Compound: 2,4-Dimethoxyamphetamine
SMILES: O(c1c(ccc(c1)OC)CC(N)C)C
InChIKey: DQWOZMUBHQPFFF-UHFFFAOYSA-N
Synonyms: 2,4-Dimethoxyamphetamine, 23690-13-3, Benzeneethanamine, 2,4-dimethoxy-alpha-methyl-, GT33R7Q58G, DTXSID90874252, RefChem:1059754, DTXCID901012382, 2,4-DMA, 1-(2,4-dimethoxyphenyl)propan-2-amine, CHEMBL282734, Benzeneethanamine,2,4-dimethoxy-.alpha.-methyl, UNII-GT33R7Q58G, 2,4-dimethoxyamphet-amine, SCHEMBL266899, Benzeneethanamine, 2,4-dimethoxy-alpha-methyl-, (+-)-, SCHEMBL29968339, DQWOZMUBHQPFFF-UHFFFAOYSA-N, BDBM50005264, AKOS000158082, AKOS022196426, 52850-81-4, PD043788, 1-(2,4-Dimethoxyphenyl)-2-propanamine #, NS00018383, 2-(2,4-Dimethoxy-phenyl)-1-methyl-ethylamine, (+/-)2-(2,4-Dimethoxy-phenyl)-1-methyl-ethylamine, 2,4-DIMETHOXY-.ALPHA.-METHYLBENZENEETHANAMINE, PHENETHYLAMINE, 2,4-DIMETHOXY-.ALPHA.-METHYL-, Q27279269, F9994-0711, Benzeneethanamine,2,4-dimethoxy-.alpha.-methyl-(.+/-.)-, Benzeneethanamine, 2,4-dimethoxy-a-methyl-; Phenethylamine, 2,4-dimethoxy-a-methyl- (6CI,8CI); 2,4-Dimethoxy-a-methylbenzeneethanamine; 2,4-Dimethoxyamphetamine; 2,4-DMA
Theoretical properties:
molecular_formula: C11H17NO2
molecular_weight: 195.26 g/mol
exact_mass: 195.125928785 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 14
topological_polar_surface_area: 44.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a psychoactive drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 2,4-DMA's dose as greater than 60 mg orally and its duration as "short". At a dose of 60 mg orally, the effects of 2,4-DMA were reported to include definite threshold effects or even a bit more, a lot of amphetamine-like effects, some euphoria, and a psychedelic-like "diffusion of association". The drug's effects started to wear off after 3 hours. According to Shulgin, 2,4-DMA could be a full stimulant and/or a full psychedelic at sufficiently high doses, but higher doses were not tested.
2,4-DMA has been found to act as a low-potency full agonist of the serotonin 5-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 2,950 nM and an EmaxTooltip half-maximal effective concentration of 117%. It fully substitutes for DOM in rodent drug discrimination tests. The drug is less potent in this regard than 2,4,5-trimethoxyamphetamine (2,4,5-TMA or TMA-2), but is more potent than 3,4,5-trimethoxyamphetamine (3,4,5-TMA or TMA-1). 2,4-DMA fails to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects.
The chemical synthesis of 2,4-DMA has been described.
2,4-DMA was first described in the scientific literature by Alexander Shulgin and colleagues by at least 1967. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.