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Encyclopedia > Phenylpropanolamine
Phenylpropanolamine chemical structure
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. weight 151.206 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life 2.1 to 3.4 hours.
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Information_icon. ... Image File history File links Phenylpropanolamine. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Overview of the citric acid cycle The citric acid cycle, one of the central metabolic pathways in aerobic organisms. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

Phenylpropanolamine (PPA) is a drug of the phenethylamine family used as a decongestant and also as an appetite suppressant. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Oral medication A medication is a licenced drug taken to cure or reduce symptoms of an illness or medical condition. ... Phenethylamine (β-Phenylethylamine) is an alkaloid and monoamine. ... A decongestant is a broad class of drugs designed to symptomatically treat ailments affecting the respiratory system. ... Anorectics, anorexigenics or appetite suppressants, are substances which reduce the desire to eat (anorectic, from the Greek an- = not and oreg- = extend, reach). Used on a short term basis clinically to treat obesity, some appetite suppressants are also available over the counter. ...

Contents

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. Optical isomerism is a form of isomerism (specifically stereoisomerism) whereby the different 2 isomers are the same in every way except being non-superimposable mirror images* of each other. ... This article is about logical nor Nór. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... This article is about logical nor Nór. ... Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. ... Cathine (β-hydroxyamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat). ... Stimulants are drugs that increase alertness and wakefulness. ... Divisions Green algae Chlorophyta Charophyta Land plants (embryophytes) Non-vascular plants (bryophytes) Marchantiophyta - liverworts Anthocerotophyta - hornworts Bryophyta - mosses Vascular plants (tracheophytes) †Rhyniophyta - rhyniophytes †Zosterophyllophyta - zosterophylls Lycopodiophyta - clubmosses †Trimerophytophyta - trimerophytes Pteridophyta - ferns and horsetails Seed plants (spermatophytes) †Pteridospermatophyta - seed ferns Pinophyta - conifers Cycadophyta - cycads Ginkgophyta - ginkgo Gnetophyta - gnetae Magnoliophyta - flowering plants... Binomial name Catha edulis (Vahl) Forssk. ... World map exhibiting the location of Europe. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecule. ...


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. Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Semi-accurate illustration of a redox reaction Redox reactions include all chemical processes in which atoms have their oxidation number (oxidation state) changed. ... Methamphetamine (methylamphetamine or desoxyephedrine), popularly shortened to meth, is a psychostimulant drug used primarily for recreational purposes, but also prescribed for attention-deficit hyperactivity disorder or narcolepsy under the brand name Desoxyn. ... Amphetamine (alpha-methyl-phenethylamine), also known as speed whiffles, is a stimulant, and club drug, used to diminish the appetite, control weight, and treat disorders including narcolepsy and attention-deficit hyperactivity disorder. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... To meet Wikipedias quality standards, this article or section may require cleanup. ...


Phenylpropanolamine can be made from cathinone. Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ...


Side effects

A scientific study[1] 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.[citation needed] Reports of cases of hemorrhagic strokes in PPA users had been circulating since the 1970s. Hemorrhagic stroke, or cerebral hemorrhage is a form of stroke that occurs when a blood vessel in the brain ruptures. ... 1999 (MCMXCIX) was a common year starting on Friday, and was designated the International Year of Older Persons by the United Nations. ...


A report from the Dept. of Psychiatry, F. Edward Hebert School of Medicine, Bethesda, Maryland in Pharmacopsychiatry[2] 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 control

In November 2000, the Food and Drug Administration (FDA) issued a public health advisory[3] 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.[4] 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[5] This article is about the year 2000. ... The Food and Drug Administration (FDA) is an agency of the United States Department of Health and Human Services and is responsible for regulating food (humans and animal), dietary supplements, drugs (human and animal), cosmetics, medical devices (human and animal) and radiation emitting devices (including non-medical devices), biologics, and... 2005 (MMV) was a common year starting on Saturday of the Gregorian calendar. ... This article is about the year 2000. ... At the presiding table, from left to right: Mr. ... Phenylpropanolamine (PPA) is a drug of the phenethylamine family used in bronchial and nasal decongestants, and also as an appetite suppressant. ... United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances Opened for signature December 20, 1988[1] at Vienna Entered into force November 11, 1990[2] Conditions for entry into force 20 ratifications Parties 170[3] The 1988 United Nations Convention Against Illicit Traffic in Narcotic Drugs and...


Because of its potential use in methamphetamine manufacture, it is controlled by the Combat Methamphetamine Epidemic Act of 2005. Methamphetamine (methylamphetamine or desoxyephedrine), popularly shortened to meth, is a psychostimulant drug used primarily for recreational purposes, but also prescribed for attention-deficit hyperactivity disorder or narcolepsy under the brand name Desoxyn. ... The Combat Methamphetamine Epidemic Act of 2005 (CMEA) was signed into United States law on March 9, 2006 to regulate, among other things, retail over-the-counter sales of ephedrine, pseudoephedrine, and phenylpropanolamine products. ...


See also

Phenethylamine (β-Phenylethylamine) is an alkaloid and monoamine. ... Cathine (β-hydroxyamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat). ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... To meet Wikipedias quality standards, this article or section may require cleanup. ... Amphetamine (alpha-methyl-phenethylamine), also known as speed whiffles, is a stimulant, and club drug, used to diminish the appetite, control weight, and treat disorders including narcolepsy and attention-deficit hyperactivity disorder. ... Methamphetamine (methylamphetamine or desoxyephedrine), popularly shortened to meth, is a psychostimulant drug used primarily for recreational purposes, but also prescribed for attention-deficit hyperactivity disorder or narcolepsy under the brand name Desoxyn. ...

References

  1. ^ 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
  2. ^ http://ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&list_uids=3060884 Psychiatric side effects attributed to phenylpropanolamine, Pharmacopsychiatry 1988 Jul; 21(4):171-81
  3. ^ http://www.fda.gov/cder/drug/infopage/ppa/advisory.htm Food and Drug Administration Public Health Advisory, "Safety of Phenylpropanolamine", www.FDA.gov
  4. ^ http://www.fda.gov/cder/drug/infopage/ppa/ FDA moves PPA from OTC
  5. ^ 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

  • Links to external chemical sources

  Results from FactBites:
 
Phenylpropanolamine (666 words)
In order to understand how phenylpropanolamine works in the body, it is important to understand some background regarding the “autonomic nervous system.” The autonomic nervous system can be thought of as the “automatic” nervous system in that it controls physiologic functions that one is not aware of.
Phenylpropanolamine is also a potent decongestant and is a common cold remedy ingredient.
Phenylpropanolamine acts by causing the release of a hormone and neurotransmitter called “norepinephrine.” With chronic use, it is possible to deplete the body’s stores of norepinephrine and the patient will appear to become “resistent” to the effects of the drug.
phenylpropanolamine - [Medication] (1200 words)
Phenylpropanolamine has been associated with an increased risk of hemorrhagic stroke (bleeding into the brain or into tissue surrounding the brain) in women.
Phenylpropanolamine is used to treat the congestion associated with allergies, hay fever, sinus irritation, and the common cold.
Phenylpropanolamine also causes a decrease in appetite and is used in some over-the-counter diet aids.
  More results at FactBites »

 
 

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