Methyl-DOB

Methyl-DOB
Clinical data
Other namesN-Methyl-DOB; N-Me-DOB; 4-Bromo-2,5-dimethoxy-N-methylamphetamine; MDOB; M-154
Routes of
administration		Oral[1]
Drug classSerotonin receptor modulator; Psychoactive drug
ATC code
  • None
Pharmacokinetic data
Onset of action1.3 hours[1]
Duration of action"Probably rather long"[1]
Identifiers
  • 1-(4-bromo-2,5-dimethoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H18BrNO2
Molar mass288.185 g·mol−1
3D model (JSmol)
  • Brc1cc(OC)c(cc1OC)CC(NC)C
  • InChI=1S/C12H18BrNO2/c1-8(14-2)5-9-6-12(16-4)10(13)7-11(9)15-3/h6-8,14H,5H2,1-4H3 Y
  • Key:GURVSGCCXMIFMQ-UHFFFAOYSA-N Y
  (verify)

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]

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

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

Methyl-DOB is a controlled substance in Canada under phenethylamine blanket-ban language.[4]

See also

References

  1. ^ a b c d e f g h i j k l m n Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal127.shtml
  2. ^ a b Glennon RA, Raghupathi R, Bartyzel P, Teitler M, Leonhardt S (February 1992). "Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity". J Med Chem. 35 (4): 734–740. doi:10.1021/jm00082a014. PMID 1542100.
  3. ^ a b c d Glennon RA, Titeler M, Seggel MR, Lyon RA (May 1987). "N-methyl derivatives of the 5-HT2 agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane". J Med Chem. 30 (5): 930–932. doi:10.1021/jm00388a032. PMID 3572981.
  4. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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