Article · Wikipedia archive · Last revised Jun 18, 2026

Meta-DOB

Meta-DOB, also known as 5-bromo-2,4-dimethoxyamphetamine, is a psychoactive drug of the phenethylamine and amphetamine families related to the psychedelic drug DOB. It is a positional isomer of DOB in which the bromine atom at the 4 position and the methoxy group at the 5 position have been interchanged.

Last revised
Jun 18, 2026
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Meta-DOB
Clinical data
Other names5-Bromo-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-bromoamphetamine; 5-Bromo-TMA-2
Routes of
administration		Oral1
Drug classPsychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of action5–6 hours1
Identifiers
  • 1-(5-bromo-2,4-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H16BrNO2
Molar mass274.158 g·mol−1
3D model (JSmol)
  • Brc1cc(c(OC)cc1OC)CC(N)C
  • InChI=1S/C11H16BrNO2/c1-7(13)4-8-5-9(12)11(15-3)6-10(8)14-2/h5-7H,4,13H2,1-3H3 checkY
  • Key:YFSLPSITQIUFQK-UHFFFAOYSA-N checkY
  (verify)

Meta-DOB, also known as 5-bromo-2,4-dimethoxyamphetamine, is a psychoactive drug of the phenethylamine and amphetamine families related to the psychedelic drug DOB.1 It is a positional isomer of DOB in which the bromine atom at the 4 position and the methoxy group at the 5 position have been interchanged.1

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists meta-DOB's dose range as 50 to 100 mg orally and its duration as 5 to 6 hours.1 The effects of meta-DOB have been reported to include MDA-like effects, vague uneasiness, possible threshold psychedelic effects, anxiety, paranoid fantasies, and toxic signs such as flushing, palpitations, and occasional nausea, vomiting, and diarrhea.12 It has been said that any possible psychedelic effects of meta-DOB seem to have been blurred by its more obvious toxic effects.1

The chemical synthesis of meta-DOB has been described.1 A notable analogue of meta-DOB is meta-DOT.1

Meta-DOB was first described in the scientific literature by Silvia Sepúlveda and colleagues by 1972.2 Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.1

See also

See also

References

References

  1. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. Sepúlveda S, Valenzuela R, Cassels BK (April 1972). "Potential psychotomimetics. New bromoalkoxyamphetamines". J Med Chem. 15 (4): 413–415. doi:10.1021/jm00274a022. PMID 5019563.
External links