Phenylpropanolamine: Wikis

  
  

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Phenylpropanolamine
Systematic (IUPAC) name
(1R,2S)-2-amino-1-phenyl-propan-1-ol
Identifiers
CAS number 14838-15-4
ATC code R01BA01
PubChem 26934
DrugBank APRD00457
ChemSpider 25082
Chemical data
Formula C 9H13NO 
Mol. mass 151.206 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life 2.1 to 3.4 hours.
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status GSL (UK) ? (US) ℞-only
Routes Oral
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Phenylpropanolamine (PPA; Accutrim, Dexatrim), also known as norephedrine and oxyamphetamine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which is used as a stimulant, decongestant, and anorectic agent.[1][2] It is commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to control urinary incontinence in dogs under trade names Propalin and Proin.

In the United States, PPA is no longer sold without a prescription due to a proposed increased risk of stroke in younger women. In Europe, however, it is still available by both prescription and over-the-counter. In Canada, it was withdrawn from the market on May 31, 2001.[2]

Contents

Pharmacology

PPA acts as a potent and selective releasing agent of norepinephrine and epinephrine, or as a norepinephrine releasing agent (NRA). It also acts as a dopamine releasing agent (DRA) to a lesser extent.

Chemistry

There are four optical isomers of PPA: dextro- and levo- norephedrine, and dextro- and levo- norpseudoephedrine. d-Norpseudoephedrine is also known as cathine, and occurs naturally in Catha edulis ("Khat").

Just as ephedrine can be chemically reduced into methamphetamine, PPA may be chemically reduced into amphetamine. Structurally, PPA is to ephedrine, just as amphetamine is to methamphetamine, and as cathinone is to methcathinone. PPA can also be used in the synthesis of phenmetrazine and 4-methylaminorex.

Synthesis is a standard Henry reaction between benzaldehyde and nitroethane, although care is taken not to dehydrate the alcohol. Reduction is usually done with a mild agent including zinc. The products of this step can be vacuum distilled.

Side Effects

A scientific study[3] found an increased risk of hemorrhagic stroke in women who used PPA, 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.[1] 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[4] states:

We have reviewed 37 cases (published in North America and Europe since 1960) that received diagnoses of acute mania, paranoid schizophrenia, and organic psychosis and that were attributed to PPA product ingestion. Of the 27 North American case reports, more reactions followed the ingestion of combination products than preparations containing PPA alone; more occurred after ingestion of over-the-counter products than those obtained by prescription or on-the-street; and more of the cases followed ingestion of recommended doses than overdoses.
Failure to recognize PPA as an etiological agent in the onset of symptoms usually led to a diagnosis of schizophrenia or mania, lengthy hospitalization, and treatment with substantial doses of neuroleptics or lithium.

Legal Status

In Europe, PPA is still available in prescription decongestants such as Rinexin [5], as well as over-the-counter medications such as Wick DayMed.

In the United Kingdom, PPA is available in many 'all in one' cough and cold medications which usually also feature paracetamol or another analgesic and caffeine. It can also be purchased on its own. It is classed as GSL (general sale license) and is completely derestricted, therefore saleable by any shop.

In the United States, the Food and Drug Administration (FDA) issued a public health advisory[6] against the use of the drug in November 2000. In this advisory, the FDA requested that all drug companies discontinue marketing products containing PPA. The agency estimates that PPA caused between 200 and 500 strokes per year among 18-to-49-year-old users. In 2005, the FDA removed PPA from over-the-counter sale.[7] Because of its potential use in amphetamine manufacture, it is controlled by the Combat Methamphetamine Epidemic Act of 2005. It is still available for veterinary use in dogs, however, as a treatment for urinary incontinence.

Internationally, an item on the agenda of the 2000 Commission on Narcotic Drugs session called for including PPA in Table I of United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances[8]

PPA is available in India in the form of a combination tablet with cetirizine as Alerid-D, which is manufactured by Cipla. It is also present in popular cold and flu treatment medicine D-Cold Total available over the counter.

See also

References

External links








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