Phenylpropanolamine

Phenylpropanolamine
RS-Norephedrin
Ball-and-stick model of the phenylpropanolamine molecule
Clinical data
Trade namesMany[1][2]
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[4]
Protein binding20%[5][4]
MetabolismMinimal (3–4%)[5][7][4]
Metabolites• Hippuric acid (~4%)[4][5]
• 4-Hydroxynorephedrine (≤1%)[5][4]
Onset of actionOral: 15–30 minutes[4][6]
Elimination half-life4 (3.7–4.9) hours[4][6][7][8]
Duration of actionOral: 3 hours[4][6]
ExcretionUrine: 90% (unchanged)[6][4]
Identifiers
  • (1RS,2SR)-2-amino-1-phenylpropan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.349 Edit this at Wikidata
Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
3D model (JSmol)
  • O[C@H](c1ccccc1)[C@@H](N)C
  • 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 checkY
  • Key:DLNKOYKMWOXYQA-CBAPKCEASA-N checkY
  (verify)

Phenylpropanolamine (PPA), sold under many brand names, is a sympathomimetic agent which is used as a decongestant and appetite suppressant.[9][1][10][11] It was previously commonly used in prescription and over-the-counter cough and cold preparations. The medication is taken by mouth.[4][12]

Side effects of PPA include increased heart rate and blood pressure, among others.[13][14][15][12] Rarely, PPA has been associated with hemorrhagic stroke.[11][16][13] PPA acts as a norepinephrine releasing agent, thereby indirectly activating adrenergic receptors.[17][18][19] As such, it is an indirectly acting sympathomimetic.[17][18][19][10] It was previously thought to act as a mixed acting sympathomimetic with additional direct agonist actions on adrenergic receptors, but this proved not to be the case.[17][18][19] Chemically, PPA is a substituted amphetamine and is closely related to ephedrine, pseudoephedrine, amphetamine, and cathinone.[20][21][22][11] It is most commonly a racemic mixture of the (1R,2S)- and (1S,2R)-enantiomers of β-hydroxyamphetamine and is also known as dl-norephedrine.[21][9][1]

PPA was first synthesized around 1910 and its effects on blood pressure were first characterized around 1930.[21][11] It was introduced for medical use by the 1930s.[23][11] The medication was withdrawn from many markets starting in 2000 following findings that it was associated with increased risk of hemorrhagic stroke.[23][11] It was previously available both over-the-counter and by prescription.[23][2][24][25] PPA remains available for medical and/or veterinary use in some countries.[2]

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  2. ^ a b c Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  3. ^ 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.
  4. ^ 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).
  5. ^ a b c d Cite error: The named reference ChuaBenrimojTriggs1989 was invoked but never defined (see the help page).
  6. ^ a b c d Cite error: The named reference BouchardWeberGeiger2002 was invoked but never defined (see the help page).
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  8. ^ "Phenylpropanolamine: Uses, Interactions, Mechanism of Action". DrugBank Online. 29 June 2018. Retrieved 1 August 2024.
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  10. ^ a b Cite error: The named reference MortonHall2012 was invoked but never defined (see the help page).
  11. ^ 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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  17. ^ 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.
  18. ^ 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.
  19. ^ 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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  22. ^ 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.
  23. ^ 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. PMID 11263849.
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