Question

Cocaethylene is a metabolite of cocaine that can be created under particular circumstances. Describe the in vivo synthesis of Cocaethylene in humans.

Answer 1

• Edit

Cocaethylene is the ethyl ester of benzoylecognine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol co-exist in the blood.

Cocaethylene is the byproduct of concurrent consumption of alcohol and cocaine as metabolized by the liver. Normally, metabolism of cocaine produces two primarily biologically inactive metabolites—benzoylecognine and ecgonine methyl ester. The hepatic carboxylesterase is an important part of cocaine's metabolism because it acts as a catalyst for the hydrolysis of cocaine in the liver, which produces these inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, rather than undergoing hydrolysis with water, which results in the production of cocaethylene.

cocaine + H₂O → benzoylecgonine + methanol(with liver carboxypeptidase 1)

benzoylecgonine + ethanol → cocaethylene + H₂O

cocaine + ethanol → cocaethylene + Methanol(with liver carboxylesterase 1)