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Dextroamphetamine (Molecule of the Month for September 2007)

Dexedrine, Dextrostat, D-amphetamine, Dexamphetamine

Dextroamphetamine is the dextrorotary (D) stereoisomer of the amphetamine molecule, which can take two different forms. Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. Primarily, dextroamphetamine is used to treat attention deficit hyperactivity disorder (ADHD). In some localities it has replaced methylphenidate as the first-choice medication for ADHD, a role in which it is considered highly effective. It is also used as treatment of Narcolepsy, generally where non-pharmacological measures have proved insufficient, and occasionally it is prescribed for weight-loss in cases of extreme obesity. The U.S. Air Force uses dextroamphetamine as its "go-pill,", given to pilots on long missions to help them remain focused and alert. Other branches of the U.S. military (as well as the armed forces of other nations commonly use or have dispensed dextroamphetamine to troops to prevent or treat fatigue in combat situations.

Amphetamine was first synthesized under the chemical name "phenylisopropylamine" in Berlin, 1887 by the Romanian chemist Lazar Edeleanu. It was not widely marketed until 1932, when the pharmaceutical company Smith, Kline, and French (currently known as GlaxoSmithKline) introduced it in the form of the Benzedrine Inhaler, for combating cold symptoms. 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 Dexedrine tablets, under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. It quickly became apparent that Dexedrine and other amphetamines had a high potential for abuse, although they were not heavily controlled until 1970, when the Comprehensive Drug Abuse Prevention and Control Act was passed by the United States Congress. Dexedrine, along with other sympathomimetics, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses.

The English pop group Dexys Midnight Runners were named after Dexedrine, a brand of dextroamphetamine popularly used as a recreational drug among Northern Soul fans at the time. Along with Ritalin, illicit use of dextroamphetamine has been reported among students, both as a study aid, social aid, and for purely recreational purposes. According to the National Institute on Drug Abuse, 4% of American college students reported non-prescription stimulant use in 2004.

Formal Chemical Name (IUPAC)



Picture of Dextroamphetamine

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Dextroamphetamine structure
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Picture of Dextroamphetamine

C9 H13 N

Update by Karl Harrison
(Molecule of the Month for September 2007 )