Human liver cocaine esterases: ethanol-mediated formation of ethylcocaine

A new, pharmacologically active metabolite of cocaine, ethylcocaine, has been reported in individuals after concurrent use of cocaine and ethanol. Formation of ethylcocaine may contribute to the common coabuse of these two drugs and the apparent danger of this practice. We have identified a nonspeci...

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Bibliographic Details
Published inThe FASEB journal Vol. 5; no. 12; p. 2735
Main Authors Dean, R A, Christian, C D, Sample, R H, Bosron, W F
Format Journal Article
LanguageEnglish
Published United States 01.09.1991
Subjects
Carboxylic Ester Hydrolases - isolation & purification
Carboxylic Ester Hydrolases - metabolism
Chromatography, Gel
Cocaine - analogs & derivatives
Cocaine - chemistry
Cocaine - metabolism
Ethanol - metabolism
Gas Chromatography-Mass Spectrometry
Humans
Liver - enzymology
Molecular Structure
Molecular Weight
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Summary:A new, pharmacologically active metabolite of cocaine, ethylcocaine, has been reported in individuals after concurrent use of cocaine and ethanol. Formation of ethylcocaine may contribute to the common coabuse of these two drugs and the apparent danger of this practice. We have identified a nonspecific carboxyl-esterase that catalyzes the ethyl transesterification of cocaine to ethylcocaine in the presence of ethanol. In the absence of ethanol, this human liver esterase catalyzes the hydrolysis of cocaine to benzoylecgonine, a metabolite that is inactive as a psychomotor stimulant. A second human liver esterase is also described. This enzyme catalyzes hydrolysis of cocaine to ecgonine methyl ester, also inactive as a stimulant. These two liver esterases may play important roles in regulating the metabolic inactivation of cocaine.
ISSN:0892-6638
DOI:10.1096/fasebj.5.12.1916095