New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites

Publikation: Beitrag in FachzeitschriftForschungsartikelBeigetragenBegutachtung


  • Steffen Loke - , Charité – Universitätsmedizin Berlin (Erstautor:in)
  • Lingyu Liu - , Charité – Universitätsmedizin Berlin (Autor:in)
  • Maxi Wenzel - , Charité – Universitätsmedizin Berlin (Autor:in)
  • Heike Scheffler - , Charité – Universitätsmedizin Berlin (Autor:in)
  • Michele Iannone - , Laboratorio Antidoping FMSI (Autor:in)
  • Xavier de la Torre - , Laboratorio Antidoping FMSI (Autor:in)
  • Nils Schlörer - , Institute for Organic Chemistry (Autor:in)
  • Francesco Botrè - , Laboratorio Antidoping FMSI (Autor:in)
  • Annekathrin Martina Keiler - , Umweltmonitoring und Endokrinologie (FoG), Institut für Dopinganalytik und Sportbiochemie Dresden (Autor:in)
  • Matthias Bureik - , Tianjin University (Autor:in)
  • Maria Kristina Parr - , Charité – Universitätsmedizin Berlin (Letztautor:in)


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.


PublikationsstatusVeröffentlicht - 3 März 2021

Externe IDs

PubMedCentral PMC7961831
Scopus 85103920153
ORCID /0000-0002-2157-4711/work/142251653



  • Anabolic Agents/chemistry, Gas Chromatography-Mass Spectrometry, Healthy Volunteers, Humans, Methandrostenolone/chemistry, Methyltestosterone/chemistry, Middle Aged, Reference Standards, Tandem Mass Spectrometry