Buphedrone, also known as α-methylamino-butyrophenone (MABP), is a

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

and

cathinone Cathinone (; also known as β-ketoamphetamine) is a monoamine alkaloid found in the shrub ''Catha edulis'' (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to t ...

chemical class Chemical classification systems attempt to classify elements or compounds according to certain chemical functional or structural properties. Whereas the structural properties are largely intrinsic, functional properties and the derived classi ...

es that was first synthesized in 1928. It is a synthetic analogue of

, a stimulant naturally occurring in the kath plant. Like many other synthetic cathinones (''e.g.''

mephedrone Mephedrone, also known as , , and , is a synthetic stimulant drug belonging to the amphetamine and cathinone classes. It is commonly referred to by slang names such as drone, , white magic, meow meow, and bubble. Chemically, it is similar to ...

), it is also found in so called "legal highs" (sometimes also called "bath salts"), a class of designer drugs used to bypass legal restrictions.

Chemistry

Buphedrone is a β-ketone and is related to the naturally occurring compounds

and

cathine Cathine, also known as -norpseudoephedrine or as (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine groups which acts as a stimulant. Along with cathinone, it is found naturally in ''Catha edulis'' (khat), and ...

. It is also related to

methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...

, differing by the β-

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

substituent (at the β-carbon) and an

ethyl group In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry The International Union of Pure and Applied ...

replacing the

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

group at the carbon at the α-position relative to the

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

. 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 In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternati ...

being most common.

Effects

Buphedrone increases spontaneous rodent locomotor activity, potentiates the release of

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

from

dopaminergic Dopaminergic means "related to dopamine" (literally, "working on dopamine"), a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain. Dopaminergic pathways, Dopaminergic brain pathways facil ...

nerve A nerve is an enclosed, cable-like bundle of nerve fibers (called axons). Nerves have historically been considered the basic units of the peripheral nervous system. A nerve provides a common pathway for the Electrochemistry, electrochemical nerv ...

terminals in the

brain The brain is an organ (biology), organ that serves as the center of the nervous system in all vertebrate and most invertebrate animals. It consists of nervous tissue and is typically located in the head (cephalization), usually near organs for ...

, and causes

appetite suppression An anorectic is a drug that reduces appetite, resulting in lower food consumption, leading to weight loss. These substances work by affecting the central nervous system or certain neurotransmitters to create a feeling of fullness or reduce the desi ...

. It also causes a possibly dangerous effect of decreasing subjective feeling of thirst. The effects of buphedrone have also been compared to

, with more euphoria and less physical stimulation. Most commonly reported effects include: * Elevated mood,

euphoria Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and da ...

* Increased alertness * Dilated

pupil The pupil is a hole located in the center of the iris of the eye that allows light to strike the retina.Cassin, B. and Solomon, S. (1990) ''Dictionary of Eye Terminology''. Gainesville, Florida: Triad Publishing Company. It appears black becau ...

s (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. Buphedrone is an

Anlage II The following drugs are controlled by the German Narcotic Drugs Act ( or ). Trade and drug possession, possession of these substances without licence or prescription is considered illegal; prescription is illegal for drugs on ''Anlage I'' and II an ...

controlled drug in Germany. In the United States, buphedrone is considered a schedule 1 controlled substance as a positional isomer of

References

{{Phenethylamines Cathinones Designer drugs Norepinephrine-dopamine releasing agents Phenylisobutylamines

Chemistry

Effects

Legal status

See also

References