Cocaethylene

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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
Identifiers
  • ethyl (2R,3S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
JSmol)
  • O=C(O[C@H]1C[C@H]2N(C)[C@@H]([C@H]1C(=O)OCC)CC2)c3ccccc3

Cocaethylene (ethylbenzoylecgonine) is the

methyl ester of benzoylecgonine. Cocaethylene is formed by the liver 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]

Metabolic production from cocaine

Cocaethylene is the byproduct of concurrent consumption of

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 +
liver carboxylesterase 1)[4]
benzoylecgonine + ethanol → cocaethylene + H2O
cocaine + ethanol → cocaethylene + methanol (with liver carboxylesterase 1)[5]

Physiological effects

Cocaethylene is largely considered a

serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI; also known as a "triple reuptake inhibitor").[citation needed
]

In most users, cocaethylene produces euphoria and has a longer duration of action than cocaine.[6][7] Some studies[8][9] 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".[7] Cocaethylene has a higher affinity for the dopamine transporter than does cocaine, but has a lower affinity for the serotonin and norepinephrine transporters.[10][11]

In McCance-Katz et alia's 1993 study found that cocaethylene "produced greater subjective ratings of 'High' in comparison with administration of cocaine or alcohol alone."[6]

See also

References

  1. ^
    PMID 12485948
    .
  2. PMID 30796807
    .
  3. ^ * Doward J (8 November 2009). "Warning of extra heart dangers from mixing cocaine and alcohol". The Guardian.
  4. ^ "MetaCyc Reaction: 3.1.1". Retrieved 25 January 2016.
  5. ^ "MetaCyc Reaction: [no EC number assigned]". Retrieved 25 January 2016.
  6. ^
    S2CID 25055492
    .
  7. ^
    PMID 9243342
    .
  8. PMID 11229942
    .
  9. PMID 8371143
    .
  10. PMID 8857569
    .
  11. S2CID 6558411
    .

Further reading

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