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. It is the N-methyl derivative of the psychedelic drug DOB.
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists methyl-DOB's dose as greater than 8mg orally and its duration as "probably rather long". Its onset was about 1.3hours. 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 3mg orally.
At tested doses of 8 to 10mg 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. No clear psychoactive or hallucinogenic effects were described. The drug may also potentiate other psychedelic drugs like even on the next day however, with a "severe response" to a low 5mg dose of psilocybin 24hours later occurring in one instance.
Methyl-DOB shows affinity for the serotonin 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptors (K<sub>i</sub> = 79âÂÂ80nM and 98nM, respectively). Its affinities for serotonin 5-HT<sub>2</sub> receptors were 1.4- to 9.7-fold lower than those of DOB depending on the receptor and radioligand. Methyl-DOB substituted for (R)-DOB in rodent drug discrimination tests, but was approximately 16-fold less potent in comparison.
The chemical synthesis of methyl-DOB has been described.
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.
Methyl-DOB was first described in the scientific literature by Richard Glennon and colleagues by 1987. Subsequently, it was described in greater detail by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.
Methyl-DOB is a controlled substance in Canada under phenethylamine blanket-ban language.