Journal
MOLECULES
Volume 26, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/molecules26051354
Keywords
17α -methyl steroids; long-term metabolites; gas chromatography-mass spectrometry; 17-hydroxymethyl-17-methyl-18-nor; D-ring alteration; doping control; metabolism
Funding
- Freie Universitat Berlin
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This study identified new metabolites of metandienone and 17α-methyltestosterone, providing new insights into the metabolism of these synthetic steroids.
Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17 alpha-methyl structure that are prohibited in sports but are frequently detected in anti-doping analysis. Following the previously reported detection of long-term metabolites with a 17 xi-hydroxymethyl-17 xi-methyl-18-nor-5 xi-androst-13-en-3 xi-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone (oral turinabol), in this study we investigated the formation of similar metabolites of metandienone and 17 alpha-methyltestosterone with a rearranged D-ring and a fully reduced A-ring. Using a semi-targeted approach including the synthesis of reference compounds, two diastereomeric substances, viz. 17 alpha-hydroxymethyl-17 beta-methyl-18-nor-5 beta-androst-13-en-3 alpha-ol and its 5 alpha-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5 beta-metabolite was detected. Additionally, 3 alpha,5 beta-tetrahydro-epi-methyltestosterone was identified in the urines of both administrations besides the classical metabolites included in the screening procedures. Besides their applicability for anti-doping analysis, the results provide new insights into the metabolism of 17 alpha-methyl steroids with respect to the order of reductions in the A-ring, the participation of different enzymes, and alterations to the D-ring.
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