Volume 18, Issue 12 p. 1245-1049
Research Article

Tetrahydrogestrinone: discovery, synthesis, and detection in urine

Don H. Catlin

Corresponding Author

Don H. Catlin

UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA

UCLA Olympic Analytical Laboratory, 2122 Granville Avenue, Los Angeles, CA 90025, USA.Search for more papers by this author
Michael H. Sekera

Michael H. Sekera

UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA

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Brian D. Ahrens

Brian D. Ahrens

UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA

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Borislav Starcevic

Borislav Starcevic

UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA

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Yu-Chen Chang

Yu-Chen Chang

UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA

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Caroline K. Hatton

Caroline K. Hatton

UCLA Olympic Analytical Laboratory, Department of Molecular and Medical Pharmacology, University of California at Los Angeles, 2122 Granville Avenue, Los Angeles, CA 90025, USA

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First published: 11 May 2004
Citations: 224

Abstract

Tetrahydrogestrinone (18a-homo-pregna-4,9,11-trien-17β-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.