Tetrahydrogestrinone: discovery, synthesis, and detection in urine.
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.
Catlin
Don H
DH
UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA. dcatlin@ucla.edu
Sekera
Michael H
MH
Ahrens
Brian D
BD
Starcevic
Borislav
B
Chang
Yu-Chen
YC
Hatton
Caroline K
CK
D000818:Animals; D004300:Doping in Sports; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D005867:Gestrinone / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000302:isolation & purification / Q000652:urine; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D010215:Papio; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013057:Spectrum Analysis / Q000379:methods*
D005867:Gestrinone; C479553:tetrahydrogestrinone