6α-Methylandrostenedione: gas chromatographic mass spectrometric detection in doping control
Article first published online: 8 JAN 2008
Copyright © 2008 John Wiley & Sons, Ltd.
Rapid Communications in Mass Spectrometry
Volume 22, Issue 3, pages 321–329, 15 February 2008
How to Cite
Parr, M. K., Kazlauskas, R., Schlörer, N., Opfermann, G., Piper, T., Schulze, G. and Schänzer, W. (2008), 6α-Methylandrostenedione: gas chromatographic mass spectrometric detection in doping control. Rapid Commun. Mass Spectrom., 22: 321–329. doi: 10.1002/rcm.3367
- Issue published online: 10 JAN 2008
- Article first published online: 8 JAN 2008
- Manuscript Revised: 19 NOV 2007
- Manuscript Accepted: 19 NOV 2007
- Manuscript Received: 18 SEP 2007
- Manfred Donike Institute for Doping Analyses e.V., Cologne
In recent years products containing 6α-methylandrost-4-ene-3,17-dione have appeared on the sport supplement market. Scientific studies have proven aromatase inhibition and anabolic and mild androgenic properties; however, no preparation has been approved for medical use up to now. In sports 6α-methylandrost-4-ene-3,17-dione has to be classified as a prohibited substance according to the regulations of the World Anti-Doping Agency (WADA). For the detection of its misuse the metabolism was studied following the administration of two preparations obtained from the Internet (Formadrol and Methyl-1-Pro). Several metabolites as well as the parent compounds were synthesized and the structures of 3α-hydroxy-6α-methyl-5β-androstan-17-one, 6α-methylandrost-4-ene-3,17-dione, and 5β-dihydromedroxyprogesterone were confirmed by nuclear magnetic resonance (NMR) spectroscopy. The main metabolite, 3α-hydroxy-6α-methyl-5β-androstan-17-one, was found to be excreted as glucuronide and was still detectable in µg/mL amounts until urine collection was terminated (after 25 h). Additionally, samples from routine human sports doping control had already tested positive for the presence of metabolites of 6α-methylandrost-4-ene-3,17-dione. Screening analysis can be easily performed by the existing screening procedure for anabolic steroids using 3α-hydroxy-6α-methyl-5β-androstan-17-one as target substance (limit of detection <10 ng/mL). Its discrimination from the closely eluting drostanolone metabolite, 3α-hydroxy-2α-methyl-5α-androstan-17-one, is possible as the mono-TMS derivative. Copyright © 2008 John Wiley & Sons, Ltd.