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Cocaethylene
Systematic (IUPAC) name
ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS number 529-38-4
ATC code none
PubChem 65034
Chemical data
Formula C 18H23NO4  
Mol. mass 317.38 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes from prodrugs cocaine and ethanol

Cocaethylene is the ethyl ester of benzoylecgonine. It is chemically related to cocaine, which is the corresponding methyl ester. Cocaethylene is formed in the body when cocaine and alcohol have been taken simultaneously: the transesterification is catalysed by carboxylesterases in the liver.[1] It does not occur naturally in coca leaves.

Cocaethylene produces a more euphoric stimulation than cocaine in most users, and is longer lasting in the body. Some studies suggest that it may have a higher cardiovascular toxicity than cocaine. Cocaethylene however is less potent at binding to serotonin and norepinephrine transporters than cocaine is.[2][3]

References

  1. ^ S. Casey Laizure, Timothy Mandrell, Naomi M. Gades, and Robert B. Parker (2003). "Cocaethylene Metabolism and Interaction with Cocaine and Ethanol: Role of Carboxylesterases". Drug Metabolism and Disposition 31 (1): 16-20.  
  2. ^ Jatlow, Peter; McCance, Elinore F.; Bradberry, Charles W.; Elsworth, John D.; Taylor, Jane R.; Roth, Robert H. (1996). "Alcohol plus Cocaine: The Whole Is More Than the Sum of Its Parts". Therapeutic Drug Monitoring 18 (4): 460-464. http://journals.lww.com/drug-monitoring/pages/articleviewer.aspx?year=1996&issue=08000&article=00026&type=abstract.  
  3. ^ M. Perez et al. (1994). "Cocaine and cocaethylene: microdialysis comparison of brain drug levels and effects on dopamine and serotonin". Psychopharmacology (Berl.) 116: 428-32. http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=8455033&dopt=Abstract.  

Further reading

See also








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