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Phenylpropanolamine
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Phenylpropanolamine (PPA) is a drug ingredient of the phenethylamine family used as a decongestant in prescription and nonprescription (over the counter) cough and cold, and sinus remedies, and some combination allergy medications. It is also present in an appetite suppressant. In veterinary medicine, it is used to control urinary incontinence in dogs.
In the United States, PPA is no longer sold without a prescription due to a somewhat increased risk of stroke in younger women.
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Encyclopedia
Phenylpropanolamine (PPA) is a drug ingredient of the phenethylamine family used as a decongestant in prescription and nonprescription (over the counter) cough and cold, and sinus remedies, and some combination allergy medications. It is also present in an appetite suppressant. In veterinary medicine, it is used to control urinary incontinence in dogs.
In the United States, PPA is no longer sold without a prescription due to a somewhat increased risk of stroke in younger women. In Europe, it is available by prescription and over-the-counter. In Canada, this drug ingredient was withdrawn from the market on May 31, 2001.
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. The former all are primary amines, the latter are secondary amines with a methyl group attached to the nitrogen.
Phenylpropanolamine was also used for the illicit synthesis of other stimulant drugs such as phenmetrazine and 4-methylaminorex, and since phenylpropanolamine was withdrawn from use in humans in the early 2000s (although it is still sold for some veterinary applications) it is now much less available, and this in turn has meant that phenmetrazine and 4-methylaminorex have largely disappeared from the illicit market.
Phenylpropanolamine can be made from cathinone.
Side effects
A scientific study 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.
A report from the Dept. of Psychiatry, F. Edward Hebert School of Medicine, Bethesda, Maryland in Pharmacopsychiatry states:
Legal status
In Europe, PPA is still available in prescription decongestants such as Rinexin
as well as over-the-counter medication such as Wick DayMed.
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. In 2005 the FDA removed phenylpropanolamine from over-the-counter sale. 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
Because of its potential use in amphetamine manufacture, it is controlled by the Combat Methamphetamine Epidemic Act of 2005. It is still available for use in dogs.
Available in India in the form of a combination tablet with Cetirizine as Alerid-D manufactured by Cipla.
See also
External links
- at www.FDA.gov
- By Kevin Sack and Alicia Mundy.Los Angeles Times, March 28, 2004.
- by David Michaels, Scientific American, June 2005
- by Richard Clapp, a case study at DefendingScience.org
- Description of widely circulated email using out-of-date information about Phenylpropanolamine.
- Use of Phenylpropanolamine in dogs.
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