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Pseudoephedrine information


Pseudoephedrine
Clinical data
Pronunciation/ˌsd.ɪˈfɛdrɪn, -ˈɛfɪdrn/
Trade namesAfrinol, Sudafed, Sinutab, others
AHFS/Drugs.comMonograph
MedlinePlusa682619
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)
  • BR: Class D1 (Drug precursors)[1]
  • CA: OTC; NDS Schedule II for single-drug products, NDS Schedule III (OTC) when part of a combination product
  • UK: P (Pharmacy medicines)
  • US: OTC
Pharmacokinetic data
Bioavailability~100%[2]
Metabolism10–30% liver
Elimination half-life4.3–8 hours[2]
Excretion43–96% kidney[2]
Identifiers
IUPAC name
  • (S,S)-2-methylamino-1-phenylpropan-1-ol
CAS Number
  • 90-82-4 checkY
PubChem CID
  • 7028
DrugBank
  • DB00852 checkY
ChemSpider
  • 6761 checkY
UNII
  • 7CUC9DDI9F
KEGG
  • D08449 checkY
ChEBI
  • CHEBI:51209 checkY
ChEMBL
  • ChEMBL1590 checkY
CompTox Dashboard (EPA)
  • DTXSID0023537 Edit this at Wikidata
ECHA InfoCard100.001.835 Edit this at Wikidata
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 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 checkY
  • Key:KWGRBVOPPLSCSI-WCBMZHEXSA-N checkY
  (verify)

Pseudoephedrine (PSE) is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant,[3] as a stimulant, or as a wakefulness-promoting agent[4] in higher doses.[5]

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.[6] 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).

  1. ^ 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.
  2. ^ 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.
  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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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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Phenylephrine

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medical use in 1938. It is available as a generic medication. Unlike pseudoephedrine, abuse of phenylephrine is very uncommon. Its effectiveness as a nasal...

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Ephedrine

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pressure, heart rate and contractility. Like pseudoephedrine it is a bronchodilator, with pseudoephedrine having considerably less effect. Ephedrine may...

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Phenylephrine (5 mg/pill) (nasal decongestant) NyQuil D contains pseudoephedrine, a decongestant that in some regions (such as the United States) is...

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Priapism

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pseudoephedrine is a first-line treatment for priapism. Erection is largely a parasympathetic response, so the sympathetic action of pseudoephedrine may...

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Loratadine

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available in drug combinations such as loratadine/pseudoephedrine, in which it is combined with pseudoephedrine, a nasal decongestant. It is taken orally. Common...

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Triprolidine

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was patented in 1948 and came into medical use in 1953. Benzatropine Pseudoephedrine UK-9040 Goldsmith P, Dowd PM (January 1993). "The new H1 antihistamines...

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Cold medicine

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congestion in sinus infections. Examples are ephedrine, phenylephrine, pseudoephedrine, and oxymetazoline. Fever or pain medication. Examples are paracetamol...

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Actifed

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GlaxoSmithKline), later Haleon. The original formula for Actifed contained pseudoephedrine hydrochloride 60 mg as the nasal decongestant and triprolidine hydrochloride...

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Decongestant

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respiratory tract. The active ingredient in most decongestants is either pseudoephedrine or phenylephrine (the latter of which has disputed effectiveness)....

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Chiral auxiliary

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Both enantiomers of pseudoephedrine are commercially available. Racemic pseudoephedrine has many medical uses. Because pseudoephedrine can be used to illegally...

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Standard for the Uniform Scheduling of Medicines and Poisons

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advertised to the public. Examples: Orlistat (trade name Xenical) Pseudoephedrine (marketed in Cold and Flu preparations) Salbutamol (Ventolin/Asmol)...

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Benadryl

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sneezing. This version contains acrivastine and pseudoephedrine as its active ingredients. Pseudoephedrine is a decongestant used to relieve a nasal congestion...

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Stimulant

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longer, it is said to have ergogenic effects. Drugs such as ephedrine, pseudoephedrine, amphetamine and methylphenidate have well documented ergogenic effects...

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Zhenli Ye Gon

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Chinese-Mexican businessman currently under suspicion of trafficking pseudoephedrine or ephedrine precursor chemicals into Mexico from Asia. He is the owner...

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Guaifenesin

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as paracetamol/acetaminophen, and decongestants such as ephedrine, pseudoephedrine, or phenylephrine. In 2014, sales of guaifenesin were estimated to...

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Sympathomimetic drug

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Known reports of such hypersensitivity reactions include the use of pseudoephedrine, phenylpropanolamine, methamphetamine and other drugs at prescribed...

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Methamphetamine in the United States

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methamphetamine. Methamphetamine can be produced in home laboratories using pseudoephedrine or ephedrine, which, at the time, were the active ingredients in over-the-counter...

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Methcathinone

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substituent. Its carbon skeleton is identical to pseudoephedrine and methamphetamine. It differs from pseudoephedrine in that the hydroxide beta to the aromatic...

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Hydrochloride

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(1999). "Asymmetric Synthesis of α-Amino Acids by the Alkylation of Pseudoephedrine Glycinamide: L-Allylglycine and N-BOC-l-Allylglycine". Organic Syntheses...

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Vasoconstriction

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administration vary. They may be both systemic and topical. For example, pseudoephedrine is taken orally and phenylephrine is topically applied to the nasal...

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