Research Article

Tetrahydrogestrinone: discovery, synthesis, and detection in urine

  1. Don H. Catlin*,
  2. Michael H. Sekera,
  3. Brian D. Ahrens,
  4. Borislav Starcevic,
  5. Yu-Chen Chang,
  6. Caroline K. Hatton

Article first published online: 11 MAY 2004

DOI: 10.1002/rcm.1495

Issue

Rapid Communications in Mass Spectrometry

Rapid Communications in Mass Spectrometry

Volume 18, Issue 12, pages 1245–1049, 30 June 2004

Additional Information

How to Cite

Catlin, D. H., Sekera, M. H., Ahrens, B. D., Starcevic, B., Chang, Y.-C. and Hatton, C. K. (2004), Tetrahydrogestrinone: discovery, synthesis, and detection in urine. Rapid Commun. Mass Spectrom., 18: 1245–1049. doi: 10.1002/rcm.1495

Author Information

  1. 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.

Publication History

  1. Issue published online: 11 MAY 2004
  2. Article first published online: 11 MAY 2004
  3. Manuscript Revised: 20 APR 2004
  4. Manuscript Accepted: 20 APR 2004
  5. Manuscript Received: 19 MAR 2004

Funded by

  • United States Anti-Doping Agency

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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.

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