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Pseudoephedrine

From Wikipedia
(+)-pseudoephedrine
type of chemical entity
Subclass of1-phenylpropan-2-amine alkaloid, (1R)-2-(methylamino)-1-phenyl-1-propanol Edit
Get useMedication Edit
Stereoisomer of(−)-pseudoephedrine, (−)-ephedrine, (+)-ephedrine Edit
Chemical formulaC₁₀H₁₅NO Edit
Canonical SMILESCC(C(C1=CC=CC=C1)O)NC Edit
Isomeric SMILESC[C@@H]([C@H](C1=CC=CC=C1)O)NC Edit
World Health Organisation international non-proprietary namepseudoephedrine Edit
Medical condition treatedsinusitis, asthma, common cold, nasopharyngitis Edit
Physically dey interact plusSolute carrier family 6 member 2 Edit
Pregnancy categoryAustralian pregnancy category B2, US pregnancy category C Edit
Subject has rolealpha-adrenergic agonist, adrenergic beta-agonists, bronchodilator, decongestant Edit

Pseudoephedrine, dem sell under de brand name Sudafed among odas, be a sympathomimetic medication wich be used as a decongestant to treat nasal congestion.[1][2][3] Na dem sanso dey use am off-label give certain oda indications, like treatment of low blood pressure.[4][5][6] At higher doses, e fi produce various additional effects wey dey include stimulant,[1][7] appetite suppressant,[8] den performance-enhancing effects.[9][10] In relation to dis, na non-medical use of pseudoephedrine be encountered.[1][7][8][9][10] Dem dey take de medication by mouth.[1][3]

Side effects of pseudoephedrine dey include insomnia, elevated heart rate, increased blood pressure, restlessness, dizziness, anxiety, den dry mouth, among odas.[1][3][11][12] Rarely, na pseudoephedrine be associated plus serious cardiovascular complications like heart attack den hemorrhagic stroke.[5][8][13] Sam people fi be more sensitive to ein cardiovascular effects.[1][12] Pseudoephedrine dey act as a norepinephrine releasing agent, thereby indirectly dey activate adrenergic receptors.[1][3][14][15] As such, e be an indirectly acting sympathomimetic.[1][3][14][15] Pseudoephedrine significantly dey cross into de brain, buh e get sam peripheral selectivity secof ein hydrophilicity.[15][16] Chemically, pseudoephedrine be a substituted amphetamine wey e be closely related to ephedrine, phenylpropanolamine, den amphetamine.[1][2][3] E be de (1S,2S)-enantiomer of β-hydroxy-N-methylamphetamine.[17]

Along plus ephedrine, pseudoephedrine dey occur naturally insyd ephedra, wich na e be used for thousands of years insyd traditional Chinese medicine.[2][18] Na e first be isolated from ephedra insyd 1889.[2][18][19] Subsequent to ein synthesis insyd de 1920s, na dem introduce pseudoephedrine for medical use as a decongestant.[2] Pseudoephedrine widely be available over-the-counter (OTC) insyd both single-drug den combination preparations.[2][3][12][20] Na availability of pseudoephedrine be restricted starting insyd 2005 as e fi be used to synthesize methamphetamine.[2][3] Na phenylephrine replace pseudoephedrine insyd chaw over-the-counter oral decongestant products.[3] However, oral phenylephrine dey appear to be ineffective as a decongestant.[21][22] Insyd 2023, na pseudoephedrine be de 292nd most commonly prescribed medication insyd de United States, plus more dan 400,000 prescriptions.[23][24] Insyd 2023, na de combination plus brompheniramine den dextromethorphan be de 281st most commonly prescribed medication insyd de United States, plus more dan 700,000 prescriptions.[23][25] Insyd 2023, na de combination plus loratadine be de 300th most commonly prescribed medication insyd de United States, plus more dan 400,000 prescriptions.[26][27]

