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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| 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
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admin
on
Edited
Mon Mar 31 18:05:01 GMT 2025
by
admin
on
Mon Mar 31 18:05:01 GMT 2025
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| Record UNII |
FJO3071W5Y
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Validated (UNII)
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C066444
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m3709
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COCAETHYLENE
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