Compound: 2,5-Dimethoxy-4-ethylamphetamine
SMILES: O(c1c(cc(OC)c(c1)CC)CC(N)C)C
InChIKey: HXJKWPGVENNMCC-UHFFFAOYSA-N
Synonyms: 2,5-Dimethoxy-4-ethylamphetamine, 22004-32-6, DOET, 4-Ethyl-2,5-dimethoxyamphetamine, 9SK6K682UL, J71.136E, DTXSID00860585, Benzeneethanamine, 4-ethyl-2,5-dimethoxy-alpha-methyl-, Phenethylamine, 4-ethyl-2,5-dimethoxy-alpha-methyl-, RefChem:82893, DTXCID80197306, 1B7JP7F83O, 4-Ethyl-2,5-dimethoxy-alpha-methylphenethylamine hydrochloride, 4-Ethyl-2,5-dimethoxyamphetamine hydrochloride, Benzeneethanamine, 4-ethyl-2,5-dimethoxy-alpha-methyl-, hydrochloride, Phenethylamine, 4-ethyl-2,5-dimethoxy-alpha-methyl-, hydrochloride, 1-(4-ethyl-2,5-dimethoxyphenyl)propan-2-amine, CHEMBL8224, HECATE, 2,5-DIMETHOXY-4-ETHYLAMPHETAMIN, NCGC00247691-01, UNII-9SK6K682UL, DOET,(-), SCHEMBL1740704, BDBM81965, CHEBI:191249, HXJKWPGVENNMCC-UHFFFAOYSA-N, XAA00432, CAS_62066, NSC_62066, PDSP1_000797, PDSP1_001371, PDSP2_000785, PDSP2_001355, DB01467, DB-216732, NS00017969, 2,5-dimethoxy-4-ethylamphetamine (''DOEt''), C22714, 4-Ethyl-2,5-dimethoxy-alpha-methylphenethylamine, L001150, Q947249, 1-(4-Ethyl-2,5-dimethoxyphenyl)-2-propanamine #, PHENETHYLAMINE, 4-ETHYL-2,5-DIMETHOXY-.ALPHA.-METHYL-, (+/-)-1-(2,5-DIMETHOXY-4-ETHYLPHENYL)-2-AMINOPROPANE, (+/-)-4-ETHYL-2,5-DIMETHOXY-.ALPHA.-METHYLPHENETHYLAMINE, BENZENEETHANAMINE, 4-ETHYL-2,5-DIMETHOXY-.ALPHA.-METHYL-
Theoretical properties:
molecular_formula: C13H21NO2
molecular_weight: 223.31 g/mol
exact_mass: 223.157228913 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 5
heavy_atom_count: 16
topological_polar_surface_area: 44.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 2,5-Dimethoxy-4-ethylamphetamine is a member of amphetamines.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: DOET, also known as 4-ethyl-2,5-dimethoxyamphetamine or as Hecate, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The drug is the derivative of DOM in which the methyl group at the 4 position has been replaced with a ethyl group. It is taken orally. DOET has a slow onset of 1 to 3 hours, a delayed peak of 3 to 5 hours, and a dose-dependent and potentially very long duration of 5 to 20 hours.
Effects of DOET at low doses include mild euphoria, enhanced self-awareness, and talkativeness, among others. Mild closed-eye visuals can also occur. At higher doses, DOET produces psychedelic effects including heightened emotions, sensory enhancement, rich closed-eye visuals, and open-eye visuals, among others. Physical effects include pupil dilation, increased heart rate, and increased blood pressure. It acts as a selective agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.
DOET was first discovered by Alexander Shulgin in the 1960s. It was clinically studied at low and sub-hallucinogenic doses for potential use as a pharmaceutical drug acting as a "psychic energizer" by Dow Chemical Company in the 1960s. However, its development was terminated after DOM emerged as a street drug and caused a small public health crisis in San Francisco in 1967. Nonetheless, DOET's effects at low doses were extensively characterized in small clinical trials. The psychedelic effects of DOET at higher doses were subsequently described by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.