Chemistry:Buphedrone
Buphedrone, also known as α-methylamino-butyrophenone (MABP), 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). It mediates this action by reversing the VMAT2, causing an efflux of the monoamines; dopamine, norepinephrine, and, to a lesser extent, serotonin.
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]
Legal status
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
- ↑ "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society 50 (8): 2287–2292. August 1928. doi:10.1021/ja01395a032. Bibcode: 1928JAChS..50.2287H.
- ↑ "The new designer drug buphedrone produces rewarding properties via dopamine D1 receptor activation". Addiction Biology 23 (1): 69–79. January 2018. doi:10.1111/adb.12472. PMID 27790823.
- ↑ "Designer Cathinones N-Ethylhexedrone and Buphedrone Show Different In Vitro Neurotoxicity and Mice Behaviour Impairment" (in en). Neurotoxicity Research 39 (2): 392–412. 2021. doi:10.1007/s12640-020-00229-6. ISSN 1029-8428. https://link.springer.com/10.1007/s12640-020-00229-6.
- ↑ "The new designer drug buphedrone produces rewarding properties via dopamine D1 receptor activation" (in en). Addiction Biology 23 (1): 69–79. 2016. doi:10.1111/adb.12472. ISSN 1355-6215. https://onlinelibrary.wiley.com/doi/10.1111/adb.12472.
- ↑ "GHB and synthetic cathinones: clinical effects and potential consequences" (in en). Drug Testing and Analysis 3 (9): 552–559. 2010. doi:10.1002/dta.210. ISSN 1942-7603. https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/dta.210.
- ↑ "Synthetic cathinones - Alcohol and Drug Foundation" (in en). https://adf.org.au/drug-facts/synthetic-cathinones/.
- ↑ "Error: no
|title=specified when using {{Cite web}}" (in zh). China Food and Drug Administration. 27 September 2015. http://www.sfda.gov.cn/WS01/CL0056/130753.html. - ↑ "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". U.S. Department of Justice. February 2023. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf.
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