Short description: Chemical compound
LAMPA |
| Clinical data |
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| Other names | LMP |
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| Legal status |
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| Legal status |
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| Identifiers |
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IUPAC name
N,7-dimethyl-N-propyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
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| CAS Number | |
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| PubChem CID | |
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| ChemSpider | |
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| Chemical and physical data |
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| Formula | C20H25N3O |
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| Molar mass | 323.440 g·mol−1 |
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| 3D model (JSmol) | |
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SMILES
CCCN(C)C(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C
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InChI
InChI=InChI=1S/C20H25N3O/c1-4-8-22(2)20(24)14-9-16-15-6-5-7-17-19(15)13(11-21-17)10-18(16)23(3)12-14/h5-7,9,11,14,18,21H,4,8,10,12H2,1-3H3 Key:CZRJGQXHVRNZRZ-UHFFFAOYSA-N
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LAMPA (N-methyl-N-propyl lysergamide) is a structural analogue of lysergic acid diethylamide (LSD) that has been studied as a potential treatment for alcoholism.[1] In animal studies, LAMPA was found to be nearly equipotent to ECPLA and MIPLA for inducing a head-twitch response. LAMPA appears to be significantly less potent than LSD in humans, producing little to no noticeable effects at doses of 100 µg.[2]
See also
References
- ↑ "Comparison of LSD with methysergide and psilocybin on test subjects.". The use of LSD in psychotherapy and alcoholism.. Bobbs-Merrill Company Inc.. 1967. pp. 53–57. https://www.samorini.it/doc1/alt_aut/ad/abramson-the-use-of-lsd-in-psychotherapy-and-alcoholism.pdf. Retrieved 15 May 2022.
- ↑ "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology 236 (2): 799–808. February 2019. doi:10.1007/s00213-018-5055-9. PMID 30298278.
Hallucinogens |
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Psychedelics (5-HT2A agonists) | | Benzofurans |
- 2C-B-FLY
- 2CBFly-NBOMe
- 5-MeO-BFE
- 5-MeO-DiBF
- Bromo-DragonFLY
- F-2
- F-22
- TFMFly
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Lyserg‐ amides |
- 1B-LSD
- 1P-ETH-LAD
- 1P-LSD
- 2-Butyllysergamide
- 3-Pentyllysergamide
- AL-LAD
- ALD-52
- BU-LAD
- Diallyllysergamide
- Dimethyllysergamide
- ECPLA
- Ergometrine
- ETH-LAD
- IP-LAD
- LAE-32
- LAMPA
- LPD-824
- LSA
- LSD
- LSD-Pip
- LSH
- LSM-775
- LSZ
- Methylergometrine
- MIPLA
- Methysergide
- MLD-41
- PARGY-LAD
- PRO-LAD
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Phenethyl‐ amines | |
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| Piperazines | |
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| Tryptamines | | alpha-alkyltryptamines |
- 4,5-DHP-α-MT
- 5-MeO-α-ET
- 5-MeO-α-MT
- α-ET
- α-MT
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| x-DALT |
- (Daltocin) 4-HO-DALT
- (Daltacetin) 4-AcO-DALT
- 5-MeO-DALT
- DALT
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| x-DET |
- (Ethacetin) 4-AcO-DET
- (Ethocin) 4-HO-DET
- 5-MeO-DET
- (T-9) DET
- (Ethocybin) 4-PO-DET
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| x-DiPT |
- (Ipracetin) 4-AcO-DiPT
- (Iprocin) 4-HO-DiPT
- 5-MeO-DiPT
- DiPT
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| x-DMT |
- 4,5-DHP-DMT
- 2,N,N-TMT
- 4-AcO-DMT
- 4-HO-5-MeO-DMT
- 4,N,N-TMT
- 4-Propionyloxy-DMT
- 5,6-diBr-DMT
