Physical Sciences and Mathematics Commons^™

Synthesis And Characterization Of D5-Barbarin For Use In Barbarin-Related Research, Sucheta Kudrimoti, Jacob Machin, Adedamola S. Arojojoye, Samuel G. Awuah, Rodney Eisenberg, Clara Fenger, George Maylin, Andreas F. Lehner, Thomas Tobin

Maxwell H. Gluck Equine Research Center Faculty Publications

Based on structural similarities and equine administration experiments, Barbarin, 5-phenyl-2-oxazolidinethione from Brassicaceae plants, is a possible source of equine urinary identifications of aminorex, (R,S)-5-phenyl-4,5-dihydro-1,3-oxazol-2-amine, an amphetamine-related US Drug Enforcement Administration (DEA) controlled substance considered illegal in sport horses. We now report the synthesis and certification of d₅-barbarin to facilitate research on the relationship between plant barbarin and such aminorex identifications. D₅-barbarin synthesis commenced with production of d₅-2-oxo-2-phenylacetaldehyde oxime (d₅-oxime) from d₅-acetophenone via butylnitrite in an ethoxide/ethanol solution. This d₅-oxime was then reduced with lithium aluminum …