Pseudoephedrine

Structural formula
General
Non-proprietary name	Pseudoephedrine
other names	(+) - (1 S , 2 S ) -2-methylamino-1-phenyl-propan-1-ol
Molecular formula	C 10 H 15 NO
Brief description	colorless crystals
External identifiers / databases
ECHA InfoCard	100.001.835
PubChem	7028
DrugBank	DB00852
Wikidata	Q263958
Drug information
ATC code	R01 BA02
Drug class	Sympathomimetic
Mechanism of action	indirect sympathomimetic
properties
Molar mass	165.232 g mol −1 ; 201.7 g mol −1 (hydrochloride); 428.5 g mol −1 (sulfate);
Melting point	119 ° C; 182.5-183.5 ° C ( hydrochloride ); 174–179 ° C (sulfate);
pK s value	10.252
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-315-319-332-335
	P: 261-280-305 + 351 + 338
Toxicological data	500 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pseudoephedrine is a phenylethylamine - alkaloid with stimulant and vasoconstrictor effect. It is the diastereomer of ephedrine and, like this, belongs to the indirect sympathomimetics and is often used as a cold remedy.

Occurrence and extraction

It can be obtained from some plant species of the genus Ephedra ( Ephedra L. ), and is also found in the Indian mallow ( Sida cordifolia ) and in the Asian spotted poppy ( Roemeria refracta ).

Mongolian Sea Crow ( Ephedra equisetina )
Indian mallow ( Sida cordifolia )
Asian spotted poppy ( Roemeria refracta )

pharmacology

Pseudoephedrine causes catecholamines to be released mainly in the periphery of the body and prevents their re- absorption into the presynapse . As a result, it has a vasoconstricting effect and allows the nasal mucosa to swell in the case of colds and allergies . However, it is inferior to a locally applied direct sympathomimetic ( agonist at alpha-1 adrenoceptors ) such as xylometazoline . The plasma half-life is approximately 9-16 hours.

Known side effects when taking it include palpitations , increased blood pressure , restlessness, insomnia and anxiety up to hallucinations .

doping

Since pseudoephedrine is often found in cold medicines, it was - previously on the IOC's doping list - deleted from this list in 2002. Since January 1, 2010, however, it has been on the WADA prohibited list again .

The best-known case of doping with pseudoephedrine concerned Romanian gymnast Andreea Răducan , who had to return her gold medal at the 2000 Olympic Games because she had taken a drug containing pseudoephedrine before a competition. In a doping control, taking pseudoephedrine, similar to ephedrine, leads to a positive test result.

Trade names

Monopreparations

Rinoral, formerly Otrinol (CH)

Combination preparations

Aerinaze (A), Aspirin complex (D, A, CH), Benical (CH), BoxaGrippal (D, A), Cirrus (PL), Clarinase (A), Disofrol (CH), DuoGrippal (D), Fluimucil Grippe ( CH), Olytabs (D), Panadol Antigrippine (CH), Pretuval (CH), ratioGrippal (D), Reactine duo (D), Rhinopront (D), RhinAdvil (F), SpaltGrippal (D), TylolHot (TR), Wick DayNait

Web links

drug telegram: Aspirin Complex with pseudoephedrine

Individual evidence

↑ ^a ^b ^c data sheet (+) - Pseudoephedrine from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).
↑ ^a ^b ^c Entry on pseudoephedrine in the ChemIDplus database of the United States National Library of Medicine (NLM)
^ ^A ^b Royal Pharmaceutical Society (ed.): Clarke's Analysis of Drugs and Poisons FOURTH EDITION . Pharmaceutical Press, London / Chicago 2011, ISBN 978-0-85369-711-4 .
↑ Federal Institute for Risk Assessment : Risk Assessment of Plants and Herbal Preparations, Ephedra spp. (Sea crow species). (PDF; 1.8 MB), Berlin 2012, ISBN 978-3-938163-76-4 , pp. 223-239.
↑ E. Beubler: Compendium of Pharmacology. Springer, Vienna 2006, p. 37.
↑ JC Selner et al: Assessment of nasal patency by rhinoscopic measurement of cross sectional nasal airway area: correlation with subjective nasal symptoms. In: Ann. Allergy. Volume 66, 1991, pp. 43-47. PMID 1702944 .
^ Entry on pseudoephedrine in the DrugBank of the University of Alberta .
^ WADA prohibited list for 2010 ( Memento of November 22, 2009 in the Internet Archive ) (PDF; 93 kB).
↑ Entry on pseudoephedrine in Pharmawiki , accessed on January 28, 2017.

[sigma-1] ta sheet (+) - Pseudoephedrine from Sigma-Aldrich , accessed on November 3, 2016 ( PDF ).

[ChemIDplus-2] Entry on pseudoephedrine in the ChemIDplus database of the United States National Library of Medicine (NLM)

[Clarke's_Analysis_of_Drugs_and_Poisons-3] A ^b Royal Pharmaceutical Society (ed.): Clarke's Analysis of Drugs and Poisons FOURTH EDITION . Pharmaceutical Press, London / Chicago 2011, ISBN 978-0-85369-711-4 .

[BfR-4] Federal Institute for Risk Assessment : Risk Assessment of Plants and Herbal Preparations, Ephedra spp. (Sea crow species). (PDF; 1.8 MB), Berlin 2012, ISBN 978-3-938163-76-4 , pp. 223-239.

[5] E. Beubler: Compendium of Pharmacology. Springer, Vienna 2006, p. 37.

[6] JC Selner et al: Assessment of nasal patency by rhinoscopic measurement of cross sectional nasal airway area: correlation with subjective nasal symptoms. In: Ann. Allergy. Volume 66, 1991, pp. 43-47. PMID 1702944 .

[7] Entry on pseudoephedrine in the DrugBank of the University of Alberta .

[8] WADA prohibited list for 2010 ( Memento of November 22, 2009 in the Internet Archive ) (PDF; 93 kB).

[9] Entry on pseudoephedrine in Pharmawiki , accessed on January 28, 2017.