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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 monoamine alkaloid found in plants and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.[1]

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

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

Contents

Plants containing tryptamine

Many if not most plants contain small amounts of tryptamine which is an intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid (heteroauxin).[3] Higher concentrations can be found in many Acacia species.

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

Tryptamine derivatives

The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are commonly used by humans for their psychotropic effects. Prominent examples include psilocybin (from "magic mushrooms") and DMT (from numerous plant sources, e.g. chacruna, often used in ayahuasca brews). Many synthetic tryptamines have also been made, including the migraine drug 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: LSD, ibogaine and yohimbine.

A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title 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
Tryptophan 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 (N02C)
Ergot alkaloidsDihydroergotamine • Ergotamine • Methysergide • Lisuride
Corticosteroid derivativesFlumedroxone
Selective serotonin (5-HT1) agonistsTriptans (Almotriptan, Eletriptan, Frovatriptan, Naratriptan, Rizatriptan, Sumatriptan, Zolmitriptan)
Other antimigraine preparationsPizotifen • 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.
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