Tryptamine

Tryptamine
IUPAC name 2-(1H-indol-3-yl)ethanamine
Identifiers
CAS number	61-54-1 Y
PubChem	1150
ChEMBL	CHEMBL6640 N
IUPHAR ligand	125
Jmol-3D images	Image 1
SMILES C1=CC=C2C(=C1)C(=CN2)CCN
Properties
Molecular formula	C10H12N2
Molar mass	160.22 g mol−1
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which it derives its name. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.

The tryptamine chemical structure is the backbone for a group of compounds termed collectively tryptamines. This group includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.

Plants containing tryptamine

Many plants contain small amounts of tryptamine, for example, as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid. Higher concentrations can be found in many Acacia species.

Role in vertebrates

Tryptamine acts as a serotonin releasing agent and a serotonergic activity enhancer. It is metabolised by MAO-A and MAO-B.

Tryptamine derivatives

Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are sometimes 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 common tryptamines.

General structure of substituted tryptamines

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
Tryptamine	Natural	H	H	H	H	H	3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
Bufotenin	Natural	H	H	OH	CH3	CH3	5-hydroxy-N,N-dimethyltryptamine
Nω-methylserotonin (norbufotenin)	Natural	H	H	OH	CH3	H	5-hydroxy-N-methyltryptamine
Serotonin	Natural	H	H	OH	H	H	5-hydroxytryptamine
DMT	Natural	H	H	H	CH3	CH3	N,N-dimethyltryptamine
Melatonin	Natural	H	H	OCH3	O=C-CH3	H	5-methoxy-N-acetyltryptamine
5-Bromo-DMT	Natural	H	H	Br	CH3	CH3	5-bromo-N,N-dimethyltryptamine
5-MeO-DMT	Natural	H	H	OCH3	CH3	CH3	5-methoxy-N,N-dimethyltryptamine
5-MeO-NMT	Natural	H	H	OCH3	CH3	H	5-methoxy-N-methyltryptamine
NMT	Natural	H	H	H	H	CH3	N-methyltryptamine
Norbaeocystin	Natural	H	OPO3H2	H	H	H	4-phosphoryloxy-tryptamine
Baeocystin	Natural	H	OPO3H2	H	CH3	H	4-phosphoryloxy-N-methyl-tryptamine
Psilocybin	Natural	H	PO4	H	CH3	CH3	4-phosphoryloxy-N,N-dimethyltryptamine
Psilocin	Natural	H	OH	H	CH3	CH3	4-hydroxy-N,N-dimethyltryptamine
Tryptophan	Natural	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
O-Acetylpsilocin	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

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

See also

Trace amine beta-Carboline Ergoline

TiHKAL PiHKAL

External links

• Tryptamine FAQ
• Tryptamine Hallucinogens and Consciousness
• Tryptamind Psychoactives, reference site on tryptamine and other psychoactives.
• Tryptamine (T) entry in TiHKAL • info