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Cocaine metabolism in man: identification of four previously unreported cocaine metabolites in human urine.

Cocaine and 11 of its metabolites were identified in a urine specimen from a cocaine user. Four of the metabolites are reported for the first time: ecgonidine, norecgonidine methyl ester, norecgonine methyl ester, and m-hydroxy-benzoylecgonine. The structures of the newly identified metabolites were confirmed by comparison of their gas chromatographic retention times and their electron ionization and chemical ionization mass spectra with the corresponding data obtained on synthesized standards. Other metabolites present were benzoylecgonine, ecgonine methyl ester, ecgonine, ecgonidine methyl ester, norcocaine, p-hydroxycocaine, and m-hydroxycocaine.