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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23NO4
Molecular Weight 317.3795
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAETHYLENE

SMILES

CCOC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC(=O)C3=CC=CC=C3)N2C

InChI

InChIKey=NMPOSNRHZIWLLL-XUWVNRHRSA-N
InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3/t13-,14+,15-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H23NO4
Molecular Weight 317.3795
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Cocaethylene is the ethyl ester of benzoylecgonine. Cocaethylene is formed in the liver after concurrent use of cocaine and alcohol. Cocaethylene works by blocking the dopamine transporter on dopaminergic presynaptic nerve terminals in the brain. It increases dopamine synaptic content, provoking enhanced postsynaptic receptor stimulation, resulting in euphoria, reinforcement, and self-administration. Compared to cocaine, which is a methyl ether of benzoylecgonine, cocaethylene has three to five times larger half-life in plasma. Cocaethylene is associated with seizures, liver damage and compromised the functioning of the immune system. It carries an 18-25 fold increase in risk for immediate death compared to cocaine alone.

Approval Year

PubMed

PubMed

TitleDatePubMed
Rapid induction of behavioral and neurochemical tolerance to cocaethylene, a model compound for agonist therapy of cocaine dependence.
1999 Sep 1
Regional distribution of cocaine in postmortem brain of chronic human cocaine users.
2000 Sep
Crystal structure of a cocaine-binding antibody.
2001 Aug 3
Analysis of cocaethylene, benzoylecgonine and cocaine in human urine by high-performance thin-layer chromatography with ultraviolet detection: a comparison with high-performance liquid chromatography.
2001 Feb 10
Immunoassay for detection of cocaine/metabolites in oral fluids.
2001 Jan-Feb
Ethanol combined with cocaine inhibits amylase release in guinea pig pancreatic lobules.
2001 Jul
Importance of vacutainer selection in forensic toxicological analysis of drugs of abuse.
2001 Jul-Aug
Cocaine, ethanol, and cocaethylene cardiotoxity in an animal model of cocaine and ethanol abuse.
2001 Mar
Development of a screening method for cocaine and cocaine metabolites in urine using solvent microextraction in conjunction with gas chromatography.
2001 Mar 9
Electrophysiological effects of cocaethylene, cocaine, and ethanol on dopaminergic neurons of the ventral tegmental area.
2001 May
Cocaethylene's effects on coronary artery blood flow and cardiac function in a canine model.
2002
Two new standard reference materials for the determination of drugs of abuse in human hair.
2003 Aug
Human carboxylesterase 1: from drug metabolism to drug discovery.
2003 Jun
Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium.
2003 Sep 5
Hair analysis for cocaine: the requirement for effective wash procedures and effects of drug concentration and hair porosity in contamination and decontamination.
2005 Jul-Aug
Analysis of cocaine and three of its metabolites in hair by gas chromatography-mass spectrometry using ion-trap detection for CI/MS/MS.
2005 Nov 5
Application of pericardial fluid to the analysis of morphine (heroin) and cocaine in forensic toxicology.
2006 Dec 20
Simultaneous analyses of cocaine, cocaethylene, and their possible metabolic and pyrolytic products.
2006 Feb 10
Development and validation of a gas chromatography-mass spectrometry assay for opiates and cocaine in human teeth.
2006 Feb 24
Concurrent crack and powder cocaine users from Sao Paulo: do they represent a different group?
2006 Jan 20
Validation of a gas chromatography--ion trap tandem mass spectrometry for simultaneous analyse of cocaine and its metabolites in saliva.
2006 Jun 7
Cocaethylene affects human microvascular endothelial cell p38 mitogen-activated protein kinase activation and nuclear factor-kappaB DNA-binding activity.
2006 Oct
Determination of cocaine and cocaethylene in urine by solid-phase microextraction and gas chromatography-mass spectrometry.
2006 Oct
Alcohol consumption is preferred to water in rats pretreated with intravenous cocaine.
2006 Sep
Identification of cocaine-contaminated hair: perspectives on a paper.
2007 Apr
Determination of cocaine and cocaethylene in plasma by solid-phase microextraction and gas chromatography-mass spectrometry.
2007 Jan 1
Microwave assisted extraction of drugs of abuse from human urine.
2007 Jul-Aug
Validation of a procedure for the gas chromatography-mass spectrometry analysis of cocaine and metabolites in pericardial fluid.
2007 Mar
Determination of cocaine and its metabolites using cation-selective exhaustive injection and sweeping-MEKC.
2008 Nov
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:05:01 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:01 GMT 2025
Record UNII
FJO3071W5Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COCAETHYLENE
MI  
Common Name English
ETHYLCOCAINE
Preferred Name English
HOMOCAINE
Common Name English
O-BENZOYL-L-ECGONINE ETHYL ESTER
Common Name English
J21.586D
Code English
COCAETHYLENE [MI]
Common Name English
ETHYLBENZOYLECGONINE
Common Name English
HOMOCOCAINE
Common Name English
(1R,2R,3S,5S)-3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID ETHYL ESTER
Systematic Name English
Code System Code Type Description
FDA UNII
FJO3071W5Y
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
MESH
C066444
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
MERCK INDEX
m3709
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY Merck Index
CAS
529-38-4
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
SMS_ID
100000137653
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID20873213
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
EVMPD
SUB76196
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
PUBCHEM
644006
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
WIKIPEDIA
COCAETHYLENE
Created by admin on Mon Mar 31 18:05:01 GMT 2025 , Edited by admin on Mon Mar 31 18:05:01 GMT 2025
PRIMARY
Related Record Type Details
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