Stereochemical composition of clenbuterol residues in edible tissues of swine

A gas chromatography-mass spectrometry method was developed to measure the stereochemical residues of clenbuterol derivatives in edible tissues of swine. Clenbuterol present in tissue extracts was derivatized with phosgene to form elenbuterol oxazolidin-3-one, which was then separated into component enantiomers using a dimethyl beta -cyclodextrin capillary gas chromatographic column. Purified clenbuterol stereoisomers, isolated using published liquid chromatographic techniques, were used to determine stereoisomer elution order, stereoisomer racemization potential, and accuracy of the method. The stereochemical composition of clenbuterol could be measured at tissue concentrations of <2 ppb using the method. The dextrorotatory stereoisomer was the predominant clenbuterol stereoisomer present in edible tissues of hogs slaughtered after withdrawal periods of 0, 3, and 7 days, with a (+)/(-) isomer ratio of about 3:1. The prevalence of the dextrorotatory stereoisomer in edible tissues of hogs at all withdrawal periods suggests that stereoselective processes are occurring during the absorption, distribution, metabolism, and (or) excretion of clenbuterol. The effect of clenbuterol dose on its stereochemical composition in edible tissues is unknown but will be an area of further investigation.