Detection of Designer Anabolic Steroids by LC‐MS/MS and Commercial Synthesis of Oxandrolone
Abstract
As of late, the abuse of previously unknown steroids by professional and amateur
athletes has become a major concern for athletic governing bodies. In order to detect
designer steroids, which have been synthesized specifically to evade current analytical
techniques, new analytical screening methods must be devised. For liquid
chromatography‐tandem mass spectrometry at high collision energy, a precursor ion scan
method was proposed, which allows for the detection of potential steroid analytes. The
simultaneous presence of three specific fragmentation ions at m/z 105, 91, and 77 on an
MS spectrum indicates a possible steroid molecule is present in the sample matrix. In
addition to detection, a more efficient commercial‐grade synthesis was investigated
regarding the anabolic steroid, oxandrolone. The Searle procedure was used as a starting
point, for which new reagents were proposed to generate specific reaction intermediates:
α‐bromoketone, enone, and hydroperoxide. Perbromides were used in place of molecular
bromine to brominate the A ring, and an ozonolysis process was used in place of toxic
reagents to oxidize the enone. Together, these mechanistic steps significantly increased
the initial yield from 8% to 45%. At present, there is a constant battle between those
synthesizing designer steroids to evade detection and those developing analytic techniques
able to identify previously unknown steroids.
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