Glutathione (GSH) and mercapturic acid (NAC) conjugates of AEME were synthesized, and the stereochemistry of the AEME-NAC conjugate was structurally elucidated by NMR and mass spectrometry. AEME and its transesterification product in the presence of ethanol, anhydroecgonine ethyl ester (AEEE), were synthesized from cocaine hydrochloride. Glutathione adducts formed in vivo are metabolized to N-acetylcysteine derivatives by the enzymatically driven mercapturic acid pathway. This electrophilic structure is suggestive of chemical reactivity with ubiquitously occurring cellular nucleophiles, such as glutathione. Pyrolysis of free-base cocaine readily occurs, forming primarily benzoic acid and anhydroecgonine methyl ester (AEME), which structurally contains an alpha,beta-unsaturated carbonyl functional group. Free-base ("crack") cocaine smoking continues to be a popular method of drug abuse in the United States.
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