New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites
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Contributors
Abstract
Metandienone and methyltestosterone are orally active anabolic-androgenic steroids with a 17α-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 17ξ-hydroxymethyl-17ξ-methyl-18-nor-5ξ-androst-13-en-3ξ-ol structure in the chlorinated metandienone analog dehydrochloromethyltestosterone ("oral turinabol"), in this study we investigated the formation of similar metabolites of metandienone and 17α-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. 17α-hydroxymethyl-17β-methyl-18-nor-5β-androst-13-en-3α-ol and its 5α-analog, were identified following an administration of methyltestosterone. In post-administration urines of metandienone, only the 5β-metabolite was detected. Additionally, 3α,5β-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 17α-methyl steroids with respect to the order of reductions in the A-ring, the participation of different enzymes, and alterations to the D-ring.
Details
Original language | English |
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Article number | 1354 |
Journal | Molecules |
Volume | 26 |
Issue number | 5 |
Publication status | Published - 3 Mar 2021 |
Peer-reviewed | Yes |
External IDs
PubMedCentral | PMC7961831 |
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Scopus | 85103920153 |
ORCID | /0000-0002-2157-4711/work/142251653 |
Keywords
Keywords
- Anabolic Agents/chemistry, Gas Chromatography-Mass Spectrometry, Healthy Volunteers, Humans, Methandrostenolone/chemistry, Methyltestosterone/chemistry, Middle Aged, Reference Standards, Tandem Mass Spectrometry