Tryptamines

General structural formula of tryptamines

Tryptamines are chemical compounds that are derived from 2- (indol-3-yl) -ethylamine . They are metabolic products of numerous living things (especially plants) and count among the indole alkaloids . Prominent derivatives with tryptamine structure are the neurotransmitters serotonin and melatonin , the amino acid tryptophan and the psychedelic effective hallucinogens dimethyltryptamine and psilocybin and psilocin .

Table overview

Substituted tryptamines , listed by structure

Surname	R 4	R 5	R α	R N 1	R N 2	chemical name	origin
Tryptamine	H	H	H	H	H	2- (indol-3-yl) ethylamine	Naturally
NMT	H	H	H	H	CH 3	N -methyltryptamine	Naturally
5-MeO-NMT	H	OCH 3	H	H	CH 3	5- methoxy - N -methyltryptamine	Naturally
Dimethyltryptamine	H	H	H	CH 3	CH 3	N , N -di methyl tryptamine	Naturally
5-MeO-DMT	H	OCH 3	H	CH 3	CH 3	5- methoxy - N , N -di methyl tryptamine	Naturally
5-bromo DMT	H	Br	H	CH 3	CH 3	5-bromo- N , N -di methyl tryptamine	Naturally
Bufotenin	H	OH	H	CH 3	CH 3	5- hydroxy - N , N -di methyl tryptamine	Naturally
N -methyl serotonin	H	OH	H	CH 3	H	5- hydroxy - N -methyltryptamine	Naturally
Serotonin	H	OH	H	H	H	5- hydroxy tryptamine	Naturally
Psilocin	OH	H	H	CH 3	CH 3	4- hydroxy - N , N -di methyl tryptamine	Naturally
Psilocybin	OPO 3 H 2	H	H	CH 3	CH 3	4-Phosphoryloxy- N , N -di methyl tryptamine	Naturally
Baeocystin	OPO 3 H 2	H	H	CH 3	H	4-phosphoryloxy- N - methyl tryptamine	Naturally
Norbaeocystin	OPO 3 H 2	H	H	H	H	4-phosphoryloxytryptamine	Naturally
Melatonin	H	OCH 3	H	O = CH-CH 3	H	5 - methoxy - N - acetyl tryptamine	Naturally
Tryptophan	H	H	COOH	H	H	α- carboxy- tryptamine	Naturally
Surname	R 4	R 5	R α	R N 1	R N 2	chemical name	origin
AMT	H	H	CH 3	H	H	α- methyl tryptamine	synthetic
5-MeO-AMT	H	OCH 3	CH 3	H	H	5- methoxy- α- methyl tryptamine	synthetic
AET	H	H	CH 2 CH 3	H	H	α- ethyl tryptamine	synthetic
NET	H	H	H	H	CH 2 CH 3	N - ethyl tryptamine	synthetic
DET	H	H	H	CH 2 CH 3	CH 2 CH 3	N , N -di ethyl tryptamine	synthetic
DiPT	H	H	H	CH (CH 3 ) 2	CH (CH 3 ) 2	N , N -di -isopropyl tryptamine	synthetic
DPT	H	H	H	CH 2 CH 2 CH 3	CH 2 CH 2 CH 3	N , N -di propyl tryptamine	synthetic
DBT	H	H	H	CH 2 CH 2 CH 2 CH 3	CH 2 CH 2 CH 2 CH 3	N , N -di butyl tryptamine	synthetic
4-HO-MET	OH	H	H	CH 3	CH 2 CH 3	4- hydroxy - N - methyl - N - ethyl tryptamine	synthetic
4-HO-DET	OH	H	H	CH 2 CH 3	CH 2 CH 3	4- hydroxy - N , N -di ethyl tryptamine	synthetic
4-PO-DET	OPO 3 H 2	H	H	CH 2 CH 3	CH 2 CH 3	4-phosphoryloxy- N , N -di ethyl tryptamine	synthetic
4-HO-DIPT	OH	H	H	CH (CH 3 ) 2	CH (CH 3 ) 2	4- hydroxy - N , N -di -isopropyl tryptamine	synthetic
4-HO-MiPT	OH	H	H	CH (CH 3 ) 2	CH 3	4- hydroxy - N - isopropyl - N - methyl tryptamine	synthetic
5-MeO-DALT	H	OCH 3	H	H 2 C = CH-CH 2	H 2 C = CH-CH 2	5- methoxy - N , N -di allyl tryptamine	synthetic
5-MeO-DiPT	H	OCH 3	H	CH (CH 3 ) 2	CH (CH 3 ) 2	5- methoxy - N , N -di -isopropyl tryptamine	synthetic
Sumatriptan	H	CH 2 SO 2 NHCH 3	H	CH 3	CH 3	5-methylaminosulfonyl N , N -di methyl tryptamine	synthetic

synthesis

Tryptamine can be made by the Abramovitch – Shapiro synthesis process.

Graphic overview

Overview of a small selection of endogenous, natural and synthetic tryptamines:

See also

• Phenylethylamines

literature

• Alexander Shulgin , Ann Shulgin: TiHKAL, the Continuation . Transform Press, Berkeley 1997, ISBN 0-9630096-9-9 .
• Keeper of the Trout & Friends: Some Simple Tryptamines (Second Edition) . Mydriatic Productions, 2007, ISBN 9780977087655 .
• Ana Margarida Araújo, Félix Carvalho u. a .: The hallucinogenic world of tryptamines: an updated review. In: Archives of Toxicology. 89, 2015, p. 1151, doi : 10.1007 / s00204-015-1513-x .

Individual evidence

1. ↑ Abramovitch RA, Shapiro D.: 880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and β-carbolines. In: Journal of the Chemical Society (Resumed). 1956, p. 4589, doi : 10.1039 / JR9560004589 .