Compound: 1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine
SMILES: O(c1c(cc(OC)c(c1)C)CC(N)CC)C
InChIKey: MLYCFWZIAJAIGW-UHFFFAOYSA-N
Synonyms: 1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine, BL3912 free base, Ariadne, BL-3912 free base, Dimoxamine, (+/-)-, alpha-EH Dom, alpha-Ethyl 2c-d, 8AE293HY9Y, UNII-8AE293HY9Y, 52842-58-7, 4-Methyl-2,5-dimethoxy-alpha-ethylphenethylamine, alpha-Ethyl-2,5-dimethoxy-4-methylbenzeneethanamine, Benzeneethanamine, alpha-ethyl-2,5-dimethoxy-4-methyl-, Benzeneethanamine, alpha-ethyl-2,5-dimethoxy-4-methyl-, (+/-)-, Ariadne (psychedelic), .ALPHA.-EH DOM, 4C-DOM, .ALPHA.-ET-2C-D, Oprea1_785590, SCHEMBL43489, CBDivE_007620, .ALPHA.-ETHYL 2C-D, SCHEMBL29543489, BDBM674375, DTXSID501343240, US20240166618, Compound 25, 2,5-dimethoxy-4-methyl-alpha-ethyl-phenethylamine, Q4790178, .ALPHA.-ETHYL-2,5-DIMETHOXY-4-METHYLBENZENEETHANAMINE, BENZENEETHANAMINE, .ALPHA.-ETHYL-2,5-DIMETHOXY-4-METHYL-, BENZENEETHANAMINE, .ALPHA.-ETHYL-2,5-DIMETHOXY-4-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": null, "chebi": null, "chembl": null, "wikipedia": "Ariadne, also known chemically as 4C-D or 4C-DOM, by its developmental code name BL-3912, and by its former tentative brand name Dimoxamine, is a non-hallucinogenic psychoactive drug of the phenethylamine, phenylisobutylamine (\u03b1-ethylphenethylamine), and 4C families. It is a close analogue of the psychedelic drugs 2C-D and DOM, with 2C-D having no substitution at the \u03b1 carbon, DOM having an \u03b1-methyl group, and Ariadne having an \u03b1-ethyl group. Ariadne is taken orally.\nThe drug is a serotonin 5-HT2 receptor partial agonist, including of the serotonin 5-HT2A receptor, similarly to psychedelics. However, Ariadne is not hallucinogenic in humans, but is still psychoactive, producing antidepressant and mild stimulant effects such as feelings of well-being and mental alertness. The drug shows dopaminergic actions in animals, such as increased motivation and reversal of parkinsonism, which may be mediated by serotonin 5-HT2A receptor activation-induced dopamine release in the brain. It is thought that the non-psychedelic nature of Ariadne with retained psychoactive effects is due to reduced but still high efficacy at the serotonin 5-HT2A receptor relative to psychedelics.\nAriadne was first synthesized by Alexander Shulgin in 1968 and its psychoactive effects were discovered by Shulgin in 1969. It was developed as a potential pharmaceutical drug at Bristol Laboratories, for instance as an antidepressant and for various other uses, and entered clinical trials around 1974. The drug reached phase 3 trials prior to its development being shelved. The development of Ariadne is said to have been discontinued for strategic economic reasons rather than due to issues with effectiveness or safety. There has been renewed interest in Ariadne and similar drugs in the 2020s owing to increased interest in psychedelics for treatment of psychiatric disorders. Ariadne is not an explicitly controlled substance in the United States, but may be considered Schedule I as an isomer of DOET."}