The synthesis of deuterium-labelled cocaine, cocaethylene and metabolites

We describe the syntheses of benzoylecgonine (1,1,1-H-2(3))methyl ester [(H -2(3)) cocaine], (H-2(5))benzoylecgonine, (H-2(5))benzoylecgonine methyl es ter [(H-2(5))cocaine], benzoylecgonine (2,2,2-H-2(3))ethyl ester [(H-2(3))c ocaethylene], (H-2(5))benzoylecgonine ethyl ester [(H-2(5))cocaethylene], ( H-2(5))benzoylecgonine (2,2,2-H-2(3))ethyl ester [(H-2(8))cocaethylene], ec gonine(1,1,1 -H-2(3))methyl ester, ecgonine (2,2,2-H-2(3))ethyl ester, ecgo nine(1,1,2,2,2-H-2(5))ethyl eater and anhydroecgonine( 1,1,1-H-2(3))methyl ester. -(H-2(5))Cocaine and (H-2(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 .