Tryptamine

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Tryptamine
Image:Tryptamine.png
Image:Tryptamine-3d-sticks.png
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 1 Plants containing tryptamine 2 Tryptamine derivatives 3 References 4 See also 5 External links

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

See also

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

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.

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

Template:Triptans

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

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