Structure and properties
Cocaethylene (C18H23NO4, Mr = 317.4 g/mol) is a derivative of cocaine. Unlike cocaine, it contains an ethyl ester rather than a methyl ester.
Formation
Cocaethylene is formed when cocaine and ethanol are consumed simultaneously in the liver by a process called transesterification. The reaction occurs during catalysis by carboxylesterase 1 (hCE1). This enzyme hydrolyzes cocaine to the inactive metabolite benzoylegconine. During transesterification, it uses ethanol instead of water, leading to the formation of cocaethylene.
Effects
Cocaethylene has similar effects to cocaine but a longer half-life of up to two hours. This represents a possible explanation for the mixed use often observed. Ethanol ingestion may inhibit the metabolism and elimination of cocaine. Cocaethylene is more toxic than cocaine.