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style="background: #F8EABA; text-align: center;" colspan="2" Tryptamine
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200px
Identifiers
CAS number 61-54-1
PubChem 1150
SMILES C1=CC=C2C(=C1)C(=CN2)CCN
Properties
Molecular formula C10H12N2
Molar mass 160.216
Hazards
style="background: #F8EABA; text-align: center;" colspan="2" 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]

Plants containing tryptamineEdit

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 derivativesEdit

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.

Tryptamine rests

General structure of 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.

The tryptamine structure, in particular its indole ring, may be 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.


Selected Tryptamines (see also Table of naturally occurring tryptamines)
Short Name Origin Rα R4 R5 RN1 RN2 Full Name
TryptamineNatural H H H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
BufoteninNatural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
Nω-methylserotonin (norbufotenin)Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine
SerotoninNatural H H OH H H 5-hydroxytryptamine
DMTNatural H H H CH3 CH3 N,N-dimethyltryptamine
MelatoninNatural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine
5-Bromo-DMTNatural H H Br CH3 CH3 5-bromo-N,N-dimethyltryptamine
5-MeO-DMTNatural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
5-MeO-NMTNatural H H OCH3 CH3 H 5-methoxy-N-methyltryptamine
NMTNatural H H H H CH3 N-methyltryptamine
NorbaeocystinNatural H OPO3H2 H H H 4-phosphoryloxy-tryptamine
BaeocystinNatural H OPO3H2 H CH3 H 4-phosphoryloxy-N-methyl-tryptamine
PsilocybinNatural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
PsilocinNatural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
TryptophanNatural 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

Synthesis Edit

The Abramovitch–Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamines starting from a β-carboline.[5]

See also Edit

ReferencesEdit

  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. (1956). 880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and ?-carbolines. Journal of the Chemical Society (Resumed): 4589.


External links Edit




Tryptamines edit
4-Acetoxy-DET | 4-Acetoxy-DIPT | 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 | EIPT | Ethocin | Ibogaine | Iprocin | MET | MIPT | Miprocin | Melatonin | NMT | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan
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