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20-September-2008 09:55:56 - Phenylpropanolamine Pharmacology or the Pharmacology Portal may be able to help recruit one. If a more appropriate or portal exists, please adjust this template accordingly. 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 Chemical data Formula C9H13NO 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 ?US ℞-only Routes Oral Phenylpropanolamine PPA is a drug of the phenethylamine family used as a decongestant1 and also as 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 In Europe it is either only available by prescription or completely withdrawn from the market. Contents 1 Chemistry 2 Side effects 3 Legal status 4 See also 5 References 6 External links 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.citation needed The former all are primary amines, the latter are secondary amines with a methyl group attached to the nitrogen.citation needed 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synthesis of other stimulant drugs such as phenmetrazine and 4-methylaminorex, and since phenylpropanolamine was withdrawn from use in humans in the early 2000s although it is still sold for some veterinary applications it is now much less available, and this in turn has meant that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.citation needed Phenylpropanolamine can be made from cathinone.citation needed Side effects A scientific study2 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.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 Pharmacopsychiatry3 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 4 as well as over-the-counter medication such as Wick DayMed. In November 2000, the Food and Drug Administration FDA issued a public health advisory5 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.6 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 Substances7 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. See also Chlorphenamine phenethylamines Cathine ephedrine pseudoephedrine cathinone methcathinone amphetamine methamphetamine phenmetrazine 4-methylaminorex References ^ Flavahan NA April 2005. Phenylpropanolamine constricts mouse and human blood vessels by preferentially activating alpha2-adrenoceptors. J. Pharmacol. Exp. Ther. 313 1: 432-9. doi:10.1124/jpet.104.076653. PMID 15608085. ^ http://content.nejm.org/cgi/content/abstract/343/25/1826 Phenylpropanolamine and the Risk of Hemorrhagic Stroke, Kernan et al., 2000 N Engl J Med 343:1826-1832 ^ http://ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmedcmd=Retrievelist_uids=3060884 Psychiatric side effects attributed to phenylpropanolamine, Pharmacopsychiatry 1988 Jul; 214:171-81 ^ http://www.fass.se/LIF/produktfakta/artikel_produkt.jsp?NplID=19790406000053DocTypeID=3UserTypeID=0, Rinexin in Farmaceutiska Specialiteter i Sverige - the Swedish official drug catalog.in Swedish ^ http://www.fda.gov/cder/drug/infopage/ppa/advisory.htm Food and Drug Administration Public Health Advisory, Safety of Phenylpropanolamine, www.FDA.gov ^ http://www.fda.gov/cder/drug/infopage/ppa/ FDA moves PPA from OTC ^ http://www.unodc.org/unodc/en/document_1999-12-21_1.html 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 Phenylpropanolamine Information Page at www.FDA.gov A Dose of Denial: How drug makers sought to keep popular cold and diet remedies on store shelves after their own study linked them to strokes. By Kevin Sack and Alicia Mundy.Los Angeles Times, March 28, 2004. Doubt Is Their Product by David Michaels, Scientific American, June 2005 Phenylpropanolamine by Richard Clapp, a case study at DefendingScience.org Widely Circulated Email About Phenylpropanolamine Description of widely circulated email using out-of-date information about Phenylpropanolamine. Treatment of urethral sphincter mechanism incompetence in 11 bitches with a sustained-release formulation of phenylpropanolamine hydrochloride Use of Phenylpropanolamine in dogs. v d e Adrenergic agonists models/most important in CAPS α α1 METHOXAMINE - Methylnorepinephrine - Oxymetazoline - PHENYLEPHRINE - Metaraminol α2 4-NEMD - CLONIDINE - Guanfacine - Guanabenz - Guanoxabenz - Guanethidine - Xylazine - METHYLDOPA - Apraclonidine - Brimonidine - Detomidine - Dexmedetomidine - Lofexidine - Romifidine - Tizanidine - Xylometazoline Undetermined/ unsorted Amidephrine - Amitraz - Anisodamine - Ergotamine - Indanidine - Medetomidine - Mephentermine - Midodrine - Mivazerol - Naphazoline - Norfenefrine - Octopamine - Phenylpropanolamine - Rilmenidine - Synephrine - Talipexole - Tetrahydrozoline - Xylometazoline β β1 DOBUTAMINE - Dopamine - Denopamine - Xamoterol β2 Short acting β2-agonists: SALBUTAMOL/Levosalbutamol - Fenoterol - TERBUTALINE - Pirbuterol - Procaterol - Bitolterol - Rimiterol - Carbuterol - Tulobuterol - Reproterol - Dopexamine Long acting β2-agonists LABA: Arformoterol - Bambuterol - Clenbuterol - Formoterol - Salmeterol Orciprenaline/metaproterenol - Ritodrine - Hexoprenaline - Indacaterol β3 Amibegron - Solabegron Undetermined/ unsorted Arbutamine - Befunolol - Isoxsuprine - Nylidrin - Oxyfedrine - Prenalterol - Ractopamine - Bromoacetylalprenololmenthane - Broxaterol - Cimaterol - Higenamine - Mabuterol - Methoxyphenamine - Tretoquinol - Zinterol Nonselective β ISOPRENALINE/ISOPROTERENOL α and β Epinephrine α1+2, β1+2 - Norepinephrine α1+2, β1 - Cirazoline - Etilefrine Indirect/ mixed Indirect presynaptic norepinephrine release: Amphetamine - Tyramine Mixed: Ephedrine - Pseudoephedrine Cocaine see also monoamine oxidase inhibitor v d e Decongestants and other nasal preparations R01 Topical Sympathomimetics, plain Cyclopentamine - Ephedrine - Phenylephrine - Oxymetazoline - Tetryzoline - Xylometazoline - Naphazoline - Tramazoline - Metizoline - Tuaminoheptane - Fenoxazoline - Tymazoline - Epinephrine Antiallergic agents, excluding corticosteroids Spaglumic acid histamine antagonists Levocabastine, Antazoline, Thonzylamine mast cell stabilizer some are also antihistamines Cromoglicic acid, Nedocromil, Azelastine, Olopatadine Corticosteroids Beclometasone - Prednisolone - Dexamethasone - Flunisolide - Budesonide - Betamethasone - Tixocortol - Fluticasone - Mometasone furoate - Triamcinolone - Ciclesonide Other nasal preparations Calcium hexamine thiocyanate - Retinol - Ipratropium bromide - Ritiometan - Mupirocin - Hexamidine - Framycetin Systemic use: Sympathomimetics Phenylpropanolamine - Pseudoephedrine - Phenylephrine Retrieved from http://en..org/wiki/Phenylpropanolamine Categories: Alcohols | Alkaloids | Amphetamines | Anorectics | Decongestants | Sympathomimetic amines | Withdrawn drugs | DEA List I chemicalsHidden categories: Pharmacology articles needing expert attention | Articles needing expert attention | Pages needing expert attention | All articles with statements | Articles with statements since June 2008 | Articles with statements since July 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Norsk bokmål Polski Svenska 中文 This page was last modified on 15 August 2008, at 12:05
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