Cocaethylene
From Wikipedia, the free encyclopedia
administrationProduced from ingestion of cocaine and ethanol
- UK: Controlled Drug
- US: Schedule II
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| Other names | benzoylecgonine ethyl ester, ethylbenzoylecgonine, |
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| Routes of administration | Produced from ingestion of cocaine and ethanol |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.164.816 |
| Chemical and physical data | |
| Formula | C18H23NO4 |
| Molar mass | 317.385 g·mol−1 |
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Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver in small amounts when cocaine and ethanol coexist in the blood.[1] Cocaethylene was first synthesized in 1885;[2][3] its side effects were identified in 1989.[4]
Cocaethylene is the byproduct of concurrent consumption of alcohol and cocaine as they are metabolized by the liver. Normally, the hepatic enzyme carboxylesterase catalyzes the hydrolysis of cocaine in the liver, producing two primarily biologically inactive metabolites—benzoylecgonine and ecgonine methyl ester. If ethanol is also present in the liver, a portion of the cocaine undergoes transesterification with ethanol rather than hydrolysis with water, producing cocaethylene.[1]
- cocaine + H2O → benzoylecgonine + methanol (with liver carboxylesterase 1)[5]
- benzoylecgonine + ethanol → cocaethylene + H2O
- cocaine + ethanol → cocaethylene + methanol (with liver carboxylesterase 1)[6]