Tetrahydrogestrinone: discovery, synthesis, and detection in urine

Tetrahydrogestrinone: discovery, synthesis, and detection in urine
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DOI:
10.1002/rcm.1495
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发表时间:
2004-01-01
影响因子:
2
通讯作者:
Hatton, CK
Hatton, CK
中科院分区:
化学3区
文献类型:
--
作者:
Catlin, DH;Sekera, MH;Hatton, CK

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在一个用过的注射器的残留物中发现了四氢孕三烯酮(18 α-高孕-4,9,11-三烯-17 β-醇-3-酮或THG),据称该注射器含有一种运动兴奋剂控制尿液检测无法检测到的合成代谢类固醇。以孕三烯酮为原料,经氢化反应合成了THG,并用质谱和核磁共振谱对其结构进行了表征。我们开发和评价了灵敏和特异的液相色谱/串联质谱快速筛查尿样的方法未衍生化THG的LC/MS/MS THG的组合三甲基甲硅烷基醚-肟衍生物的气相色谱/高分辨质谱(GC/HRMS)分析(使用跃迁m/z 313至241和313至159)(使用片段m/z 240.14、254.15、267.16和294.19)。一项狒狒给药研究表明,THG通过尿液排泄。版权所有(C)2004约翰威利父子有限公司。
Tetrahydrogestrinone (18a-homo-pregna-4,9,11-trien-17beta-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 (C) 2004 John Wiley Sons, Ltd.