Phenylpropanolamine
| Clinical data | |
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| Other names | PPA; Norephedrine; (1RS,2SR)-Phenylpropanolamine; dl-Norephedrine; (±)-Norephedrine; (1RS,2SR)-α-Methyl-β-hydroxyphenethylamine; (1RS,2SR)-β-Hydroxyamphetamine |
| AHFS/Drugs.com | Multum Consumer Information |
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| Routes of administration | By mouth |
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| Pharmacokinetic data | |
| Bioavailability | High[2] |
| Protein binding | 20%[3][2] |
| Metabolism | Minimal (3–4%)[3][5][2] |
| Metabolites | • Hippuric acid (~4%)[2][3] • 4-Hydroxynorephedrine (≤1%)[3][2] |
| Onset of action | Oral: 15–30 minutes[2][4] |
| Elimination half-life | 4 hours (range 3.7–4.9 hours)[2][4][5][6] |
| Duration of action | Oral: 3 hours[2][4] |
| Excretion | Urine: 90% (unchanged)[4][2] |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.035.349 |
| Chemical and physical data | |
| Formula | C9H13NO |
| Molar mass | 151.209 g·mol−1 |
| 3D model (JSmol) | |
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Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent used as a decongestant and appetite suppressant.[7][8][9][10] It was once common in prescription and over-the-counter cough and cold preparations. The medication is taken orally.[2][11]
Side effects of phenylpropanolamine include increased heart rate and blood pressure.[12][13][14][11] Rarely, PPA has been associated with hemorrhagic stroke.[10][15][12] PPA acts as a norepinephrine releasing agent, indirectly activating adrenergic receptors.[16][17][18] As such, it is an indirectly acting sympathomimetic.[16][17][18][9] It was once thought to act as a sympathomimetic with additional direct agonist action on adrenergic receptors, but this proved wrong.[16][17][18] Chemically, phenylpropanolamine is a substituted amphetamine and is closely related to ephedrine, pseudoephedrine, amphetamine, and cathinone.[19][20][21][10] It is usually a racemic mixture of the (1R,2S)- and (1S,2R)-enantiomers of β-hydroxyamphetamine and is also known as dl-norephedrine.[20][7][8]
Phenylpropanolamine was first synthesized around 1910 and its effects on blood pressure were characterized around 1930.[20][10] It was introduced as medicine by the 1930s.[22][10] It was withdrawn from many markets starting in 2000 after learning that it was associated with increased risk of hemorrhagic stroke.[22][10] It was previously available both over-the-counter and by prescription.[22][23][24][25] Phenylpropanolamine is available for both human and/or veterinary use in some countries.[23]
- ^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
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YoonBaeHong2007was invoked but never defined (see the help page). - ^ a b c Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
- ^ a b c Rothman RB, Baumann MH (December 2005). "Targeted screening for biogenic amine transporters: potential applications for natural products". Life Sci. 78 (5): 512–518. doi:10.1016/j.lfs.2005.09.001. PMID 16202429.
- ^ a b c Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, et al. (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates". J Pharmacol Exp Ther. 307 (1): 138–145. doi:10.1124/jpet.103.053975. PMID 12954796.
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Johnson1991was invoked but never defined (see the help page). - ^ Bravo EL (March 1988). "Phenylpropanolamine and other over-the-counter vasoactive compounds". Hypertension. 11 (3 Pt 2): II7–10. doi:10.1161/01.hyp.11.3_pt_2.ii7. PMID 3280497.
- ^ a b c Mersfelder TL (March 2001). "Phenylpropanolamine and stroke: the study, the FDA ruling, the implications". Cleve Clin J Med. 68 (3): 208–9, 213–9, 223. doi:10.3949/ccjm.68.3.208 (inactive 1 July 2025). PMID 11263849.
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