Tryptamine



Tryptamine
IUPAC name 2-(1H-indol-3-yl)ethanamine
Identifiers
CAS number 61-54-1
PubChem 1150
SMILES C1=CC=C2C(=C1)C(=CN2)CCN
Properties
Molecular formula C10H12N2
Molar mass 160.216
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Tryptamine is a neurotransmitter.[1]

Tryptamine is also the backbone for a group of compounds known collectively as tryptamines. This group includes many neurotransmitters and hallucinogens.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.[2]

Plants containing tryptamine

Many if not most plants contain small amounts of tryptamine which is an intermediate in one Acacia species.

Tryptamine acts as a natural pesticide in plants.[4]

Tryptamine derivatives

The most well-known tryptamines are sumatriptan and its relatives. The tables below list some commonly encountered substituted tryptamines.

 

The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: yohimbine.

A thorough investigation of dozens of tryptamine compounds was published by Ann and TiHKAL.

Naturally occurring tryptamines (see also Table of naturally occurring tryptamines)
Short Name Rα R4 R5 R6 RN1 RN2 Full Name
Bufotenin H H OH H CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
DMT H H H H CH3 CH3 N,N-dimethyltryptamine
Melatonin H H OCH3 H O=CH-CH3 H 5-methoxy-N-acetyltryptamine
5-MeO-DMT H H OCH3 H CH3 CH3 5-methoxy-N,N-dimethyltryptamine
NMT H H H H H CH3 N-methyltryptamine
Psilocybin H PO4 H H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
Psilocin H OH H H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
Serotonin H H OH H H H 5-hydroxytryptamine
COOH H H H H H α-carboxyltryptamine
Synthetic tryptamines
Short Name Rα R4 R5 RN1 RN2 Full Name
AET CH2CH3 H H H H α-ethyltryptamine
AMT CH3 H H H H α-methyltryptamine
DET H H H CH2CH3 CH2CH3 N,N-diethyltryptamine
DiPT H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
DPT H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
5-MeO-AMT CH3 H OCH3 H H 5-methoxy-α-methyltryptamine
4-HO-DET H OH H CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine
4-HO-DIPT H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT H H OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine
4-HO-MiPT H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
Sumatriptan H H SO2NHCH3 CH3 CH3 5-methylaminosulfonyl-N,N-dimethyltryptamine
5-DAT H OCH3 H O=CH-CH3 O=CH-CH3 5-methoxy-N,N-diacetyltryptamine
HPT H H OCH3 H C9H13NO2 5-methyloxy-N-demethylhydroxyephedryltryptamine

The Abramovitch-Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamines starting from a beta-Carboline [5]

References

  1. ^ Jones R.S. (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in neurobiology 19: 117–139.
  2. ^ Effects of tryptamine mediated through 2 states of the 5-HT ...
  3. ^ Takahashi, Dean Nobutaka, Chemistry of Plant Hormones, CRC Press
  4. ^ Dr. Duke's Phytochemical and Ethnobotanical Databases -- Biological Activities of TRYPTAMINE
  5. ^ 880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and -carbolines R. A. Abramovitch and D. Shapiro J. Chem. Soc., 1956, 4589 - 4592, doi:10.1039/JR9560004589

See also


v • d • e
Psychedelic tryptamines

α,N,N-TMT • 2,N,N-TMT • 5,N,N-TMT • 4-Acetoxy-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-HO-5-MeO-DMT • α-ET • α-MT • Baeocystin • Bufotenin • DBT • DET • DIPT • DMT • DPT • EiPT • PiPT • Ethocin • Ethocybin • Iprocin • 4-HO-MET • 4-HO-MiPT • MET • MIPT • 5-Me-MIPT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MET • 5-MeO-MIPT • 5-MeO-α,N,N-TMT • 5-MeO-2,N,N-TMT • Miprocin • Norbaeocystin • Psilocin • Psilocybin

v • d • e
Antimigraine preparations (Clonidine • Iprazochrome • Dimetotiazine • Oxetorone
v • d • e
Tryptamines

4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-DIPT • 5-Bromo-DMT • 5-Fluoro-α-MT • 5-MeO-α-ET  • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • α-ET • α-MT • Baeocystin • Bufotenin • DET • DiPT • DMT • DPT • Ethocybin • EiPT • Ethocin • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • NMT • Norbaeocystin • Normelatonin • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tryptamine". A list of authors is available in Wikipedia.