Buphedrone

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Buphedrone
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Clinical data
Trade namesBuphedrone
Other names2-(Methylamino)butanophenone; α-Methylaminobutyrophenone; MABP; NM-BP; PAL-429; PAL429; β-Keto-N-methylphenylisobutylamine; α-Ethyl-β-keto-N-methylphenethylamine; β-Keto-N-methyl-α-ethylphenethylamine; β-Keto-α-ethyl-N-methylphenethylamine
Routes of
administration		Vaporization, insufflation, Intravenous injection, intramuscular injection, orally, rectal, buccal
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  • none
Legal status
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Pharmacokinetic data
ExcretionUrine
Identifiers
  • 2-(methylamino)-1-phenylbutan-1-one
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Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
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  • CNC(CC)C(=O)c1ccccc1
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Buphedrone, also known as β-keto-N-methylphenylisobutylamine, is a stimulant of the phenethylamine and cathinone chemical classes that was first synthesized in 1928.[1] It is a synthetic analogue of cathinone, a stimulant naturally occurring in the khat plant. Like many other synthetic cathinones (e.g. mephedrone), it is also found in so called "legal highs" (sometimes also called "bath salts"), a class of designer drugs used to bypass legal restrictions.[2]

Pharmacology

Buphedrone is a substituted cathinone, and more broadly related, a substituted amphetamine and substituted phenethylamine and, as such, operates as a norepinephrine-dopamine releasing agent, similar to many of the drugs in its chemical class(es).

Chemistry

Buphedrone is a β-ketone and is related to the naturally occurring compounds cathinone and cathine. It is also related to methamphetamine, differing by the β-ketone substituent (at the β-carbon) and an ethyl group replacing the methyl group at the carbon at the α-position relative to the amine. Another name for buphedrone is phenylacetoethyl-methylamine.

Buphedrone as free base is very unstable; it is prone to dimerization like other α-amino ketones. Because of this, it is sold as various salts, with a hydrochloride being most common.

Effects

Buphedrone increases spontaneous rodent locomotor activity,[3] potentiates the release of dopamine from dopaminergic nerve terminals in the brain,[4] and causes appetite suppression. It also causes a possibly dangerous effect of decreasing subjective feeling of thirst. Though the specific effects and toxicity of buphedrone are not well studied,[5] in general it is expected to have overlapping effects with other synthetic cathinones.[6]

As of October 2015, buphedrone is a controlled substance in China.[7]

Buphedrone is an Anlage II controlled drug in Germany.

In the United States, buphedrone is considered a schedule 1 controlled substance as a positional isomer of mephedrone.[8]

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Hyde JF, Browning E, Adams R (August 1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society. 50 (8): 2287–2292. Bibcode:1928JAChS..50.2287H. doi:10.1021/ja01395a032.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Oh JH, Hwang JY, Hong SI, Ma SX, Seo JY, Lee SY, et al. (January 2018). "The new designer drug buphedrone produces rewarding properties via dopamine D1 receptor activation". Addiction Biology. 23 (1): 69–79. doi:10.1111/adb.12472. PMID 27790823.
  3. ^ Page Module:Citation/CS1/styles.css has no content.de Mello-Sampayo C, Vaz AR, Henriques SC, Fernandes A, Paradinha F, Florindo P, et al. (2021). "Designer Cathinones N-Ethylhexedrone and Buphedrone Show Different In Vitro Neurotoxicity and Mice Behaviour Impairment". Neurotoxicity Research. 39 (2): 392–412. doi:10.1007/s12640-020-00229-6. ISSN 1029-8428.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Oh JH, Hwang JY, Hong SI, Ma SX, Seo JY, Lee SY, et al. (2016). "The new designer drug buphedrone produces rewarding properties via dopamine D1 receptor activation". Addiction Biology. 23 (1): 69–79. doi:10.1111/adb.12472. ISSN 1355-6215.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Karila L, Reynaud M (2010). "GHB and synthetic cathinones: clinical effects and potential consequences". Drug Testing and Analysis. 3 (9): 552–559. doi:10.1002/dta.210. ISSN 1942-7603.
  6. ^ Page Module:Citation/CS1/styles.css has no content."Synthetic cathinones - Alcohol and Drug Foundation". adf.org.au. Retrieved 2025-09-22.
  7. ^ Page Module:Citation/CS1/styles.css has no content.关于印发《非药用类麻醉药品和精神药品列管办法》的通知 (in 中文). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Lists of: Scheduling Actions Controlled Substances Regulated Chemicals" (PDF). U.S. Department of Justice. February 2023. Retrieved 7 March 2023.

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