title: Synthesis and identification of hydroxylated metabolites of the anti-estrogenic agent cyclofenil.
abstract: The detection of metabolites of the anti-estrogenic substance cyclofenil, listed on the World Anti-Doping Agency (WADA) Prohibited List since 2004 is described. Target substances are hydroxylated metabolites, bearing an aliphatic hydroxyl group either in the 2-, 3- or 4-position of the aliphatic ring, in addition to the phenolic functions on the aromatic rings. Structural identification used NMR as well as high-resolution mass spectrometry after nano-electrospray ionisation (ESI). Unambiguous detection of all three synthesised cyclofenil metabolites M1-M3 was done using gas chromatography for separation and electron ionisation mass spectrometry for detection of the per-silylated compounds in comparison with a reference urine deriving from an excretion study within the WADA 2007 Educational Programme.
authors.affiliation: Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria.
authors.forename: Peter
authors.initials: P
authors.lastname: Gärtner
authors.forename: Karin
authors.initials: K
authors.lastname: Hofbauer
authors.forename: Christian
authors.initials: C
authors.lastname: Reichel
authors.forename: Thomas
authors.initials: T
authors.lastname: Geisendorfer
authors.forename: Günter
authors.initials: G
authors.lastname: Gmeiner
mesh_terms: D002849:Chromatography, Gas; D003506:Cyclofenil / Q000031:analogs & derivatives / Q000737:chemistry / Q000652:urine; D004300:Doping in Sports; D020847:Estrogen Receptor Modulators / Q000737:chemistry / Q000652:urine; D006801:Humans; D006900:Hydroxylation; D013287:Illicit Drugs / Q000138:chemical synthesis* / Q000652:urine; D036103:Nanotechnology; D021241:Spectrometry, Mass, Electrospray Ionization; D015813:Substance Abuse Detection / Q000379:methods*
chemical_list: D020847:Estrogen Receptor Modulators; D013287:Illicit Drugs; D003506:Cyclofenil