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.
Casale
J F
JF
Special Testing and Research Laboratory, U.S. DEA, McLean, VA, USA.
Moore
J M
JM
Cooper
D A
DA
D002713:Chlorine / Q000737:chemistry; D003042:Cocaine / Q000737:chemistry*; D003418:Criminology / Q000379:methods*; D005410:Flame Ionization; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012973:Sodium Hypochlorite / Q000737:chemistry*; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry
D014326:Tropanes; D002713:Chlorine; D012973:Sodium Hypochlorite; D003042:Cocaine