Oxilofrine

Structural formula
	(1 R , 2 S ) form (left) and (1 S , 2 R ) form (right), 1: 1 mixture of stereoisomers
General
Non-proprietary name	Oxilofrine
other names	4-hydroxyephedrine; (1 S * , 2 R * ) - (±) -4- [1-Hydroxy-2- (methylamino) propyl] phenol ( IUPAC ) ; erythro- p-hydroxy-α- [1- (methylamino) ethyl] benzyl alcohol;
Molecular formula	C 10 H 15 NO 2
External identifiers / databases
EC number	206-672-3
ECHA InfoCard	100.006.067
PubChem	9701
Wikidata	Q1689157
Drug information
ATC code	C01 CB04
Drug class	Sympathomimetic
properties
Molar mass	181.23 g · mol -1
Physical state	firmly
Melting point	153 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	150 mg kg −1 ( LD Lo , rabbit , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxilofrin (trade name: Carnigen ) is a drug from the group of sympathomimetics which is used to treat low blood pressure ( orthostatic hypotension ).

Chemical structure and stereoisomerism

Oxilofrin differs from ephedrine only by an additional hydroxy group on the benzene ring , hence the name hydroxyephedrine or more precisely 4-hydroxyephedrine .

Oxilofrin is a 1: 1 mixture ( racemate ) of the following two stereoisomers:

(1 S , 2 R ) -4- [1-Hydroxy-2- (methylamino) propyl] phenol and
(1 R , 2 S ) -4- [1-Hydroxy-2- (methylamino) propyl] phenol

Since 4- [1-hydroxy-2- (methylamino) propyl] phenol contains two stereocenters, there are four stereoisomers of which

(1 S , 2 S ) -4- [1-Hydroxy-2- (methylamino) propyl] phenol and
(1 R , 2 R ) -4- [1-Hydroxy-2- (methylamino) propyl] phenol

are not contained in Oxilofrin.

Mechanism of action

Various information can be found in the literature about the agonistic effects of the sympathomimetic oxilofrin on adrenoceptors :

α-agonistic
α- and β-agonistic
β ₁ - and β ₂ -agonistic

doping

Oxilofrin is listed on the World Anti-Doping Agency (WADA) list as a stimulant that is banned during athletic competitions.

Individual evidence

↑ ^a ^b Entry on Oxilofrin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 1, 2018.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ AGES-PharmMed, stand; October 2009.
↑ HJ Roth u. H. Fenner: Drugs . Thieme, Stuttgart a. New York 1988, p. 409.
↑ Andreas Russ: Medicines pocket . 13th edition Börm Bruckmeier, Grünwald 2007, p. 41.
^ Roche Lexicon Medicine . 5th edition Urban & Fischer, Munich a. Jena 2003.
↑ The World Anti-Doping Code: The 2009 Prohibited List, International Standard , p. 7 ( Memento of July 19, 2014 in the Internet Archive ) (PDF; 177 kB).

[ChemIDplus-1] Entry on Oxilofrin in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 1, 2018.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] AGES-PharmMed, stand; October 2009.

[4] HJ Roth u. H. Fenner: Drugs . Thieme, Stuttgart a. New York 1988, p. 409.

[5] Andreas Russ: Medicines pocket . 13th edition Börm Bruckmeier, Grünwald 2007, p. 41.

[6] Roche Lexicon Medicine . 5th edition Urban & Fischer, Munich a. Jena 2003.

[7] The World Anti-Doping Code: The 2009 Prohibited List, International Standard , p. 7 ( Memento of July 19, 2014 in the Internet Archive ) (PDF; 177 kB).