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Mass spectrometric identification and characterization of a new long‐term metabolite of metandienone in human urine
Author(s) -
Schänzer Wilhelm,
Geyer Hans,
Fußhöller Gregor,
Halatcheva Natalia,
Kohler Maxie,
Parr MariaKristina,
Guddat Sven,
Thomas Andreas,
Thevis Mario
Publication year - 2006
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2587
Subject(s) - chemistry , metabolite , chromatography , urine , tandem mass spectrometry , mass spectrometry , liquid chromatography–mass spectrometry , excretion , biochemistry
Anabolic‐androgenic steroids are some of the most frequently detected drugs in amateur and professional sports. Doping control laboratories have developed numerous assays enabling the determination of administered drugs and/or their metabolic products that allow retrospectives with respect to pharmacokinetics and excretion profiles of steroids and their metabolites. A new metabolite generated from metandienone has been identified as 18‐nor‐17 β ‐hydroxymethyl,17 α ‐methyl‐androst‐1,4,13‐trien‐3‐one in excretion study urine samples providing a valuable tool for the long‐term detection of metandienone abuse by athletes in sports drug testing. The metabolite was characterized using gas chromatography/(tandem) mass spectrometry, liquid chromatography/tandem mass spectrometry and liquid chromatography/high‐resolution/high‐accuracy (tandem) mass spectrometry by characteristic fragmentation patterns representing the intact 3‐keto‐1,4‐diene structure in combination with typical product ions substantiating the proposed C/D‐ring structure of the steroid metabolite. In addition, structure confirmation was obtained by the analysis of excretion study urine specimens obtained after administration of 17‐CD 3 ‐labeled metandienone providing the deuterated analogue to the newly identified metabolite. 18‐Nor‐17 β ‐hydroxymethyl,17 α ‐methyl‐androst‐1,4,13‐trien‐3‐one was determined in metandienone administration study urine specimens up to 19 days after application of a single dose of 5 mg, hence providing an extended detection period compared with commonly employed strategies. Copyright © 2006 John Wiley & Sons, Ltd.