Tryptamine

Tryptamine
Names
	Preferred IUPAC name 2-(1H-Indol-3-yl)ethan-1-amine
	Other names T; Triptamine; β-(3-Indolyl)ethylamine; Indolylethylamine; Indolethylamine; PAL-235; PAL235
Identifiers
CAS Number	61-54-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	125513
ChEBI	CHEBI:16765;
ChEMBL	ChEMBL6640 ;
ChemSpider	1118 ;
DrugBank	DB08653;
ECHA InfoCard	100.000.464
IUPHAR/BPS	125;
KEGG	C00398;
PubChem CID	1150;
UNII	422ZU9N5TV ;
CompTox Dashboard (EPA)	DTXSID2075340 ;
	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 Key: APJYDQYYACXCRM-UHFFFAOYSA-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	160.220 g·mol−1
Appearance	white to orange needles
Melting point	118˚C
Boiling point	137 °C (279 °F; 410 K) (0.15 mmHg)
Solubility in water	negligible solubility in water
Pharmacology
Drug class	Serotonin receptor agonist; Trace amine-associated receptor 1 (TAAR1) agonist; Serotonin–norepinephrine–dopamine releasing agent; Serotonergic psychedelic; Hallucinogen
Routes of; administration	Intravenous
	Pharmacokinetics:
Bioavailability	Very low
Metabolism	Very rapid (oxidative deamination by MAOTooltip monoamine oxidase)
Metabolites	Indole-3-acetic acid (IAA)
Onset of action	Very rapid
Biological half-life	Very short
Duration of action	Very short
Excretion	Urine
Legal status	Legal or unregulated;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.

Tryptamine has been shown to activate serotonin receptors and trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems. In the human gut, bacteria convert dietary tryptophan to tryptamine, which activates 5-HT₄ receptors and regulates gastrointestinal motility.

Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.