- 5-AcO-DMT
- 5-Bromo-DMT
- 5-MeO-2,N,N-TMT
- 5-MeO-4,N,N-TMT
- 5-MeO-α,N,N-TMT
- 5-MeO-DMT
- 5-N,N-TMT
- 7,N,N-TMT
- α,N,N-TMT
- (Bufotenin) 5-HO-DMT
- DMT
- Norbaeocystin
- (Psilocin) 4-HO-DMT
- (Psilocybin) 4-PO-DMT
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| x-DPT |
- (Depracetin) 4-AcO-DPT
- (Deprocin) 4-HO-DPT
- 5-MeO-DPT
- (The Light) DPT
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| Ibogaine-related |
- 18-MAC
- 18-MC
- Coronaridine
- Ibogaine
- Ibogamine
- ME-18-MC
- Noribogaine
- Tabernanthine
- Voacangine
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| x-MET |
- (Metocin) 4-HO-MET
- (Metocetin) 4-AcO-MET
- 5-MeO-MET
- MET
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| x-MiPT |
- (Mipracetin) 4-AcO-MiPT
- (Miprocin) 4-HO-MiPT
- 5-Me-MiPT
- (Moxy) 5-MeO-MiPT
- MiPT
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| Others |
- 4-HO-DBT
- 4-HO-EPT
- 4-HO-McPT
- (Lucigenol) 4-HO-MPMI
- (Meprocin) 4-HO-MPT
- 5-MeO-EiPT
- 5-MeO-MALT
- 5-MeO-MPMI
- Aeruginascin
- Baeocystin
- DBT
- DCPT
- EiPT
- EPT
- MPT
- PiPT
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| Others |
- AL-38022A
- ALPHA
- Dimemebfe
- Efavirenz
- Lorcaserin
- M-ALPHA
- RH-34
Also empathogens in general (e. g.: 5-APB, 5-MAPB]], 6-APB and other substituted benzofurans, Chemistry:MDAI
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Dissociatives (NMDAR antagonists) | Arylcyclo‐ hexylamines | | Ketamine-related |
- 2-Fluorodeschloroketamine
- Arketamine ((R)-ketamine)
- Deschloroketamine
- Ethketamine (N-Ethylnorketamine)
- Esketamine ((S)-ketamine)
- Ketamine
- Methoxetamine
- Methoxmetamine
- Methoxyketamine
- Norketamine
- Tiletamine
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| PCP-related |
- 3'-HO-PCP
- 3'-MeO-PCE
- 3'-MeO-PCMo
- 3'-MeO-PCP
- BDPC
- Dieticyclidine (PCDE)
- Eticyclidine (PCE)
- Methoxydine (4'-MeO-PCP)
- PCPr
- Phencyclidine (PCP)
- Rolicyclidine (PCPy)
- Tenocyclidine (TCP)
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| Others | |
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| Diarylethylamines |
- Diphenidine
- Ephenidine
- Fluorolintane
- Methoxphenidine
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| Morphinans |
- Dextrallorphan
- Dextromethorphan
- Dextrorphan
- Racemethorphan
- Racemorphan
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| Others |
- 2-EMSB
- 2-MDP
- 8A-PDHQ
- Aptiganel
- Budipine
- Delucemine
- Dexoxadrol
- Dizocilpine
- Etoxadrol
- Herkinorin
- Ibogaine
- Midafotel
- NEFA
- Neramexane
- Nitrous oxide
- Noribogaine
- Perzinfotel
- RB-64
- Remacemide
- Salvinorin A
- Selfotel
- Xenon
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Deliriants (mAChR antagonists) |
- Atropine
- Benactyzine
- Benzatropine
- Benzydamine
- Biperiden
- BRN-1484501
- Brompheniramine
- BZ
- CAR-226,086
- CAR-301,060
- CAR-302,196
- CAR-302,282
- CAR-302,368
- CAR-302,537
- CAR-302,668
- Chloropyramine
- Chlorphenamine
- Clemastine
- CS-27349
- Cyclizine
- Cyproheptadine
- Dicycloverine
- Dimenhydrinate
- Diphenhydramine
- Ditran
- Doxylamine
- EA-3167
- EA-3443
- EA-3580
- EA-3834
- Elemicin
- Flavoxate
- Hyoscyamine
- JB-318
- JB-336
- Meclozine
- Mepyramine
- Myristicin
- Orphenadrine
- Oxybutynin
- Pheniramine
- Phenyltoloxamine
- Procyclidine
- Promethazine
- Scopolamine
- Tolterodine
- Trihexyphenidyl
- Tripelennamine
- Triprolidine
- WIN-2299
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| Others | Cannabinoids (CB1 agonists) | |
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| D2 agonists |
- Apomorphine
- Aporphine
- Bromocriptine
- Cabergoline
- Lisuride
- Memantine
- Nuciferine
- Pergolide
- Phenethylamine
- Piribedil
- Pramipexole
- Ropinirole
- Rotigotine
- Salvinorin A
Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).
