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
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
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
- ↑ 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 .