Compound: tryptamine
SMILES: [nH]1c2c(cccc2)c(c1)CCN
InChIKey: APJYDQYYACXCRM-UHFFFAOYSA-N
Synonyms: tryptamine, 61-54-1, 2-(1H-Indol-3-yl)ethanamine, 3-(2-aminoethyl)indole, 1H-Indole-3-ethanamine, 2-(3-Indolyl)ethylamine, 2-(1H-Indol-3-Yl)Ethan-1-Amine, Indole, 3-(2-aminoethyl)-, beta-(3-Indolyl)ethylamine, 422ZU9N5TV, CHEBI:16765, DTXSID2075340, NSC-165212, 3-[2-Aminoethyl]indole, RefChem:900684, DTXCID3042922, 200-510-5, Indol-3-ethylamine, Tryptamin, 2-(Indol-3-yl)ethylamine, MFCD00005661, 2-(1H-indol-3-yl)ethylamine, 3-Indoleethylamine, 3-(2-Aminoethyl)-1H-indole, 2-Indol-3-ylethylamine, 3-Indoleethanamine, (Amino-2 ethyl)-3 indole, (Amino-2 ethyl)-3 indole [French], BRN 0125513, 2-(1H-INDOL-3-YL)-ETHYLAMINE, CHEMBL6640, .beta.-(3-Indolyl)ethylamine, Tryptamine, free base, EINECS 200-510-5, triptamine, UNII-422ZU9N5TV, CCRIS 8959, SR-01000075589, 3-indolylethylamine, TSH, Tryptamine, 98%, (3-Indolyl)ethylamine, Spectrum_000033, TRYPTAMINE [MI], Spectrum2_000873, Spectrum3_001890, Spectrum4_000850, Spectrum5_001296, 2-indol-3-yl-ethylamine, 2-Indol-3-yl-aethylamin, 3-(2-amino)ethyl indole, bmse000207, EC 200-510-5, Lopac-246557, 3-(beta-aminoethyl)-indole, Epitope ID:2279310, Lopac0_000061, Oprea1_870097, SCHEMBL26725, BSPBio_003400, GTPL125, KBioGR_001459, KBioSS_000393, 5-22-10-00045 (Beilstein Handbook Reference), MLS000515794, DivK1c_000862, SPECTRUM1503922, SPBio_000945, Tryptamine, analytical standard, orb1310418, orb3140229, SCHEMBL3266296, SCHEMBL4656420, SCHEMBL16432092, SCHEMBL20970974, SCHEMBL27851522, SCHEMBL29373222, 2-(1h-indol-3-yl) ethylamine, HMS502L04, KBio1_000862, KBio2_000393, KBio2_002961, KBio2_005529, KBio3_002903, NINDS_000862, 2-(1H-indol-3-yl)-ethyl-amine, HMS1922K18, HMS2267B18, HMS3885E17, HMS5081D12, 2-(1H-Indol-3-yl)ethanamine #, ALBB-017957, CS-D1750, HY-B2132, BBL015353, BDBM50024210, CCG-40088, EBC-01032, s3627, SBB003963, STK262895, AKOS000119468, DB08653, FS-3317, MSK001616-100W, SDCCGMLS-0066798.P001, SDCCGSBI-0050049.P003, IDI1_000862, MSK001616-1000W, NCGC00014994-01, NCGC00014994-02, NCGC00014994-03, NCGC00014994-04, NCGC00014994-05, NCGC00014994-06, NCGC00014994-07, NCGC00014994-10, NCGC00014994-11, NCGC00095081-01, NCGC00095081-02, NCGC00095081-03, NCGC00095081-04, NCGC00095081-05, Tryptamine Solution in Water, 100ug/mL, BP-12561, SMR000112268, SY001383, Tryptamine Solution in Water, 1000ug/mL, DB-005731, Tryptamine, Vetec(TM) reagent grade, 98%, NS00006933, ST50308344, T0647, EN300-20412, C00398, T-8095, T-8100, AE-848/30735051, F091543, L000946, Q409439, SR-01000075589-5, BRD-K44218819-001-05-1, F2169-0960, Z104478080, 5E7B376B-5933-446C-9D88-661B5F480122, InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H
Theoretical properties:
molecular_formula: C10H12N2
molecular_weight: 160.22 g/mol
exact_mass: 160.100048391 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 12
topological_polar_surface_area: 41.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 114 - 119 °C
Descriptions:
pubchem: Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is a member of tryptamines, an aminoalkylindole, an indole alkaloid and an aralkylamino compound. It is a conjugate base of a tryptaminium.
chebi: An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position.
chembl: TRYPTAMINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.