Tetrahydrogestrinone: discovery, synthesis, and detection in urine

Don H Catlin; Michael H Sekera; Brian D Ahrens; Borislav Starcevic; Yu-Chen Chang; Caroline K Hatton

doi:10.1002/rcm.1495

Tetrahydrogestrinone: discovery, synthesis, and detection in urine

Rapid Commun Mass Spectrom. 2004;18(12):1245-049. doi: 10.1002/rcm.1495.

Authors

Don H Catlin¹, Michael H Sekera, Brian D Ahrens, Borislav Starcevic, Yu-Chen Chang, Caroline K Hatton

Affiliation

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. dcatlin@ucla.edu

PMID: 15174177
DOI: 10.1002/rcm.1495

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Doping in Sports*
Gas Chromatography-Mass Spectrometry / methods
Gestrinone* / analogs & derivatives
Gestrinone* / chemical synthesis
Gestrinone* / isolation & purification
Gestrinone* / urine
Humans
Magnetic Resonance Spectroscopy / methods
Male
Papio
Spectrometry, Mass, Electrospray Ionization / methods
Spectrum Analysis / methods*

Substances

Gestrinone
tetrahydrogestrinone