Gas chromatography/mass spectrometry identification of long-term excreted metabolites of the anabolic steroid 4-chloro-1,2-dehydro-17α-methyltestosterone in humans

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Abstract

The misuse of anabolic steroids by athletes has been banned by sports organizations and is controlled by the analysis of urine samples obtained from athletes using gas chromatography/mass spectrometry (GC/MS). To extend the retrospectivity of the analytical methods, research is focused on long-term excreted metabolites. Preliminary results concerning the long-term detection of metabolites of the anabolic androgenic steroid 4-chloro-1,2-dehydro-17α-methyltestosterone I are presented. A new metabolite 4-chloro-3α,6β,17β-trihydroxy-17α-methyl-5β-androst-1-en-16-one II was isolated by high performance liquid chromatography (HPLC) from urine following a single oral administration of 40 mg of I and characterized. Metabolite II was excreted into urine with a maximum excretion rate at approximately 48 h after administration and could be detected by gas chromatography/high resolution mass spectrometry (GC/HRMS) for up to 14 days. Two further partly characterized metabolites III and IV were confirmed for more than 9 days. The same three metabolites, II-IV, in varying amounts were also detected in urine samples from athletes who administered I.

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    Citation Excerpt :

    Table 1 summarizes the important chromatographic and mass spectrometric data obtained for the TMS derivatives of the DHCMT metabolites; the postulated structures are given in Fig. 2. The metabolite M1, which is fully reduced 16-hydroxylated DHCMT as confirmed by the presence of the ions at m/z 218, 231 in the mass spectrum of its TMS derivative [3] (Fig. 3), is detectable longer that I and II in most cases. The other long-term metabolites are 18-nor-17-hydroxymethyl steroids with the A-ring being partly (M2 and M4) or fully (M3) reduced.

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