Tryptamine

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Tryptamine (3-(2-aminoethyl)indole) is a monoamine compound that is widespread in nature. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds including indole, beta-carboline and ergoline alkaloids and auxins.

Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. 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 table below lists some commonly encountered substituted tryptamines.

The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: ergoline alkaloids like LSD, ibogaine and yohimbine.

A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.

Image:Tryptamine rests.png

Substituted tryptamines, tabulated by structure

Short Name	Rα	R4	R5	RN1	RN2	Full Name
AET	CH2CH3					α-ethyltryptamine
AMT	CH3					α-methyltryptamine
serotonin			OH			5-hydroxytryptamine
DET				CH2CH3	CH2CH3	N,N-diethyltryptamine
DiPT				CH(CH3)2	CH(CH3)2	N,N-diisopropyltryptamine
DMT				CH3	CH3	N,N-dimethyltryptamine
DPT				CH2CH2CH3	CH2CH2CH3	N,N-dipropyltryptamine
melatonin			OCH3	O=CH-CH3		5-methoxy-N-acetyltryptamine
5-MeO-AMT	CH3		OCH3			5-methoxy-α-methyltryptamine
bufotenine			OH	CH3	CH3	5-hydroxy-N,N-dimethyltryptamine
ethocin		OH		CH2CH3	CH2CH3	4-hydroxy-N,N-diethyltryptamine
iprocin		OH		CH(CH3)2	CH(CH3)2	4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT			OCH3	CH(CH3)2	CH(CH3)2	5-methoxy-N,N-diisopropyltryptamine
5-MeO-DMT			OCH3	CH3	CH3	5-methoxy-N,N-dimethyltryptamine
Miprocin		OH		CH(CH3)2	CH3	4-hydroxy-N-isopropyl-N-methyltryptamine
psilocin		OH		CH3	CH3	4-hydroxy-N,N-dimethyltryptamine
psilocybin		OPO3H2		CH3	CH3	4-phosphoryloxy-N,N-dimethyltryptamine
sumatriptan			SO2NHCH3	CH3	CH3	5-methylaminosulfonyl-N,N-dimethyltryptamine

See also

• beta-Carboline
• Ergoline
• TiHKAL

External links

• Tryptamine FAQ
• Tryptamine Hallucinogens and Consciousness
• Lysergic book, describes several tryptamine journeys.
• User-friendly info on Tryptamines, provided by the TRIP! Project, Toronto Canada.
• Tryptamind Psychoactives, reference site on tryptamine and other psychoactives.

Triptans edit
Almotriptan | Eletriptan | Frovatriptan | Naratriptan | Rizatriptan | Sumatriptan | Zolmitriptan

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