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Tetrahydrogestrinone: discovery, synthesis, and detection in urine
Author(s) -
Catlin Don H.,
Sekera Michael H.,
Ahrens Brian D.,
Starcevic Borislav,
Chang YuChen,
Hatton Caroline K.
Publication year - 2004
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.1495
Subject(s) - chemistry , chromatography , urine , mass spectrometry , trimethylsilyl , medicinal chemistry , biochemistry
Tetrahydrogestrinone (18a‐homo‐pregna‐4,9,11‐trien‐17 β ‐ol‐3‐one or THG) was identified in the residue of a spent syringe that had allegedly contained an anabolic steroid undetectable by sport doping control urine tests. THG was synthesized by hydrogenation of gestrinone and characterized by mass spectrometry and NMR spectroscopy. We developed and evaluated sensitive and specific methods for rapid screening of urine samples by liquid chromatography/tandem mass spectrometry (LC/MS/MS) of underivatized THG (using transitions m/z 313 to 241 and 313 to 159) and gas chromatography/high‐resolution mass spectrometry (GC/HRMS) analysis of the combination trimethylsilyl ether‐oxime derivative of THG (using fragments m/z 240.14, 254.15, 267.16, and 294.19). A baboon administration study showed that THG is excreted in urine. Copyright © 2004 John Wiley & Sons, Ltd.