Cocaethylene

Cocaethylene
Clinical data
Other namesbenzoylecgonine ethyl ester, ethylbenzoylecgonine,
Pregnancy
category
  • C
Routes of
administration		Produced from ingestion of cocaine and ethanol
ATC code
  • none
Legal status
Legal status
  • UK: Controlled Drug
  • US: Schedule II
Identifiers
IUPAC name
  • 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
Chemical and physical data
FormulaC18H23NO4
Molar mass317.385 g·mol−1
3D model (JSmol)
SMILES
  • 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] 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]

  1. ^ Laizure SC, Mandrell T, Gades NM, Parker RB (January 2003). "Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases". Drug Metabolism and Disposition. 31 (1): 16–20. doi:10.1124/dmd.31.1.16. PMID 12485948.
  2. ^ Jones AW (April 2019). "Forensic Drug Profile: Cocaethylene". Journal of Analytical Toxicology. 43 (3): 155–160. doi:10.1093/jat/bkz007. PMID 30796807.
  3. ^ * Doward J (8 November 2009). "Warning of extra heart dangers from mixing cocaine and alcohol". The Guardian.
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