Another designer steroid: discovery, synthesis, and detection of 'madol' in urine
Madol (17α‐methyl‐5α‐androst‐2‐en‐17β‐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...
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| Veröffentlicht in: | Rapid communications in mass spectrometry 2005-01, Vol.19 (6), p.781-784 |
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| container_title | Rapid communications in mass spectrometry |
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| creator | Sekera, Michael H. Ahrens, Brian D. Chang, Yu-Chen Starcevic, Borislav Georgakopoulos, Costas Catlin, Don H. |
| description | Madol (17α‐methyl‐5α‐androst‐2‐en‐17β‐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 5α‐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. |
| doi_str_mv | 10.1002/rcm.1858 |
| format | Article |
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Mass Spectrom</addtitle><description>Madol (17α‐methyl‐5α‐androst‐2‐en‐17β‐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 5α‐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. 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Mass Spectrom</addtitle><date>2005-01-01</date><risdate>2005</risdate><volume>19</volume><issue>6</issue><spage>781</spage><epage>784</epage><pages>781-784</pages><issn>0951-4198</issn><eissn>1097-0231</eissn><abstract>Madol (17α‐methyl‐5α‐androst‐2‐en‐17β‐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 5α‐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. 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| source | MEDLINE; Wiley Online Library All Journals |
| subjects | Anabolic Agents - chemistry Anabolic Agents - urine Androstenols - chemical synthesis Androstenols - chemistry Androstenols - urine Animals Designer Drugs - analysis Doping in Sports - methods Doping in Sports - prevention & control Gas Chromatography-Mass Spectrometry - methods Humans Metabolic Clearance Rate Papio Substance Abuse Detection - methods Urinalysis - methods |
| title | Another designer steroid: discovery, synthesis, and detection of 'madol' in urine |
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