Cocaethylene
Chemical compound From Wikipedia, the free encyclopedia
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] In 1885, cocaethylene was first synthesized (according to edition 13 of the Merck Index),[2] and in 1979, cocaethylene's side effects were discovered.[3]
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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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| ECHA InfoCard | 100.164.816 |
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| Formula | C18H23NO4 |
| Molar mass | 317.385 g·mol−1 |
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Metabolic production from cocaine
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—benzoylecgonine and ecgonine methyl ester. The hepatic enzyme 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.[1]
- cocaine + H2O → benzoylecgonine + methanol (with liver carboxylesterase 1)[4]
- benzoylecgonine + ethanol → cocaethylene + H2O
- cocaine + ethanol → cocaethylene + methanol (with liver carboxylesterase 1)[5]
Physiological effects
Summarize
Perspective
Cocaethylene increases the levels of serotonergic, noradrenergic, and dopaminergic neurotransmission in the brain and has a higher affinity for the dopamine transporter than cocaine, but has a lower affinity for the serotonin and norepinephrine transporters.[6][7] These pharmacological properties make cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI; also known as a "triple reuptake inhibitor").[8]
Although it cannot be bought, cocaethylene is largely considered recreational in and of itself, with stimulant, euphoriant, anorectic, sympathomimetic, and local anesthetic properties with a longer duration of action than cocaine.[9][10] A 2000 study by Hart et al. on the effects of intravenous cocaethylene in humans found that "cocaethylene has pharmacological properties in common with cocaine, but is less potent," consistent with prior research.[9]
Risks
While cocaethylene is more dangerous when administered alone, research suggests that the increase in risk from combining cocaine and ethanol is "thought to be due to alcohol decreasing the metabolism of cocaine and, therefore, increasing [...] cocaine concentrations with only a minimal (if any) contribution to an increased risk from the formation of cocaethylene".[11]
Some studies[12][13] suggest that consuming alcohol in combination with cocaine may be more cardiotoxic than cocaine and "it also carries an 18 to 25 fold increase over cocaine alone in risk of immediate death".[10]
See also
References
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