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Buphedrone

Stimulant drug and research chemical

Field	Value
verifiedrevid	462768752
IUPAC_name	2-(methylamino)-1-phenylbutan-1-one
image	Buphedrone.svg
image_class	skin-invert-image
width	200
image2	Buphedrone.png
image_class2	bg-transparent
width2	200
<!--Clinical data-->	tradename	Buphedrone
routes_of_administration	Vaporization, insufflation, Intravenous injection, intramuscular injection, orally, rectal, buccal
legal_DE	Anlage II
legal_UK	Class B
<!--Pharmacokinetic data-->	legal_US	Schedule I
excretion	Urine
<!--Identifiers-->	CAS_number_Ref
CAS_number	408332-79-6
CAS_supplemental
(hydrochloride)
ATC_prefix	none
ChemSpiderID_Ref
ChemSpiderID	26286946
PubChem	53249194
UNII_Ref
UNII	VD73947M0O
<!--Chemical data-->	C	11
H	15
N	1
O	1
smiles	CNC(CC)C(=O)c1ccccc1
StdInChI_Ref
StdInChI	1S/C11H15NO/c1-3-10(12-2)11(13)9-7-5-4-6-8-9/h4-8,10,12H,3H2,1-2H3
StdInChIKey_Ref
StdInChIKey	DDPMGIMJSRUULN-UHFFFAOYSA-N

(hydrochloride)

Buphedrone, also known as α-methylamino-butyrophenone (MABP), is a stimulant of the phenethylamine and cathinone chemical classes that was first synthesized in 1928. 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.

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, potentiates the release of dopamine from dopaminergic nerve terminals in the brain, 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, in general it is expected to have overlapping effects with other synthetic cathinones.

Legal status

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

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.

References

(August 1928). "Synthetic Homologs of d,l-Ephedrine". Journal of the American Chemical Society.
(January 2018). "The new designer drug buphedrone produces rewarding properties via dopamine D1 receptor activation". Addiction Biology.
(2021). "Designer Cathinones N-Ethylhexedrone and Buphedrone Show Different In Vitro Neurotoxicity and Mice Behaviour Impairment". Neurotoxicity Research.
(2016). "The new designer drug buphedrone produces rewarding properties via dopamine D1 receptor activation". Addiction Biology.
(2010). "GHB and synthetic cathinones: clinical effects and potential consequences". Drug Testing and Analysis.
"Synthetic cathinones - Alcohol and Drug Foundation".
(27 September 2015). link. China Food and Drug Administration
(February 2023). "Lists of: Scheduling Actions Controlled Substances Regulated Chemicals". U.S. Department of Justice.

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

cathinones designer-drugs norepinephrine-dopamine-releasing-agents phenylisobutylamines

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