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GABAA enhancers |
- CI-966
- Eszopiclone
- Ibotenic acid
- Muscimol (Amanita muscaria)
- Zaleplon
- Zolpidem
- Zopiclone
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Inhalants (Mixed MOA) |
- Aliphatic hydrocarbons
- Butane
- Gasoline
- Kerosene
- Propane
- Aromatic hydrocarbons
- Ethers
- Haloalkanes
- Chlorofluorocarbons
- Chloroform
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| κOR agonists |
- 2-EMSB
- Alazocine
- Bremazocine
- Butorphan
- Butorphanol
- Cyclazocine
- Cyclorphan
- Cyprenorphine
- Diprenorphine
- Enadoline
- Herkinorin
- Heroin
- HZ-2
- Ibogaine
- Ketazocine
- Levallorphan
- Levomethorphan
- Levorphanol
- LPK-26
- Metazocine
- Morphine
- Nalbuphine
- Nalmefene
- Nalorphine
- Noribogaine
- Oxilorphan
- Pentazocine
- Phenazocine
- Proxorphan
- Racemethorphan
- Racemorphan
- Salvinorin A
- Spiradoline
- Tifluadom
- U-50488
- U-69,593
- Xorphanol
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| Others |
- Glaucine
- Isoaminile
- Noscapine
- Pukateine
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Ergolines |
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Lysergic acid derivatives |
- 2-Bromo-LSD (BOL-148)
- Bromocriptine
- Cabergoline
- Dihydroergocornine
- Dihydroergocristine
- Dihydroergocryptine
- Dihydroergometrine (Dihydroergonovine, Dihydroergobasine)
- Dihydroergosine
- Dihydroergotamine
- Epicriptine
- Ergine (LSA; LA-111; Lysergamide)
- Ergocornine
- Ergocristine
- Ergocryptine
- Ergoloid (Dihydroergotoxine)
- Ergometrine (Ergonovine, Ergobasine)
- Ergometrinine
- Ergotamine
- Ergotoxine
- Ergovaline
- Lisuride
- LSD
- LSH
- Lysergic Acid
- Lysergic acid cyclobutylamide
- Lysergic acid cyclopentylamide
- Lysergic Acid Methyl Ester
- Lysergol
- Mesulergine
- Metergoline
- Methergine (Methylergometrine, Methylergonovine, Methylergobasine)
- Methysergide
- Pergolide
- Syntometrine
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Psychedelic lysergamides |
- 1B-LSD
- 1P-ETH-LAD
- 1P-LSD
- AL-LAD
- ALD-52
- BU-LAD
- CYP-LAD
- DAL
- DAM-57
- ECPLA
- Ergonovine
- ETFELA
- ETH-LAD
- IP-LAD
- LAMPA
- LAE-32
- LSD
- LPD-824
- LSM-775
- LSH
- LSD-Pip
- Lysergic Acid 2-Butylamide
- Lysergic Acid 2,4-Dimethylazetidide
- Lysergic Acid 3-Pentylamide
- Methylergonovine
- MIPLA
- MLD-41
- PARGY-LAD
- PRO-LAD
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| clavines |
- agroclavine
- elymoclavine
- lysergol
- festuclavine
- fumigaclavine A
- fumigaclavine B
- fumigaclavine C
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Other ergolines | |
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Natural sources |
- Achnatherum robustum (Sleepy Grass)
- Claviceps spp. (Ergot)
Morning glory: Argyreia nervosa (Hawaiian Baby Woodrose), Ipomoea spp.(Morning Glory, Tlitliltzin, Badoh Negro), Rivea corymbosa (Coaxihuitl, Ololiúqui)
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 | Original source: https://en.wikipedia.org/wiki/LAMPA. Read more |