Unambiguous identification and characterization of a long-term human metabolite of dehydrochloromethyltestosterone

Guro Forsdahl; Thomas Geisendorfer; Lorenz Göschl; Sandra Pfeffer; Peter Gärtner; Mario Thevis; Günter Gmeiner

doi:10.1002/dta.2385

Unambiguous identification and characterization of a long-term human metabolite of dehydrochloromethyltestosterone

Drug Test Anal. 2018 Mar 23. doi: 10.1002/dta.2385. Online ahead of print.

Authors

Guro Forsdahl^{1

2}, Thomas Geisendorfer¹, Lorenz Göschl¹, Sandra Pfeffer¹, Peter Gärtner³, Mario Thevis⁴, Günter Gmeiner¹

Affiliations

¹ Doping Control Laboratory, Seibersdorf Labor GmbH, Seibersdorf, Austria.
² Department of Pharmacy, University of Tromsø - The Arctic University of Norway, Tromsø, Norway.
³ Institute of Applied Synthetic Chemistry, TU Wien, Vienna, Austria.
⁴ Institute of Biochemistry, Center for Preventive Doping Research, German Sport University, Cologne, Germany.

PMID: 29570240
DOI: 10.1002/dta.2385

Abstract

In doping control analysis, the characterization of urinary steroid metabolites is of high interest for a targeted and long-term detection of prohibited anabolic androgenic steroids (AAS). In this work, the structure of a long-term metabolite of dehydrochloromethyltestosterone (DHCMT) was elucidated. Altogether, 8 possible metabolites with a 17α-methyl-17β-hydroxymethyl - structures were synthesized and compared to a major DHCMT long-term metabolite detected in reference urine excretion samples. The confirmed structure of the metabolite was 4α-chloro-18-nor-17β-hydroxymethyl-17α-methyl-5α-androst-13-en-3α-ol.

Keywords: Anabolic androgenic steroids; dehydrochloromethyltestosterone; doping analysis; long-term metabolite; mass spectrometry.