Cocaethylene

From Wikipedia, the free encyclopedia

Other namesbenzoylecgonine ethyl ester, ethylbenzoylecgonine,
Pregnancy
category
  • C
Routes of
administration
Produced from ingestion of cocaine and ethanol
Cocaethylene
Clinical data
Other namesbenzoylecgonine ethyl ester, ethylbenzoylecgonine,
Pregnancy
category
  • C
Routes of
administration
Produced from ingestion of cocaine and ethanol
Legal status
Legal status
Identifiers
  • ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.164.816 Edit this at Wikidata
Chemical and physical data
FormulaC18H23NO4
Molar mass317.385 g·mol−1
3D model (JSmol)
  • O=C(O[C@H]1C[C@H]2N(C)[C@@H]([C@H]1C(=O)OCC)CC2)c3ccccc3

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 metabolitesbenzoylecgonine 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]

Physiological effects

See also

References

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