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
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See also

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External links



Triptans edit

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

Template:Tryptaminesde:Tryptamin pl:Tryptamina ru:Триптамины

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