Oxilofrine

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
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.067
Chemical and physical data
FormulaC10H15NO2
Molar mass181.235 g·mol−1
 NY (what is this?)  (verify)

Oxilofrine is currently a World Anti-Doping Agency (WADA) prohibited substance when used in competition.[2] It has been found as an adulterant in some dietary supplements.[3][4] Even after receiving warning letters from the FDA,[5] some sports and weight loss supplement companies continue to use oxilofrine as an undeclared ingredient in their products despite it being prohibited.[6]

Doping cases

Several doping cases involving athletes have been publicized, including:

  • 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.[7] 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.[8]
  • On July 14, 2013, Jamaican runners Asafa Powell and Sherone Simpson tested positive for oxilofrine prior to the 2013 World Athletics Championships.[9] Powell, however, maintained that he did not take any banned supplements knowingly or willfully.[10] 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.[11] However, after appealing to the Court of Arbitration for Sport (CAS), both athletes' suspensions were lifted on 14 July 2014.[12]
  • On July 16, 2015, 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.[13]
  • In October 2018, the WBO stripped boxer Billy Joe Saunders of its middleweight world title after he tested positive for oxilofrine, as a result of a drug test administered by the Voluntary Anti-Doping Association. In his defense, Saunders held that while the substance was proscribed by VADA it was not banned "out of competition" by UK Anti-Doping, or the British Boxing Board of Control, but this appeal was rejected.[14]

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. "Archived copy". Archived from the original on 2013-07-02. Retrieved 2013-07-15.CS1 maint: archived copy as title (link)
  3. Cohen, Pieter A.; Avula, Bharathi; Venhuis, Bastiaan; Travis, John C.; Wang, Yan-Hong; Khan, Ikhlas A. (2017). "Pharmaceutical doses of the banned stimulant oxilofrine found in dietary supplements sold in the USA". Drug Testing and Analysis. 9 (1): 135–142. doi:10.1002/dta.1976. PMID 27062112.
  4. Zovko Končić, Marijana (2018). "Getting More Than You Paid For: Unauthorized 'Natural' Substances in Herbal Food Supplements on EU Market". Planta Medica. 84 (6/07): 394–406. doi:10.1055/s-0044-100042. PMID 29341031.
  5. Nutrition, Center for Food Safety and Applied. "Products & Ingredients - Methylsynephrine in Dietary Supplements". www.fda.gov.
  6. Cohen, Pieter A.; Wen, Anita; Gerona, Roy (1 December 2018). "Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration". JAMA Internal Medicine. 178 (12): 1721. doi:10.1001/jamainternmed.2018.4846.
  7. Charles Pelkey (2010-04-13). "Oliveira suspended for two years". Velonews. Archived from the original on 2015-10-06.
  8. Charles Pelkey (2011-02-24). "Court of Arbitration for Sport reduces Flavia Oliveira suspension". Velonews. Archived from the original on 2015-12-23.
  9. Reuters. "Jamaicans Powell, Simpson test positive - SuperSport - Athletics". SuperSport. Retrieved 2013-07-15.
  10. "Jamaican Sprinter Asafa Powell slapped 18-month ban for doping". IANS. news.biharprabha.com. Archived from the original on 14 April 2014. Retrieved 10 April 2014.
  11. "Asafa Powell banned for 18 months for doping". BBC Sport. 10 April 2014. Archived from the original on 9 May 2014.
  12. 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. Archived from the original on 17 July 2014. Retrieved 14 July 2014.
  13. Danny Wild (16 July 2015). "Red Sox No. 10 prospect Kopech suspended". MiLB.com. Archived from the original on 9 March 2016. Retrieved 8 March 2016.
  14. Elliot Worsell (12 October 2018). "The ins and outs of Billy Joe Saunders, oxilofrine and VADA". http://www.boxingnewsonline.net/.
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