 18 January 2024. doi:10.1038/d41586-024-00130-8.
30. ↑ Chen HH, May JA, "Pyranoindoles for treating glaucoma", US patent granted 7012090, published 17 March 2000, issued 14 March 2006, assigned to Alcon, Inc.
31. ↑ 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.
32. ↑ 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.
33. ↑ "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.
34. ↑ "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.
35. ↑ 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
36. ↑ Banister S, Jorgensen W, Jinlong T, "Compounds", WO patent 2023115165, published 29 June 2023

* 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

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

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

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