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 kath 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]

Buphedrone

Clinical data
Trade names	Buphedrone
Routes of administration	Vaporization, insufflation, Intravenous injection, intramuscular injection, orally, rectal, buccal
ATC code	none
Legal status
Legal status	DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I
Pharmacokinetic data
Excretion	Urine
Identifiers
IUPAC name 2-(methylamino)-1-phenylbutan-1-one
CAS Number	408332-79-6 Y 166593-10-8 (hydrochloride)
PubChem CID	53249194
ChemSpider	26286946 Y
UNII	VD73947M0O
CompTox Dashboard (EPA)	DTXSID701014170
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(CC)C(=O)c1ccccc1
InChI InChI=1S/C11H15NO/c1-3-10(12-2)11(13)9-7-5-4-6-8-9/h4-8,10,12H,3H2,1-2H3 Y Key:DDPMGIMJSRUULN-UHFFFAOYSA-N Y
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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. The effects of buphedrone have also been compared to methamphetamine, with more euphoria and less physical stimulation. Most commonly reported effects include:

• Elevated mood, euphoria
• Increased alertness
• Dilated pupils (rare)
• Slurred speech (rare)
• Increased heart rate
• Talkativeness
• Increased empathy and sense of communication
• Increased sex drive
• Temporary erectile dysfunction
• Restlessness
• Insomnia
• Increased motivation

Depending on the route of administration, the duration varies from approximately 2.5 (IV) to 6 hours (orally) and may be followed by unpleasant symptoms associated with withdrawal, which may include:

• Dysphoria
• Tiredness
• Sweating
• Loss of concentration

Legal status

As of October 2015, buphedrone is a controlled substance in China.^[3]

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.^[4]

See also

• Pentedrone
• 4-Methylbuphedrone
• 4-Methylpentedrone