Compound: alpha-Methyltryptamine
SMILES: [nH]1c2c(cccc2)c(c1)CC(N)C
InChIKey: QSQQQURBVYWZKJ-UHFFFAOYSA-N
Synonyms: alpha-Methyltryptamine, Indopan, 299-26-3, alpha-Methyl-beta-indoleethylamine, 1-(1H-Indol-3-yl)-2-propanamine, alpha-Methyl-1H-indole-3-ethanamine, alpha-Methyl-3-indoleethanamine, INDOLE, 3-(2-AMINOPROPYL)-, Ro 3-0926, (+-)-alpha-Methyltryptamine, alphaMT, BIK35ACJ0Q, 1H-Indole-3-ethanamine, alpha-methyl-, 164 E, NSC-97069, CHEBI:59020, RefChem:790997, 206-073-7, 3-(2-Aminopropyl)indole, 1-(1H-indol-3-yl)propan-2-amine, DL-3-(2-Aminopropyl)indole, IT-403(D), .alpha.-Methyltryptamine, U 14164 E, NSC 97069, 164E, U 14, 1H-Indole-3-ethanamine, .alpha.-methyl-, .alpha.-Methyl-.beta.-indoleethylamine, It-290(dl), u-14164e(dl), CHEMBL30713, .alpha.-Methyl-3-indoleethanamine, MFCD00005654, DL-alfa-methyltryptamine, 1-indol-3-ylprop-2-ylamine, 304-54-1, DL-alpha-Methyltryptamine, alpha-Methyl-beta-indolaethylamine, Spirals [Street Name], U 14 (VAN), IT-290(D,L), EINECS 206-073-7, UNII-BIK35ACJ0Q, U-14164E(D,L), BRN 0140457, alpha-Methyl-beta-indolaethylamine [German], (+-)-alpha-Methyl-1H-indole-3-ethanamine, DTXSID00861850, INDOLE, 3-(2-AMINOPROPYL)-, (+-)-, a-methyl tryptamine, SPIRALS, alpha-Methyl tryptamine, 2-(1H-indol-3-yl)-1-methylethylamine, .ALPHA.MT, AMT-, 1H-Indole-3-ethanamine, alpha-methyl- (9CI), Tryptamine, .alpha.-methyl, 1H-Indole-3-ethanamine, alpha-methyl-, (+-)-, Oprea1_004262, alpha-Methyltryptamine, 99%, 5-22-10-00144 (Beilstein Handbook Reference), SCHEMBL274268, (+/-)-alpha-methyltryptamine, SCHEMBL4657384, SCHEMBL7873795, DEA No. 7432, WLN: T56 BMJ D1YZ1, .ALPHA.-METHYLTRYPTAMINE-, DL-.ALPHA.-METHYLTRYPTAMINE, NSC97069, BDBM50014210, DL-alpha-Methyltryptamine, free base, PDSP1_000039, PDSP1_000947, PDSP2_000039, PDSP2_000933, SBB003798, STK926814, .ALPHA.-METHYLTRYPTAMINE [MI], AKOS000276077, AKOS016041665, .alpha.-methyl-.beta.-indolaethylamine, 3-(2-AMINOPROPYL)-1H-INDOLE, DB01446, 1-(1H-Indol-3-yl)-2-propanamine #, (+/-)-.ALPHA.-METHYLTRYPTAMINE, 1H-Indole-3-ethanamine, .alpha.-methyl, NCGC00332100-01, NCGC00332100-02, 2-(1H-Indol-3-yl)-1-methyl-ethylamine, AC-28321, [2-(1H-indol-3-yl)-1-methylethyl]amine, DB-006231, NS00017916, ST50307961, rac. 2-(1H-indol-3-yl)-1-methylethylamine, C20127, M-4620, AB01325935-02, Q421163
Theoretical properties:
molecular_formula: C11H14N2
molecular_weight: 174.24 g/mol
exact_mass: 174.115698455 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 2
heavy_atom_count: 13
topological_polar_surface_area: 41.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 98-100 °C
Descriptions:
pubchem: Alpha-methyltryptamine is a tryptamine derivative having a methyl substituent at the alpha-position.
chebi: A tryptamine derivative having a methyl substituent at the α-position.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and α-alkyltryptamine families. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.
Side effects of αMT include agitation, restlessness, confusion, lethargy, pupil dilation, jaw clenching, and rapid heart rate, among others. αMT acts as a releasing agent of serotonin, norepinephrine, and dopamine, as a serotonin receptor agonist, and as a weak monoamine oxidase inhibitor. αMT is a substituted tryptamine and is closely related to α-ethyltryptamine (αET) and other α-alkylated tryptamines.
αMT appears to have first been described by at least 1929. It started being more studied in the late 1950s and was briefly used as an antidepressant in the Soviet Union in the 1960s. The drug started being used recreationally in the 1960s, with use increasing in the 1990s, and cases of death have been reported. αMT is a controlled substance in various countries, including the United States.