title: Another designer steroid: discovery, synthesis, and detection of 'madol' in urine.
abstract: Madol (17alpha-methyl-5alpha-androst-2-en-17beta-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 5alpha-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.
authors.affiliation: UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Ave., Los Angeles, CA 90025, USA.
authors.forename: Michael H
authors.initials: MH
authors.lastname: Sekera
authors.forename: Brian D
authors.initials: BD
authors.lastname: Ahrens
authors.forename: Yu-Chen
authors.initials: YC
authors.lastname: Chang
authors.forename: Borislav
authors.initials: B
authors.lastname: Starcevic
authors.forename: Costas
authors.initials: C
authors.lastname: Georgakopoulos
authors.forename: Don H
authors.initials: DH
authors.lastname: Catlin
mesh_terms: D045930:Anabolic Agents / Q000737:chemistry / Q000652:urine; D000737:Androstenols / Q000138:chemical synthesis / Q000737:chemistry / Q000652:urine*; D000818:Animals; D015198:Designer Drugs / Q000032:analysis*; D004300:Doping in Sports / Q000379:methods* / Q000517:prevention & control*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D006801:Humans; D008657:Metabolic Clearance Rate; D010215:Papio; D015813:Substance Abuse Detection / Q000379:methods*; D016482:Urinalysis / Q000379:methods*
chemical_list: D045930:Anabolic Agents; D000737:Androstenols; D015198:Designer Drugs; C500374:17-methylandrost-2-en-17-ol