The synthesis of deuterium‐labelled cocaine, cocaethylene and metabolites

We describe the syntheses of benzoylecgonine (1,1,1- 2 H 3 )methyl ester [( 2 H 3 ) cocaine], ( 2 H 5 )benzoylecgonine, ( 2 H 5 )benzoylecgonine methyl ester [( 2 H 5 )cocaine], benzoylecgonine (2,2,2- 2 H 3 )ethyl ester [( 2 H 3 )cocaethylene], ( 2 H 5 )benzoylecgonine ethyl ester [( 2 H 5 )cocaethylene], ( 2 H 5 )benzoylecgonine (2,2,2- 2 H 3 )ethyl ester [( 2 H 8 )cocaethylene], ecgonine (1,1,1- 2 H 3 )methyl ester, ecgonine (2,2,2- 2 H 3 )ethyl ester, ecgonine (1,1,2,2,2- 2 H 5 )ethyl ester and anhydroecgonine (1,1,1- 2 H 3 )methyl ester. ( 2 H 5 )Cocaine and ( 2 H 3 )cocaethylene have been administered to human subjects to study the interactions of cocaine and ethanol. The other eight compounds were utilized as analytical standards or internal standards for GC-MS quantitation of cocaine and its metabolites in biological fluids.