High Performance Liquid Chromatographic Separation of the Enantiomers and Diastereomers of Primaquine and Its Metabolites

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Abstract
Primaquine, which is marketed as a racemic mixture, was found to be metabolized by microorganisms to a biphenyl dimer, to a methylene linked dimer, and to a sulfur linked dimer. Using a conventional reversed-phase column, the biphenyl dimer could be resolved into three diastereomeric peaks while the methylene linked dimer and the sulfur linked dimer were each resolved into two diasteromeric peaks. Using a chiral Pirkle-1A column, primaquine could be resolved as two peaks, carboxyprimaquine as two peaks, the biphenyl dimer as six peaks, the methylene dimer as three peaks, and the sulfur dimer as three peaks.