Oxilofrine

Oxilofrine

Systematic (IUPAC) name
(1S*,2R*)-(±)-4-(1-Hydroxy-2-methylamino-propyl)phenol
Clinical data
Legal status	Uncontrolled
Identifiers
CAS Number	365-26-4 N
ATC code	none
PubChem	CID: 9701
ChemSpider	9320 Y
UNII	F49638UBDR Y
KEGG	D08314 Y
ChEMBL	CHEMBL30400 Y
Chemical data
Formula	C10H15NO2
Molecular mass	181.23 g/mol
InChI InChI=1S/C10H15NO2/c1-7(11-2)10(13)8-3-5-9(12)6-4-8/h3-7,10-13H,1-2H3 Y Key:OXFGTKPPFSCSMA-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Oxilofrine (also known as methylsynephrine, hydroxyephrine, oxyephrine, and 4-HMP) is a stimulant drug and is an amphetamine chemically related to ephedrine and to synephrine.

Oxilofrine is currently a WADA prohibited substance when used in competition. It is an ingredient found in some dietary supplements.

Publicized cases

• In 2009, Brazilian/American cyclist Flávia Oliveira was suspended for 2 years after taking a supplement known as "HyperDrive 3.0+" which contained methylsynephrine, a chemical equivalent of Oxilofrine, among other substances. Her sentence was eventually reduced to 18 months after an appeal as there was enough evidence that she had unknowingly consumed said substance as the old label did not list methylsynephrine.
• On July 14th, 2013, Jamaican runners Asafa Powell and Sherone Simpson tested positive for Oxilofrine prior to the 2013 World Athletics Championships. Powell, however, maintained that he did not take any banned supplements knowingly or willfully. Powell voluntarily withdrew as a result of the test. On 10 April 2014, both athletes received an 18-month suspension from competing, which was set to expire in December that year. However, after appealing to the Court of Arbitration for Sport (CAS), both athletes' suspensions were lifted on 14 July 2014.