β-Methyl-DOM, or β-Me-DOM, also known as 4-methyl-2,5-dimethoxy-β-methylamphetamine, is a chemical compound of the phenethylamine, amphetamine, and DOx families related to DOM. "The two beta-hydrogen atoms of DOM are distinct in that, upon being replaced with methyl groups, one would produce a threo-isomer, and the other an erythro-isomer. I have named them DAPHNE (who escaped from Apollo by becoming a laurel tree which was, incidentally, named for her) and ELVIRA (who might not be too well known classically, but whose name has been attached to Mozart’s 21st piano concerto as its slow movement was used as theme music for the movie Elvira Madigan). I don’t know if either of this pair has been made—I started and got as far as the cis-trans mixture of adducts between nitroethane and 2,5-dimethoxy-4-methylacetophenone. Whoever finally makes them gets to assign the names. I had made and tested the corresponding homologues of DMMDA that correspond to these two ladies." [...] "The similar analogues for DOM are the two Classic Ladies, DAPHNE and ELVIRA, and they, too, are for some time in the future." It has two notable enantiomers, Daphne (threo-β-Me-DOM) and Elvira (erythro-β-Me-DOM). These compounds are two of Alexander Shulgin's "ten classic ladies", a series of methylated DOM derivatives that Shulgin explored as part of DOM structure–activity relationship research.
Shulgin partially completed the syntheses of Daphne and Elvira, but did not fully synthesize nor test them and their properties and effects are unknown. β-Methyl-DOM has been reported to have virtually no hallucinogen-like activity in animals, but did produce hyperthermia at high doses.
The compound was first described in the scientific literature by F. Aldous and colleagues in 1974 and was further described by Shulgin, as the enantiomers Daphne and Elvira, in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991. It is a controlled substance in Canada under phenethylamine blanket-ban language. The drug is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of DOET.
See also DOx (psychedelics) β-Methyl-2C-B (BMB) DMCPA, 2CB-Ind, and TCB-2 ZC-B, 2C-B-PYR, and LPH-5
References
External links β-Me-DOM - Isomer Design DAPHNE (threo-β-Me-DOM) - Isomer Design ELVIRA (erythro-β-Me-DOM) - Isomer Design ARIADNE (discusses Daphne and Elvira) - PiHKAL - Erowid ARIADNE (discusses Daphne and Elvira) - PiHKAL - Isomer Design