Synthesis and identification of hydroxylated metabolites of the anti-estrogenic agent cyclofenil.
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.
Gärtner
Peter
P
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Vienna, Austria.
Hofbauer
Karin
K
Reichel
Christian
C
Geisendorfer
Thomas
T
Gmeiner
Günter
G
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*
D020847:Estrogen Receptor Modulators; D013287:Illicit Drugs; D003506:Cyclofenil