Tryptamine

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From Wikipedia, the free encyclopedia
This article is about the specific substance. For the class of substances,
see substituted tryptamine.

Tryptamine

Names

Preferred IUPAC name

2-(1H-Indol-3-yl)ethan-1-amine

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  DTXSID2075340
Dashboard (EPA)

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InChI

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SMILES

Properties

Chemical formula C10H12N2

Molar mass 160.220 g·mol−1

Appearance white to orange crystalline powder[1]

Melting point 113-116˚C[1]

Boiling point 137 °C (279 °F; 410 K) (0.15 mmHg)[1]

Solubility in water negligible solubility in water[1]

Hazards

Flash point 185˚C[1]

Except where otherwise noted, data are given for materials in

their standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

Tryptamine is an indolamine metabolite of the essential amino

acid, tryptophan.[2][3] 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).[2] 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.[2][4][5][6] Tryptamine
has been shown to activate trace amine-associated receptors expressed in the
mammalian brain, and regulates the activity
of dopaminergic, serotonergic and glutamatergic systems.[7] [8] In the human gut,
symbiotic bacteria convert dietary tryptophan to tryptamine, which activates 5-
HT4 receptors and regulates gastrointestinal motility.[3][9][10] 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.[11][12][13]