Phenylpropanolamine

Phenylpropanolamine
Clinical data
Other namesPPA; Norephedrine; (1RS,2SR)-Phenylpropanolamine; dl-Norephedrine; (±)-Norephedrine; (1RS,2SR)-α-Methyl-β-hydroxyphenethylamine; (1RS,2SR)-β-Hydroxyamphetamine
AHFS/Drugs.comMultum Consumer Information
Pregnancy
category
  • AU: B2
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh[2]
Protein binding20%[3][2]
MetabolismMinimal (3–4%)[3][5][2]
Metabolites• Hippuric acid (~4%)[2][3]
4-Hydroxynorephedrine (≤1%)[3][2]
Onset of actionOral: 15–30 minutes[2][4]
Elimination half-life4 hours (range 3.7–4.9 hours)[2][4][5][6]
Duration of actionOral: 3 hours[2][4]
ExcretionUrine: 90% (unchanged)[4][2]
Identifiers
IUPAC name
  • (1RS,2SR)-2-amino-1-phenylpropan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.349
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
3D model (JSmol)
SMILES
  • O[C@H](c1ccccc1)[C@@H](N)C
InChI
  • InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1 Y
  • Key:DLNKOYKMWOXYQA-CBAPKCEASA-N Y
  (verify)

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on blood pressure were characterized around 1930.[20][10] It was introduced as medicine by the 1930s.[22][10] It was withdrawn from many markets starting in 2000 after learning that it was associated with increased risk of hemorrhagic stroke.[22][10] It was previously available both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]

  1. ^ 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.
  2. ^ a b c d e f g h i j Cite error: The named reference KanferDowseVuma1993 was invoked but never defined (see the help page).
  3. ^ a b c d Cite error: The named reference ChuaBenrimojTriggs1989 was invoked but never defined (see the help page).
  4. ^ a b c d Cite error: The named reference BouchardWeberGeiger2002 was invoked but never defined (see the help page).
  5. ^ a b Cite error: The named reference GentileFridaySkoner2000 was invoked but never defined (see the help page).
  6. ^ "Phenylpropanolamine: Uses, Interactions, Mechanism of Action". DrugBank Online. 29 June 2018. Retrieved 1 August 2024.
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  8. ^ a b Cite error: The named reference IndexNominum2000 was invoked but never defined (see the help page).
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  10. ^ a b c d e f Ioannides-Demos LL, Proietto J, Tonkin AM, McNeil JJ (2006). "Safety of drug therapies used for weight loss and treatment of obesity". Drug Saf. 29 (4): 277–302. doi:10.2165/00002018-200629040-00001. PMID 16569079.
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  16. ^ 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.
  17. ^ 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.
  18. ^ 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.
  19. ^ Cite error: The named reference LemkeWilliams2008 was invoked but never defined (see the help page).
  20. ^ a b c Cite error: The named reference Johnson1991 was invoked but never defined (see the help page).
  21. ^ 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.
  22. ^ 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.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
  23. ^ a b Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
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