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Another designer steroid: discovery, synthesis, and detection of ‘madol’ in urine
Author(s) -
Sekera Michael H.,
Ahrens Brian D.,
Chang YuChen,
Starcevic Borislav,
Georgakopoulos Costas,
Catlin Don H.
Publication year - 2005
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.1858
Subject(s) - chemistry , metabolite , urine , chromatography , steroid , context (archaeology) , mass spectrometry , anabolism , gas chromatography–mass spectrometry , biochemistry , hormone , paleontology , biology
Madol (17 α ‐methyl‐5 α ‐androst‐2‐en‐17 β ‐ol) was identified in an oily product received by our laboratory in the context of our investigations of designer steroids. The product allegedly contained an anabolic steroid not screened for in routine sport doping control urine tests. Madol was synthesized by Grignard methylation of 5 α ‐androst‐2‐en‐17‐one and characterized by mass spectrometry and NMR spectroscopy. We developed a method for rapid screening of urine samples by gas chromatography/mass spectrometry (GC/MS) of trimethylsilylated madol (monitoring m/z 143, 270, and 345). A baboon administration study showed that madol and a metabolite are excreted in urine. In vitro incubation with human liver microsomes yielded the same metabolite. Madol is only the third steroid never commercially marketed to be found in the context of performance‐enhancing drugs in sports. Copyright © 2005 John Wiley & Sons, Ltd.