Oxilofrine

From Wikipedia, the free encyclopedia

Jump to: navigation, search
Oxilofrine
Oxilofrin Structural Formulae V.1.svg
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 YesY
UNII F49638UBDR YesY
KEGG D08314 YesY
ChEMBL CHEMBL30400 YesY
Chemical data
Formula C10H15NO2
Molar mass 181.23 g/mol
 NYesY (what is this?)  (verify)

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[edit]

  • 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[edit]

  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.