Dextroamphetamine is the dextrorotary, or "right-handed", stereoisomer of the amphetamine molecule. The amphetamine molecule has two stereoisomers; levoamphetamine and dextroamphetamine. Names for dextroamphetamine include d-amphetamine, dexamphetamine, dexamfetamine, and (S)-(+)-amphetamine, with brand names to include Dexedrine and Dextrostat. It is the active metabolite of the prodrug, lisdexamfetamine, known by its brand name VyvanseShire). (marketed by
The dextroamphetamine salts constitute 50% of the ADHD drug Adderall,[1] which consists of racemic d,l-amphetamine. In addition, dextroamphetamine is an active metabolite of several older N-substituted amphetamine prodrugs used as anorectics, such as clobenzorex (Asenlix), benzphetamine (Didrex), and amphetaminil (Aponeuron).
amphetamine was first synthesized under the chemical name "phenylisopropylamine" in Berlin, 1887 by the Romanian chemist Lazar Edeleanu.[2] It was not widely marketed until 1932, when the pharmaceutical company Smith, Kline & French (now known as GlaxoSmithKline) introduced it in the form of the Benzedrine inhaler for use as a bronchodilator. Notably, the amphetamine contained in the Benzedrine inhaler was the liquid free-base,[n 1] not a chloride or sulfate salt.
Three years later, in 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced tablets under the tradename Dexedrine.[3] In the United States, Dexedrine was approved to treat narcolepsy, attention disorders, depression, and obesity. Dextroamphetamine was marketed in various other forms in the following decades, primarily by Smith, Kline, and French, such as several combination medications including a mixture of dextroamphetamine and amobarbital (a barbiturate) sold under the tradename Dexamyl and, in the 1950s, an extended release capsule (the "Spansule").[4]
It quickly became apparent that dextroamphetamine and other amphetamines had a high potential for misuse, although they were not heavily controlled until 1970, when the Comprehensive Drug Abuse Prevention and Control Act was passed by the United States Congress. Dextroamphetamine, along with other sympathomimetics, was eventually classified as Schedule II, the most restrictive category possible for a drug with recognized medical use.[5]
Internationally, it has been available under the names AmfeDyn (Italy), Curban (US), Obetrol (Switzerland), Simpamina (Italy), Dexedrine (US & Canada), Dextropa (Portugal), and Stild (Spain).[6]