Oxilofrine

• 4- hydroxyephedrine
• (1S *, 2R * ) - ( ±) -4 - [1- hydroxy-2- (methylamino ) propyl ] phenol (IUPAC)
• Erythro -p -hydroxy- α -[1 - (methylamino ) ethyl] benzyl alcohol

• 365-26-4
• 942-51-8 Oxilofrinhydrochlorid

C01CB04

Sympathomimetic

153 ° C

150 mg · kg -1 ( LDLO, rabbits, i.v.)

Template: Infobox chemical / molecular formula search available

Oxilofrine (trade name: Carnigen ) is a drug from the group of sympathomimetics used for the treatment of low blood pressure ( orthostatic hypotension) is applied.

Chemical structure and stereoisomerism

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

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

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

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

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

Are not included in oxilofrine.

Mechanism of Action

About the agonist effects of sympathomimetic oxilofrine to adrenoceptors are found in the literature, various information:

• α -agonist
• α - and β -agonist
• β1 - β2 -agonist and

Doping

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