Methyl-DOB
Pharmaceutical compound
From Wikipedia, the free encyclopedia
Methyl-DOB, or N-methyl-DOB, also known as 4-bromo-2,5-dimethoxy-N-methylamphetamine, MDOB, or M-154, is a psychoactive drug of the phenethylamine, amphetamine, and DOx families.[1] It is the N-methyl derivative of the psychedelic drug DOB.[1]
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| Other names | N-Methyl-DOB; N-Me-DOB; 4-Bromo-2,5-dimethoxy-N-methylamphetamine; MDOB; M-154 |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Psychoactive drug |
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| Onset of action | 1.3 hours[1] |
| Duration of action | "Probably rather long"[1] |
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| Formula | C12H18BrNO2 |
| Molar mass | 288.185 g·mol−1 |
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Use and effects
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists methyl-DOB's dose as greater than 8 mg orally and its duration as "probably rather long".[1] Its onset was about 1.3 hours.[1] Analogously to the case of other N-methylated phenethylamines, the potency of methyl-DOB is dramatically reduced compared to DOB, which has a listed dose of 1 to 3 mg orally.[1]
At tested doses of 8 to 10 mg orally, the effects of methyl-DOB have been reported to include lightheadedness, spaciness, physical effects or body load, tight and rubby teeth, tenseness, exaggerated reflexes, pupil dilation, and next-day hangover.[1] No clear psychoactive or hallucinogenic effects were described.[1] The drug may also potentiate other psychedelic drugs like even on the next day however, with a "severe response" to a low 5 mg dose of psilocybin 24 hours later occurring in one instance.[1]
Interactions
Pharmacology
Pharmacodynamics
Methyl-DOB shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 79–80 nM and 98 nM, respectively).[2][3] Its affinities for serotonin 5-HT2 receptors were 1.4- to 9.7-fold lower than those of DOB depending on the receptor and radioligand.[2][3] Methyl-DOB substituted for (R)-DOB in rodent drug discrimination tests, but was approximately 16-fold less potent in comparison.[3]
Chemistry
Synthesis
The chemical synthesis of methyl-DOB has been described.[1]
Analogues
Analogues of methyl-DOB include N-methyl-DOI, IDNNA (N,N-dimethyl-DOI), N-methyl-2C-B, Beatrice (N-methyl-DOM), N-methyl-DOET, N-methyl-TMA-2, and methyl-TMA (N-methyl-TMA), among others.[1]
History
Methyl-DOB was first described in the scientific literature by Richard Glennon and colleagues by 1987.[3] Subsequently, it was described in greater detail by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1]
Society and culture
Legal status
Methyl-DOB is a controlled substance in Canada under phenethylamine blanket-ban language.[4]