Compound: ETRYPTAMINE
SMILES: [nH]1c2c(cccc2)c(c1)CC(N)CC
InChIKey: ZXUMUPVQYAFTLF-UHFFFAOYSA-N
Synonyms: ETRYPTAMINE, alpha-Ethyltryptamine, 3-(2-Aminobutyl)indole, 2235-90-7, 3-Indolylbutylamine, Etriptamina, Monase, Ro 3-1932, Etryptaminum, 1H-Indole-3-ethanamine, alpha-ethyl-, alphaET, NSC-88061, DTXSID1046764, GR181O3R32, DTXCID9026764, NSC88061, 2-ethyltryptamine, 3-(2-aminobutylindole), RefChem:139304, 1-(1H-indol-3-yl)butan-2-amine, .alpha.-Ethyltryptamine, Indole, 3-(2-aminobutyl)-, .alpha.et, NSC 88061, 1H-Indole-3-ethanamine, .alpha.-ethyl-, NCGC00168345-01, (+-)-Etryptamine, Etriptamina [DCIT], Etryptamine [INN:BAN], Etryptaminum [INN-Latin], .alpha.-Ethyltryptamine acetate, 1-(1H-Indol-3-ylmethyl)-propylamine, DL-.alpha.-Ethyltryptamine acetate, Indole, 3-(2-aminobutyl)-, acetate, BRN 0146342, INDOLE, 3-(2-AMINOBUTYL)-, MONOACETATE, UNII-GR181O3R32, DEA No. 7249, 1H-Indole-3-ethanamine, .alpha.-ethyl-, monoacetate, a-ethyl tryptamine, alpha-Ethyl-1H-indole-3-ethanamine, 1-(1H-indol-3-ylmethyl)propylamine, alpha-ethyl tryptamine, Alpha-Ethyltryptamine;, AET-, ETRYPTAMINE [MI], ETRYPTAMINE [INN], (.+/-.)-Etryptamine, 1H-Indole-3-ethanamine, alpha-ethyl- (9CI), Etryptamine acetate(USAN), Cambridge id 5119458, TimTec1_002323, A-ETHYLTRYPTAMINE HCL, NCIOpen2_001278, NCIOpen2_002624, Oprea1_329935, Oprea1_455437, 5-22-10-00177 (Beilstein Handbook Reference), (-)-.alpha.-Ethyltryptamine, SCHEMBL606067, CHEMBL1619758, SCHEMBL29395670, WLN: T56 BMJ D1YZ2, CHEBI:134838, HMS1540J13, Tox21_112618, BDBM50025198, STK236313, ETRYPTAMINE [INCB GREEN LIST], AKOS000623809, AKOS022066248, 1-(1H-Indol-3-yl)-2-butanamine #, DB01546, NCGC00168345-02, NCGC00168345-03, 1-(1H-Indol-3-yl)-2-butanamine acetate, CAS-2235-90-7, NS00005549, AB00690746-07, Indole-3-ethylamine, .alpha.-ethyl-, monoacetate, Q2394183
Theoretical properties:
molecular_formula: C12H16N2
molecular_weight: 188.27 g/mol
exact_mass: 188.131348519 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 3
heavy_atom_count: 14
topological_polar_surface_area: 41.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Etryptamine is a member of indoles.
chembl: ETRYPTAMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.
Side effects of αET include facial flushing, headache, gastrointestinal distress, insomnia, irritability, appetite loss, and sedation, among others. A rare side effect of αET is agranulocytosis. αET acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a weak serotonin receptor agonist, and as a weak monoamine oxidase inhibitor. It may also produce serotonergic neurotoxicity. αET is a substituted tryptamine and is closely related to α-methyltryptamine (αMT) and other α-alkylated tryptamines.
αET was first described in 1947. It was used as an antidepressant for about a year around 1961. The drug started being used recreationally in the 1980s and several deaths have been reported. αET is a controlled substance in various countries, including the United States and United Kingdom. There has been renewed interest in αET, for instance as an alternative to MDMA, with the development of psychedelics and entactogens as medicines in the 2020s.