Structure via PubChem · Public domain (PubChem)
cocaethylene
Sign in to saveCocaethylene (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. Cocaethylene was first synthesized in 1885; its side effects were identified in 1989.
Chemical data
- Formula
- C18H23NO4
- Molecular weight
- 317.4 g/mol
- IUPAC name
- ethyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
- SMILES
- CCOC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1OC(=O)C3=CC=CC=C3
- InChIKey
- NMPOSNRHZIWLLL-XUWVNRHRSA-N
- XLogP
- 2.7
- Polar surface area
- 55.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
523 papers- Cocaethylene: When Cocaine and Alcohol Are Taken Together.Cureus · 2022
- Cocaethylene toxicity.Journal of addictive diseases · 1997
- Forensic Drug Profile: Cocaethylene.Journal of analytical toxicology · 2019
- Cocaine: An Updated Overview on Chemistry, Detection, Biokinetics, and Pharmacotoxicological Aspects including Abuse Pattern.Toxins · 2022
- Cocaethylene cardiotoxicity in emergency department patients with acute drug overdose.Academic emergency medicine : official journal of the Society for Academic Emergency Medicine · 2023
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 317.162708216
Show 4 more facts
- chemical formula
- C₁₈H₂₃NO₄
- canonical SMILES
- CCOC(=O)C1C2CCC(N2C)CC1OC(=O)C3=CC=CC=C3
- subject has role
- dopamine reuptake inhibitor
- isomeric SMILES
- CCOC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1OC(=O)C3=CC=CC=C3
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
7 sectionsContents
- Metabolic production from cocaine
- Physiological effects
- Risks
- Use in research about combined use of cocaine and alcohol
- See also
- References
- Further reading
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. Cocaethylene was first synthesized in 1885; its side effects were identified in 1989.
==Metabolic production from cocaine==
Excerpted from Wikipedia’s “cocaethylene” article, available under the CC BY-SA 4.0 licence.