Structure via PubChem · Public domain (PubChem)
Meta-DOB
Sign in to saveMeta-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.
Chemical data
- Formula
- C11H16BrNO2
- Molecular weight
- 274.15 g/mol
- IUPAC name
- 1-(5-bromo-2,4-dimethoxyphenyl)propan-2-amine
- SMILES
- CC(CC1=CC(=C(C=C1OC)OC)Br)N
- InChIKey
- YFSLPSITQIUFQK-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 44.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 273.036441
Show 2 more facts
- chemical formula
- C₁₁H₁₆BrNO₂
- canonical SMILES
- CC(CC1=CC(=C(C=C1OC)OC)Br)N
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
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.
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists meta-DOB's dose range as 50 to 100mg orally and its duration as 5 to 6hours. 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. It has been said that any possible psychedelic effects of meta-DOB seem to have been blurred by its more obvious toxic effects.
Excerpted from Wikipedia’s “Meta-DOB” article, available under the CC BY-SA 4.0 licence.