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Phenylpropanolamine (PPA) is a drug of the phenethylamine family used as a decongestant and also as an appetite suppressant.

Chemistry

There are four optical isomers of phenylpropanolamine: d- and l-norephedrine, and d- and l-norpseudoephedrine. D-norpseudoephedrine is also known as cathine, and occurs naturally in the stimulant plant Catha edulis (khat). This isomer is commonly used in European medications described as "phenylpropanolamine", whereas in the United States a racemic mixture of d,l-norephedrine is usual.

Just as ephedrine is chemically reduced into methamphetamine, phenylpropanolamine can be chemically reduced into amphetamine. Molecularly, phenylpropanolamine is to ephedrine, just as amphetamine is to methamphetamine, and as cathinone is to methcathinone.

Phenylpropanolamine can be made from cathinone.

Effects

A scientific study (Kernan et al. 2000) found an increased risk of hemorrhagic stroke in women who used phenylpropanolamine, although it is not clear which isomer is to blame. A study at the Yale University School of Medicine in 1999 had produced similar results. Reports of cases of hemorrhagic strokes in PPA users had been circulating since the 1970s.

In November 2000, the Food and Drug Administration (FDA) issued a public health advisory against the use of the drug In this advisory, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine. The agency estimates that PPA caused between 200 and 500 strokes a year among 18-to-49-year-old users. An item on the agenda of the 2000 Commission on Narcotic Drugs session called for including norephedrine in Table I of United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[http://www.unodc.org/unodc/en/document_1999-12-21_1.html.

See also

• phenethylamines
• Cathine
• ephedrine
• pseudoephedrine
• cathinone
• methcathinone
• amphetamine
• methamphetamine

References

• Implementation of the international drug control treaties: changes in the scope of control of substances, Commission on Narcotic Drugs, Forty-third session, Vienna, 6-15 March 2000.

External links

• Kernan et al., Phenylpropanolamine and the Risk of Hemorrhagic Stroke 2000 N Engl J Med 343:1826-1832
• FDA phenylpropanolamine Information Page
• Doubt Is Their Product by David Michaels, Scientific American, June 2005
• Phenylpropanolamine by Richard Clapp, a case study at DefendingScience.org

Alcohols | Alkaloids | Amphetamines | Anorectics | Decongestants | Sympathomimetic amines | Withdrawn drugs

Norephedrin | Phénylpropanolamine | Fenylopropanolamina | 苯丙醇胺