Tryptamine

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ImageFile2=Tryptamine-3d-sticks.pngIUPACName=2-(1H-indol-3-yl)ethanamine
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CASNo=61-54-1
PubChem=1150
SMILES=C1=CC=C2C(=C1)C(=CN2)CCN
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Formula=C₁₀H₁₂N₂
MolarMass=160.216
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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. [cite journal
author = Jones R.S.
year = 1982
title = Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?
journal = Progress in neurobiology
volume = 19
number = 1–2
pages = 117–139
doi = 10.1016/0301-0082(82)90023-5]

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. [ [http://linkinghub.elsevier.com/retrieve/pii/S0300483X06004100 Effects of tryptamine mediated through 2 states of the 5-HT ...] ]

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). [http://books.google.com/books?id=PQ2nWAPzPcIC&pg=RA3-PA43&lpg=RA3-PA43&dq=acacia+tryptamine+-gum&source=web&ots=zFe1pKHsLM&sig=b8edsYiycL4nsy8sd9rvQti_6CA#PRA3-PA43,M1 Takahashi, Dean Nobutaka, Chemistry of Plant Hormones, CRC Press ] ] Higher concentrations can be found in many Acacia species.

Tryptamine acts as a natural pesticide in plants. [ [http://www.ars-grin.gov/cgi-bin/duke/chem-activities.pl Dr. Duke's Phytochemical and Ethnobotanical Databases -- Biological Activities of TRYPTAMINE] ]

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.

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

References

See also

* Trace amine
* beta-Carboline
* Ergoline
* TiHKAL
* PiHKAL

External links

* [http://www.erowid.org/psychoactives/faqs/faqs_tryptamine.shtml Tryptamine FAQ]
* [http://www.tryptamind.com/tryptamine.html Tryptamine Hallucinogens and Consciousness]
* [http://www.tryptamind.com/ Tryptamind Psychoactives] , reference site on tryptamine and other psychoactives.