Tryptamine

Tryptamine
Names


IUPAC name 2-(1H-Indol-3-yl)ethanamine
Identifiers
CAS Number	61-54-1^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL6640^N
ChemSpider	1118^N
ECHA InfoCard	100.000.464
IUPHAR/BPS	125
PubChem	1150
InChI InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2^N Key: APJYDQYYACXCRM-UHFFFAOYSA-N^N InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 Key: APJYDQYYACXCRM-UHFFFAOYAU
SMILES c1ccc2c(c1)c(c[nH]2)CCN
Properties
Chemical formula	C₁₀H₁₂N₂
Molar mass	160.22 g·mol⁻¹
Appearance	white to orange crystalline powder
Melting point	113-116˚C
Boiling point	137˚C (0.15 mmHg)
Solubility in water	negligible solubility in water
Hazards
Flash point	185˚C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

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

Tryptamine is the common functional group in a set of compounds termed collectively substituted tryptamines. This set includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

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

Many plants contain small amounts of tryptamine. It is a feedstock for the metabolic pathways which influence plant growth and microbiome. For example, it is found 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.

Tryptamine acts as a non-selective serotonin receptor agonist and serotonin-norepinephrine-dopamine releasing agent (SNDRA), with a preference for evoking serotonin and dopamine release over norepinephrine release. It is rapidly metabolized by MAO-A and MAO-B, and for this reason, has a very short in vivo half-life.

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Wikipedia