References

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  1. 1 2 3 4 5 6 7 8 9 Głowacka K, Wiela-Hojeńska A (May 2021). "Pseudoephedrine—Benefits and Risks". Int J Mol Sci. 22 (10): 5146. doi:10.3390/ijms22105146. PMC 8152226. PMID 34067981.
  2. 1 2 3 4 5 6 7 Laccourreye O, Werner A, Giroud JP, Couloigner V, Bonfils P, Bondon-Guitton E (February 2015). "Benefits, limits and danger of ephedrine and pseudoephedrine as nasal decongestants". Eur Ann Otorhinolaryngol Head Neck Dis. 132 (1): 31–34. doi:10.1016/j.anorl.2014.11.001. PMID 25532441.
  3. 1 2 3 4 5 6 7 8 9 Eccles R (January 2007). "Substitution of phenylephrine for pseudoephedrine as a nasal decongeststant. An illogical way to control methamphetamine abuse". British Journal of Clinical Pharmacology. 63 (1): 10–14. doi:10.1111/j.1365-2125.2006.02833.x. PMC 2000711. PMID 17116124.
  4. ↑ Freeman R, Kaufmann H (2007). "Disorders of Orthostatic Tolerance—Orthostatic Hypotension, Postural Tachycardia Syndrome, and Syncope". Continuum: Lifelong Learning in Neurology. 13 (6): 50–88. doi:10.1212/01.CON.0000299966.05395.6c. ISSN 1080-2371.
  5. 1 2 Van Berkel MA, Fuller LA, Alexandrov AW, Jones GM (2015). "Methylene blue, midodrine, and pseudoephedrine: a review of alternative agents for refractory hypotension in the intensive care unit". Crit Care Nurs Q. 38 (4): 345–358. doi:10.1097/CNQ.0000000000000086. PMID 26335214.
  6. ↑ Fedorowski A (April 2019). "Postural orthostatic tachycardia syndrome: clinical presentation, aetiology and management". J Intern Med. 285 (4): 352–366. doi:10.1111/joim.12852. PMID 30372565.
  7. 1 2 Głowacka K, Wiela-Hojeńska A (May 2021). "Pseudoephedrine—Benefits and Risks". Int J Mol Sci. 22 (10): 5146. doi:10.3390/ijms22105146. PMC 8152226. PMID 34067981.
  8. 1 2 3 Munafò A, Frara S, Perico N, Di Mauro R, Cortinovis M, Burgaletto C, Cantarella G, Remuzzi G, Giustina A, Bernardini R (December 2021). "In search of an ideal drug for safer treatment of obesity: The false promise of pseudoephedrine". Rev Endocr Metab Disord. 22 (4): 1013–1025. doi:10.1007/s11154-021-09658-w. PMC 8724077. PMID 33945051.
  9. 1 2 Trinh KV, Kim J, Ritsma A (2015). "Effect of pseudoephedrine in sport: a systematic review". BMJ Open Sport Exerc Med. 1 (1) e000066. doi:10.1136/bmjsem-2015-000066. PMC 5117033. PMID 27900142.
  10. 1 2 Gheorghiev MD, Hosseini F, Moran J, Cooper CE (October 2018). "Effects of pseudoephedrine on parameters affecting exercise performance: a meta-analysis". Sports Med Open. 4 (1) 44. doi:10.1186/s40798-018-0159-7. PMC 6173670. PMID 30291523.
  11. ↑ Taverner D, Latte J (January 2007). Latte GJ (ed.). "Nasal decongestants for the common cold". Cochrane Database Syst Rev (1) CD001953. doi:10.1002/14651858.CD001953.pub3. PMID 17253470.
  12. 1 2 3 Salerno SM, Jackson JL, Berbano EP (2005). "Effect of oral pseudoephedrine on blood pressure and heart rate: a meta-analysis". Arch Intern Med. 165 (15): 1686–1694. doi:10.1001/archinte.165.15.1686. PMID 16087815.
  13. ↑ Van Berkel MA, Fuller LA, Alexandrov AW, Jones GM (2015). "Methylene blue, midodrine, and pseudoephedrine: a review of alternative agents for refractory hypotension in the intensive care unit". Crit Care Nurs Q. 38 (4): 345–358. doi:10.1097/CNQ.0000000000000086. PMID 26335214.
  14. 1 2 Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA (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.
  15. 1 2 3 O'Donnell SR (March 1995). "Sympathomimetic vasoconstrictors as nasal decongestants". Med J Aust. 162 (5): 264–267. doi:10.5694/j.1326-5377.1995.tb139882.x. PMID 7534374.
  16. ↑ Bouchard R, Weber AR, Geiger JD (July 2002). "Informed decision-making on sympathomimetic use in sport and health". Clin J Sport Med. 12 (4): 209–224. doi:10.1097/00042752-200207000-00003. PMID 12131054.
  17. ↑ "Pseudoephedrine". PubChem. Retrieved 25 July 2024.
  18. 1 2 Abourashed EA, El-Alfy AT, Khan IA, Walker L (August 2003). "Ephedra in perspective--a current review". Phytother Res. 17 (7): 703–712. doi:10.1002/ptr.1337. PMID 12916063.
  19. ↑ Chen KK, Kao CH (1926). "Ephedrine and Pseudoephedrine, their Isolation, Constitution, Isomerism, Properties, Derivatives and Synthesis. (with a Bibliography) **The expense of this work has been defrayed by a part of a grant from the Committee on Therapeutic Research, Council on Pharmacy and Chemistry, American Medical Association". The Journal of the American Pharmaceutical Association (1912). 15 (8): 625–639. doi:10.1002/jps.3080150804.
  20. ↑ "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Food and Drug Administration. Archived from the original on 4 November 2016. Retrieved 14 July 2024.
  21. ↑ Hatton RC, Hendeles L (March 2022). "Why Is Oral Phenylephrine on the Market After Compelling Evidence of Its Ineffectiveness as a Decongestant?". Ann Pharmacother. 56 (11): 1275–1278. doi:10.1177/10600280221081526. PMID 35337187. S2CID 247712448.
  22. ↑ Hendeles L, Hatton RC (July 2006). "Oral phenylephrine: an ineffective replacement for pseudoephedrine?". J Allergy Clin Immunol. 118 (1): 279–280. doi:10.1016/j.jaci.2006.03.002. PMID 16815167.
  23. 1 2 "The Top 300 of 2023". ClinCalc. Archived from the original on 17 August 2025. Retrieved 17 August 2025.
  24. ↑ "Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  25. ↑ "Brompheniramine; Dextromethorphan; Pseudoephedrine Drug Usage Statistics, United States, 2014 - 2023". ClinCalc. Retrieved 17 August 2025.
  26. ↑ "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
  27. ↑ "Loratadine; Pseudoephedrine Drug Usage Statistics, United States, 2013 - 2023". ClinCalc. Retrieved 20 August 2025.
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