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.
Highlights
Licensee MDPI, Basel, Switzerland.Metandienone (17β-hydroxy-17α-methyl-androsta-1,4-dien-3-one, MD, 12; list of steroids available in supplement S1) and methyltestosterone (17β-hydroxy-17α-methylandrost-4-en3-one, MT, 18) are anabolic-androgenic steroids
The method was adapted from Kratena et al [33] but started with regu3ξ-ols were synthesized using 3-hydroxyandostan-17-ones as starting material by modi larly C13β-CH3 configured androstanes in contrast to the ent-configurated (C13α-CH3 )
The method was adapted from Kratena et al [33] but started with regu androstanes used by Kratena et al As the first step of synthesis, attachment of an addilarly C13β-CH
Summary
Stances are frequently by as gasaglycons chromatography-mass spectrometry after hydrolother steroidsbond with of a similar structure, such as dehydrochloromethyltestosterone, ysis For of the glycosidic glucuronides as aglycons there is a metabolite described with a fully reduced A-ring and a rearranged D-ring [30], which was synthesized in 2018 [31,32]. This metabolite led to an extended detection time.
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