Warning
This is an unofficial archive of PsychonautWiki as of 2025-08-11T15:14:44Z. Content on this page may be outdated, incomplete, or inaccurate. Please refer to the original page for the most up-to-date information.

Category:Tryptamine

From PsychonautWiki Archive
Revision as of 05:25, 18 August 2014 by >PJosepherum
(diff) ← Older revision | Latest revision (diff) | Newer revision → (diff)
Jump to navigation Jump to search
Substitutive structure of a tryptamine molecule.

Tryptamine is a mono-amine alkaloid found in animals, plants and fungi.

Substituted tryptamine refers to a class of compounds which typically produce strong psychedelic effects.

Chemistry

Tryptamine comprises an indole ring attached to a mono-amine chain. Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, efficacy and half-life.

Tryptamines, tabulated by structure
Short Name Origin Rα R4 R5 RN1 RN2 Full Name
Tryptamine Natural H H H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
Bufotenin Natural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
Nω-methylserotonin (norbufotenin) Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine
Serotonin Natural H H OH H H 5-hydroxytryptamine
DMT Natural H H H CH3 CH3 N,N-dimethyltryptamine
Melatonin Natural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine
5-Bromo-DMT Natural H H Br CH3 CH3 5-bromo-N,N-dimethyltryptamine
5-MeO-DMT Natural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
5-MeO-NMT Natural H H OCH3 CH3 H 5-methoxy-N-methyltryptamine
NMT Natural H H H H CH3 N-methyltryptamine
Norbaeocystin Natural H OPO3H2 H H H 4-phosphoryloxy-tryptamine
Baeocystin Natural H OPO3H2 H CH3 H 4-phosphoryloxy-N-methyl-tryptamine
Psilocybin Natural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
Psilocin Natural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
Tryptophan Natural COOH H H H H α-carboxyltryptamine
αET Artificial CH2CH3 H H H H α-ethyltryptamine
αMT Artificial CH3 H H H H α-methyltryptamine
DALT Artificial H H H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine
DET Artificial H H H CH2CH3 CH2CH3 N,N-diethyltryptamine
DiPT Artificial H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
DPT Artificial H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
5-MeO-αMT Artificial CH3 H OCH3 H H 5-methoxy-α-methyltryptamine
5-MeO-DALT Artificial H H OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine
4-HO-DET Artificial H OH H CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine
4-AcO-DMT Artificial H OCOCH3 H CH3 CH3 4-acetoxy-N,N-dimethyltryptamine
4-HO-MET Artificial H OH H CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine
4-HO-DIPT Artificial H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT Artificial H H OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine
4-HO-MiPT Artificial H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
Sumatriptan Artificial H H CH2SO2NHCH3 CH3 CH3 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine
Zolmitriptan Artificial H H -(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine
Short Name Origin Rα R4 R5 RN1 RN2 Full Name

Pharmacology

Tryptamines are believed to produce their psychedelic effect primarily by partial agonism of 5-HT2A receptors.

Several neurotransmitters are derived from tryptamine, such as:

References