Abstract

17β-Hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one was identified as long-term metabolite of metandienone in human urine resulting in an increased number of adverse analytical findings in doping control for this anabolic steroid within the last few years. As the metabolic fate of the D-ring of other 17-methylated steroids was found to be similar up to now, the excretion of analogous 17-hydroxymethyl-17-methyl-18-norandrost-13-ene derivatives (“night watch”, NW) in human urines after the application of further 17-methyl steroids was studied. Therefore, following single oral doses of the respective steroid, post-administration urines were analysed. After dehydrochloromethyltestosterone (DHCMT), Methyl-1-testosterone and Methyltestosterone administration, the respective derivatives were detected in the glucuronide fraction. From their detection times in the urine, 4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one (after DHCMT) and 17β-hydroxymethyl-17α-methyl-18-nor-5α-androsta-1,13-dien-3-one (after methyl-1-testosterone) may serve for long-term detection in doping control while 17β-hydroxymethyl-17α-methyl-18-norandrosta-4,13-dien-3-one appeared to be excreted only shortly after administration of methyltestosterone. Thus, its detection may only be suitable as supplement in tracing methyltestosterone administration. Also following oxandrolone administration, traces of 17β-hydroxymethyl-17α-methyl-18-nor-2-oxa-5α-androsta-13-en-3-one could be detected in the glucuronide fraction. Following the administration of bolasterone, fluoxymesterone, methandriol, 17-methyl-19-nortestosterone, mibolerone, oxymesterone, and stanozolol no analogous metabolites were so far detected in the urines analysed. The 17-hydroxymethyl-17-methyl-18-norandrost-13-enes are characterised by mass spectrometric techniques. Verf.-Referat