Pseudoephedrine

Pseudoephedrine
Clinical data
Pronunciation	/ˌsuːdoʊ.ɪˈfɛdrɪn, -ˈɛfɪdriːn/
Trade names	Afrinol, Sudafed, Sinutab, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682619
License data	EU EMA: by pseudoephedrine sulfate; US DailyMed: Pseudoephedrine;
Pregnancy; category	AU: B2; ;
Routes of; administration	By mouth
ATC code	R01BA02 (WHO) ;
Legal status
Legal status	AU: S3 (Pharmacist only) Largely tracked nationwide via “Project STOP” to avoid purchases in large quantities. Use of Project STOP is mandatory in all states and territories except Victoria and Tasmania; BR: Class D1 (Drug precursors); CA: OTC Removed from the NDS in 2024, for both combination and single ingredient preparations, on 1 Mar & 10 Jun 2024, respectively.; UK: P (Pharmacy medicines); US: OTC;
Pharmacokinetic data
Bioavailability	~100%
Metabolism	10–30% liver
Elimination half-life	4.3–8 hours
Excretion	43–96% kidney
Identifiers
	IUPAC name (S,S)-2-methylamino-1-phenylpropan-1-ol;
CAS Number	90-82-4 ;
PubChem CID	7028;
DrugBank	DB00852 ;
ChemSpider	6761 ;
UNII	7CUC9DDI9F;
KEGG	D08449 ;
ChEBI	CHEBI:51209 ;
ChEMBL	ChEMBL1590 ;
CompTox Dashboard (EPA)	DTXSID0023537 ;
ECHA InfoCard	100.001.835
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@@H](c1ccccc1)[C@@H](NC)C;
	InChI InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1 ; Key:KWGRBVOPPLSCSI-WCBMZHEXSA-N ;
	(verify)

Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant,^[7] as a stimulant, or as a wakefulness-promoting agent^[8] in higher doses.^[9]

It was first characterized in 1889 by the German chemists Ladenburg and Oelschlägel, who used a sample that had been isolated from Ephedra vulgaris by the Merck pharmaceutical corporation of Darmstadt, Germany.^[10] The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in over-the-counter preparations, either as a single ingredient or (more commonly) in a fixed-dose combination with one or more additional active ingredients such as antihistamines, guaifenesin, dextromethorphan, paracetamol (acetaminophen), or an NSAID (such as aspirin or ibuprofen).

^ "Project STOP A Pharmacy Guild Initiative, May 2016" (PDF). The Pharmacy Guild of Australia. 18 May 2016.{{cite web}}: CS1 maint: url-status (link)
^ "Trends & issues in crime and criminal justice No. 509, March 2016" (PDF). Australian Institute of Criminology. 7 March 2016. Retrieved 11 July 2024.{{cite web}}: CS1 maint: url-status (link)
^ "Project STOP mandatory for pharmacists in NSW from next month". Pulse.IT. 24 February 2016. Retrieved 11 July 2024.{{cite web}}: CS1 maint: url-status (link)
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
^ "Background on Update to NAPRA NHP Policy". napra.ca. 10 June 2024. Retrieved 11 July 2024.{{cite web}}: CS1 maint: url-status (link)
^ ^a ^b ^c Brunton LL, Lazo JS, Parker K, eds. (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill Medical Publishing Division. ISBN 0-07-142280-3.
^ Al-Ahmad M, Hassab M, Al Ansari A (21 December 2020). "Allergic and Non-allergic Rhinitis". Textbook of Clinical Otolaryngology. Cham: Springer International Publishing. pp. 241–252. doi:10.1007/978-3-030-54088-3_22. ISBN 978-3-030-54087-6. S2CID 234142758. Oral decongestants such as pseudoephedrine combined with an antihistamine and/or INC sprays are used in patients with nasal congestion.
^ Hodges K, Hancock S, Currell K, Hamilton B, Jeukendrup AE (February 2006). "Pseudoephedrine enhances performance in 1500-m runners". Medicine and Science in Sports and Exercise. 38 (2): 329–333. doi:10.1249/01.mss.0000183201.79330.9c. PMID 16531903.
^ Trinh KV, Kim J, Ritsma A (November 2015). "Effect of pseudoephedrine in sport: a systematic review". BMJ Open Sport & Exercise Medicine. 1 (1): e000066. doi:10.1136/bmjsem-2015-000066. PMC 5117033. PMID 27900142.
^ Ladenburg A, Oelschlägel C (1889). "Ueber das "Pseudo-Ephedrin"" [On pseudo-ephedrine]. Berichte der Deutschen Chemischen Gesellschaft (in German). 22 (2): 1823–1827. doi:10.1002/cber.18890220225. Archived from the original on 8 March 2021. Retrieved 19 May 2019.

[1] "Project STOP A Pharmacy Guild Initiative, May 2016" (PDF). The Pharmacy Guild of Australia. 18 May 2016.{{cite web}}: CS1 maint: url-status (link)

[2] "Trends & issues in crime and criminal justice No. 509, March 2016" (PDF). Australian Institute of Criminology. 7 March 2016. Retrieved 11 July 2024.{{cite web}}: CS1 maint: url-status (link)

[3] "Project STOP mandatory for pharmacists in NSW from next month". Pulse.IT. 24 February 2016. Retrieved 11 July 2024.{{cite web}}: CS1 maint: url-status (link)

[4] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.

[5] "Background on Update to NAPRA NHP Policy". napra.ca. 10 June 2024. Retrieved 11 July 2024.{{cite web}}: CS1 maint: url-status (link)

[goodman-gilman-6] Brunton LL, Lazo JS, Parker K, eds. (2006). Goodman & Gilman's The Pharmacological Basis of Therapeutics (11th ed.). New York: McGraw-Hill Medical Publishing Division. ISBN 0-07-142280-3.

[Al-Ahmad_Hassab_Al_Ansari_2020_pp._241–252-7] Al-Ahmad M, Hassab M, Al Ansari A (21 December 2020). "Allergic and Non-allergic Rhinitis". Textbook of Clinical Otolaryngology. Cham: Springer International Publishing. pp. 241–252. doi:10.1007/978-3-030-54088-3_22. ISBN 978-3-030-54087-6. S2CID 234142758. Oral decongestants such as pseudoephedrine combined with an antihistamine and/or INC sprays are used in patients with nasal congestion.

[8] Hodges K, Hancock S, Currell K, Hamilton B, Jeukendrup AE (February 2006). "Pseudoephedrine enhances performance in 1500-m runners". Medicine and Science in Sports and Exercise. 38 (2): 329–333. doi:10.1249/01.mss.0000183201.79330.9c. PMID 16531903.

[9] Trinh KV, Kim J, Ritsma A (November 2015). "Effect of pseudoephedrine in sport: a systematic review". BMJ Open Sport & Exercise Medicine. 1 (1): e000066. doi:10.1136/bmjsem-2015-000066. PMC 5117033. PMID 27900142.

[10] Ladenburg A, Oelschlägel C (1889). "Ueber das "Pseudo-Ephedrin"" [On pseudo-ephedrine]. Berichte der Deutschen Chemischen Gesellschaft (in German). 22 (2): 1823–1827. doi:10.1002/cber.18890220225. Archived from the original on 8 March 2021. Retrieved 19 May 2019.

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Pseudoephedrine

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