Volume 40, Issue 5 (September 1995)
Novel Chlorinated Tropanes Derived from the Treatment of Cocaine with Sodium Hypochlorite
Several novel chlorinated tropanes were produced when cocaine was treated with aqueous sodium hypochlorite. Two of these, 2′- and 3′-chlorobenzoyloxy-2-carbomethoxypseudotropine (that is, ortho- and meta-chlorococaine), were characterized by synthesis and gas chromatography/mass spectrometry. Four other new chlorinated tropanes (endo-6- and 7-chlorococaine, exo-6- or 7-chlorococaine and N-chlorobenzoylnorecgonine methyl ester) were also tentatively identified via their gas chromatography retention data and mass spectra. The results are of potential use in cocaine signature and comparative analysis.