Oxilofrine

Oxilofrine

Clinical data
ATC code	none
Legal status
Legal status	Uncontrolled
Identifiers
IUPAC name (1S*,2R*)-(±)-4-(1-Hydroxy-2-methylamino-propyl)phenol
CAS Number	365-26-4
PubChem (CID)	9701
ChemSpider	9320
UNII	F49638UBDR
KEGG	D08314
ChEMBL	CHEMBL30400
ECHA InfoCard	100.006.067
Chemical and physical data
Formula	C10H15NO2
Molar 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 Key:OXFGTKPPFSCSMA-UHFFFAOYSA-N
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Oxilofrine (also known as methylsynephrine, hydroxyephrine, oxyephrine, and 4-HMP) is a stimulant drug^[1] and is an amphetamine chemically related to ephedrine and to synephrine.

Oxilofrine is currently a WADA prohibited substance when used in competition.^[2] 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. ^[3] 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.^[4]
• On July 14, 2013, Jamaican runners Asafa Powell and Sherone Simpson tested positive for oxilofrine prior to the 2013 World Athletics Championships. ^[5] Powell, however, maintained that he did not take any banned supplements knowingly or willfully.^[6] 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.^[7] However, after appealing to the Court of Arbitration for Sport (CAS), both athletes' suspensions were lifted on 14 July 2014.^[8]
• On July 16, 2015, Boston Red Sox pitching prospect Michael Kopech was suspended without pay for 50 games after testing positive for oxilofrine, which is a banned substance under the Minor League Drug Prevention and Treatment Program. Kopech denied knowingly taking the substance.^[9]

References

1. Fourcroy, Jean L. (2008). Pharmacology, doping and sports: a scientific guide for athletes, coaches, physicians, scientists and administrators. Taylor & Francis. ISBN 978-0-415-42845-3.
2. http://list.wada-ama.org/prohibited-in-competition/prohibited-substances/
3. Charles Pelkey (2010-04-13). "Oliveira suspended for two years". Velonews.
4. Charles Pelkey (2011-02-24). "Court of Arbitration for Sport reduces Flavia Oliveira suspension". Velonews.
5. Reuters. "Jamaicans Powell, Simpson test positive - SuperSport - Athletics". SuperSport. Retrieved 2013-07-15.
6. "Jamaican Sprinter Asafa Powell slapped 18-month ban for doping". IANS. news.biharprabha.com. Retrieved 10 April 2014.
7. "Asafa Powell banned for 18 months for doping". BBC Sport. 10 April 2014. Archived from the original on 9 May 2014.
8. Drayton, John (14 July 2014). "Asafa Powell and Sherone Simpson given green light to return to action after sprinters have doping bans reduced to six months". Mail Online. Retrieved 14 July 2014.
9. Danny Wild (16 July 2015). "Red Sox No. 10 prospect Kopech suspended". MiLB.com. Retrieved 8 March 2016.