Alternative long-term markers for the detection of methyltestosterone misuse

Alternative long-term markers for the detection of methyltestosterone misuse / C Gómez, O.J. Pozo, J. Marcos, J. Segura, R. Ventur. - (Steroids 78 (2013) 1 (January); p. 44-52)

  • PMID: 23127819
  • DOI: 10.1016/j.steroids.2012.10.008


Abstract

Methyltestosterone (MT) is one of the most frequently detected anabolic androgenic steroids in doping control analysis. MT misuse is commonly detected by the identification of its two main metabolites excreted as glucuronide conjugates, 17α-methyl-5α-androstan-3α,17β-diol and 17α-methyl-5β-androstan-3α,17β-diol. The detection of these metabolites is normally performed by gas chromatography-mass spectrometry, after previous hydrolysis with β-glucuronidase enzymes, extraction and derivatization steps. The aim of the present work was to study the sulphate fraction of MT and to evaluate their potential to improve the detection of the misuse of the drug in sports. MT was administered to healthy volunteers and urine samples were collected up to 30days after administration. After an extraction with ethyl acetate, urine extracts were analysed by liquid chromatography tandem mass spectrometry using electrospray ionisation in negative mode by monitoring the transition m/z 385 to m/z 97. Three diol sulphate metabolites (S1, S2 and S3) were detected. Potential structures for these metabolites were proposed after solvolysis and mass spectrometric experiments: S1, 17α-methyl-5β-androstan-3α,17β-diol 3α-sulphate; S2, 17β-methyl-5α-androstan-3α,17α-diol 3α-sulphate; and S3, 17β-methyl-5β-androstan-3α,17α-diol 3α-sulphate. Synthesis of reference compounds will be required in order to confirm the structures. The retrospectivity of these sulphate metabolites in the detection of MT misuse was compared with the obtained with previously described metabolites. Metabolite S2 was detected up to 21days after MT administration, improving between 2 and 3 times the retrospectivity of the detection compared to the last long-term metabolite of MT previously described, 17α-hydroxy-17β-methylandrostan-4,6-dien-3-one.

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Science
Study
Date
2 November 2012
People
Gómez, C.
Marcos, J.
Pozo, Óscar J.
Segura, Jordi
Ventur, R.
Country
Spain
Language
English
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Institut Hospital de Mar d'Investigacions Mèdiques (IMIM) - Hospital del Mar Medical Research Institute
Universitat Pompeu Fabra (UPF) - Pompeu Fabra University
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Mass spectrometry analysis
Testing method development
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Methyltestosterone
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2 March 2021
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3 March 2021
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