Tryptamine

Tryptamine
Clinical data
Other names	T; TrpA; Triptamine; 3-(2-Aminoethyl)indole; 2-(3-Indolyl)ethylamine; Indolylethylamine; Indolethylamine; PAL-235; PAL235
Routes of; administration	Intravenous injection
Drug class	Serotonin receptor agonist; Trace amine-associated receptor 1 (TAAR1) agonist; Serotonin–norepinephrine–dopamine releasing agent; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Legal status
Legal status	Legal or unregulated;
Pharmacokinetic data
Bioavailability	Oral: Very low
Metabolism	Very rapid (oxidative deamination by MAOTooltip monoamine oxidase)
Metabolites	Indole-3-acetic acid (IAA)
Onset of action	IVTooltip Intravenous injection: Very rapid
Elimination half-life	Very short
Duration of action	IVTooltip Intravenous injection: Very short
Excretion	Urine
Identifiers
	IUPAC name 2-(1H-indol-3-yl)ethan-1-amine;
CAS Number	61-54-1 ;
PubChem CID	1150;
IUPHAR/BPS	125;
DrugBank	DB08653;
ChemSpider	1118 ;
UNII	422ZU9N5TV;
KEGG	C00398;
ChEBI	CHEBI:16765;
ChEMBL	ChEMBL6640 ;
CompTox Dashboard (EPA)	DTXSID2075340 ;
ECHA InfoCard	100.000.464
Chemical and physical data
Formula	C10H12N2
Molar mass	160.220 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	118 °C (244 °F)
Boiling point	137 °C (279 °F) (0.15 mmHg)
Solubility in water	Negligible mg/mL (20 °C)
	SMILES c1ccc2c(c1)c(c[nH]2)CCN;
	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 ;

Tryptamine, also known as 2-(3-indolyl)ethylamine, 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.