Beatrice (drug)
Psychoactive drug
From Wikipedia, the free encyclopedia
Beatrice, also known as 4-methyl-2,5-dimethoxy-N-methylamphetamine or as N-methyl-DOM, MDOM, or MDO-D, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families.[1][2] It is a substituted methamphetamine and a homologue of 2,5-dimethoxy-4-methylamphetamine (DOM).[1][2]
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| Other names | BEATRICE; Béa; 4-Methyl-2,5-dimethoxy-N-methylamphetamine; 2,5-Dimethoxy-4-methyl-N-methylamphetamine; 2,5-Dimethoxy-4,N-dimethylamphetamine; N-Methyl-DOM; MDO-D; MDOM |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Psychoactive drug; Stimulant |
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| Duration of action | 6–10 hours[1] |
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| Formula | C13H21NO2 |
| Molar mass | 223.316 g·mol−1 |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists Beatrice's dose as above 30 mg orally and its duration as 6 to 10 hours.[1][2] At tested doses of 20 to 30 mg orally, the effects of Beatrice have been reported to include openness, eroticism, responsivity, stimulant-like effects, physical effects, muscle tremors, restlessness, sleeping difficulties, diarrhea, and no appetite loss.[1] No clear hallucinogenic effects were described.[1] It is on the order of 10-fold less potent as a psychoactive drug than DOM and is further less potent in terms of hallucinogenic effects.[1] Shulgin hypothesized that Beatrice might produce psychedelic effects at a dose of 75 mg orally, but did not feel comfortable exploring this level.[1] The drug is one of Shulgin's "ten classic ladies", a series of methylated DOM derivatives.[1][3]
Interactions
Pharmacology
Pharmacodynamics
Beatrice shows affinity for serotonin receptors.[4][5] Its affinities (Ki) were 415 nM for the 5-HT2 receptor and 3,870 nM for the 5-HT1 receptor.[4][5] The affinity of Beatrice for the serotonin 5-HT2 receptor was about 4-fold lower than that of DOM.[4][5] Functional activities were not reported.[4][5]
Beatrice fully substituted for DOM in rodent drug discrimination tests, albeit with approximately 9-fold lower potency in comparison.[6][7][8]
Chemistry
Synthesis
The chemical synthesis of Beatrice has been described.[1]
Analogues
Analogues of Beatrice include N-methyl-DOET, N-methyl-DOI, N-methyl-DOB, IDNNA (N,N-dimethyl-DOI), N-methyl-TMA-2, and methyl-TMA (N-methyl-TMA), among others.[1][2][9][10] N-Methyl-DOI is a potent agonist of the serotonin 5-HT2A receptor similarly to DOI, but with several-fold reduced potency and slightly reduced efficacy.[10]
History
Beatrice was first described in the scientific literature by Beng T. Ho and colleagues in 1970.[11] Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
Legal status
Canada
Beatrice is a controlled substance in Canada under phenethylamine blanket-ban language.[12]
United States
In the United States, Beatrice is a Schedule I isomer of DOET.[13][14]