Meta-DOB

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Meta-DOB
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Clinical data
Other names5-Bromo-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-bromoamphetamine; 5-Bromo-TMA-2
Routes of
administration		Oral[1]
Drug classPsychoactive drug
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  • None
Pharmacokinetic data
Duration of action5–6 hours[1]
Identifiers
  • 1-(5-bromo-2,4-dimethoxyphenyl)propan-2-amine
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Chemical and physical data
FormulaC11H16BrNO2
Molar mass274.158 g·mol−1
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  • 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
Data page
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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.[1][2] 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

References

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  1. ^ a b c d e f g h i j Page Module:Citation/CS1/styles.css has no content.Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ a b Page Module:Citation/CS1/styles.css has no content.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.

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