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
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 |
|---|---|---|
| Chromatographic methods for the determination of markers of chronic and acute alcohol consumption. | 2002 Dec 5 |
|
| Two new standard reference materials for the determination of drugs of abuse in human hair. | 2003 Aug |
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| Determination of cocaine, benzoylecgonine and cocaethylene in human hair by solid-phase microextraction and gas chromatography-mass spectrometry. | 2003 Dec 25 |
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| Human carboxylesterase 1: from drug metabolism to drug discovery. | 2003 Jun |
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| Simultaneous detection of some drugs of abuse in saliva samples by SPME technique. | 2003 Jun 24 |
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| Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs. | 2003 Mar |
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| The pharmacology of cocaethylene in humans following cocaine and ethanol administration. | 2003 Nov 24 |
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| Development of monoclonal antibodies directed against cocaine and cocaethylene: potential new tools for immunotherapy. | 2004 Aug |
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| Effects of chronic naltrexone treatment in rats on place preference and locomotor activation after acute administration of cocaethylene or ethanol plus cocaine. | 2004 May |
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| Detection of cocaine and cocaethylene in sweat by solid-phase microextraction and gas chromatography/mass spectrometry. | 2004 Nov 5 |
|
| Levels of cocaine and its metabolites in washed hair of demonstrated cocaine users and workplace subjects. | 2004 Oct 29 |
|
| Effects of seven drugs of abuse on action potential repolarisation in sheep cardiac Purkinje fibres. | 2005 Mar 28 |
|
| Dose-related distribution of codeine, cocaine, and metabolites into human hair following controlled oral codeine and subcutaneous cocaine administration. | 2005 May |
|
| Analysis of opiates, cocaine and metabolites in urine by high-performance liquid chromatography with diode array detection (HPLC-DAD). | 2005 May-Jun |
|
| Identification of anhydroecgonine ethyl ester in the urine of a drug overdose victim. | 2005 Nov |
|
| 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 |
|
| Simultaneous quantification of methamphetamine, cocaine, codeine, and metabolites in skin by positive chemical ionization gas chromatography-mass spectrometry. | 2006 Apr 3 |
|
| Evaluation of solid-phase microextraction desorption parameters for fast GC analysis of cocaine in coca leaves. | 2006 Aug |
|
| HPLC-DAD determination of opioids, cocaine and their metabolites in plasma. | 2006 Aug 10 |
|
| Application of pericardial fluid to the analysis of morphine (heroin) and cocaine in forensic toxicology. | 2006 Dec 20 |
|
| A validated positive chemical ionization GC/MS method for the identification and quantification of amphetamine, opiates, cocaine, and metabolites in human postmortem brain. | 2006 Feb |
|
| Solid-phase microextraction for the determination of cocaine and cocaethylene in human hair by gas chromatography-mass spectrometry. | 2006 Jan 6 |
|
| Validation of a gas chromatography--ion trap tandem mass spectrometry for simultaneous analyse of cocaine and its metabolites in saliva. | 2006 Jun 7 |
|
| Alcohol consumption is preferred to water in rats pretreated with intravenous cocaine. | 2006 Sep |
|
| Therapeutic options and challenges for substances of abuse. | 2007 |
|
| Acute cocaine responses following cocaethylene infusion. | 2007 |
|
| Identification of cocaine-contaminated hair: perspectives on a paper. | 2007 Apr |
|
| Cocaethylene as a component in illicit cocaine. | 2007 Apr |
|
| Interest for delivery of cocaethylene in a sustained release emulsion vs saline evaluated on behavioral sensitization in naive and cocaine-sensitized mice. | 2007 Aug |
|
| Short-term efficacy of Disulfiram or Naltrexone in reducing positive urinalysis for both cocaine and cocaethylene in cocaine abusers: a pilot study. | 2007 Feb |
|
| Microwave assisted extraction of drugs of abuse from human urine. | 2007 Jul-Aug |
|
| A simple and reliable procedure for the determination of psychoactive drugs in oral fluid by gas chromatography-mass spectrometry. | 2007 Jun 28 |
|
| Validation of a procedure for the gas chromatography-mass spectrometry analysis of cocaine and metabolites in pericardial fluid. | 2007 Mar |
|
| Gene expression in human hippocampus from cocaine abusers identifies genes which regulate extracellular matrix remodeling. | 2007 Nov 14 |
|
| Determination of cocaine, benzoylecgonine, cocaethylene and norcocaine in human hair using solid-phase extraction and liquid chromatography with tandem mass spectrometric detection. | 2007 Nov 15 |
|
| Prevalence and disposition of drugs of abuse and opioid treatment drugs in oral fluid. | 2007 Oct |
|
| Markers of chronic alcohol use in hair: comparison of ethyl glucuronide and cocaethylene in cocaine users. | 2007 Oct 2 |
|
| Microwave-assisted extraction and HPLC-DAD determination of drugs of abuse in human plasma. | 2007 Sep |
|
| Clinical review: Major consequences of illicit drug consumption. | 2008 |
|
| Application of discriminant analysis to differentiate between incorporation of cocaine and its congeners into hair and contamination. | 2008 Mar 21 |
|
| Tropane ethyl esters in illicit cocaine: isolation, detection, and determination of new manufacturing by-products from the clandestine purification of crude cocaine base with ethanol. | 2008 May |
|
| Determination of cocaine and its metabolites using cation-selective exhaustive injection and sweeping-MEKC. | 2008 Nov |
|
| Comparison of two extraction procedures for determination of drugs of abuse in human saliva by high-performance liquid chromatography. | 2008 Nov |
|
| Complete automation of solid-phase extraction with subsequent liquid chromatography-tandem mass spectrometry for the quantification of benzoylecgonine, m-hydroxybenzoylecgonine, p-hydroxybenzoylecgonine, and norbenzoylecgonine in urine--application to a high-throughput urine analysis laboratory. | 2008 Oct |
|
| An automated SPE/LC/MS/MS method for the analysis of cocaine and metabolites in whole blood. | 2008 Oct 15 |
|
| Evidence of temporal cortical dysfunction in rhesus monkeys following chronic cocaine self-administration. | 2008 Sep |
|
| Pharmacodynamic evaluation of the cardiovascular effects after the coadministration of cocaine and ethanol. | 2009 Feb |
|
| Occurrence of cocaine in the air of the World's cities. An emerging problem? A new tool to investigate the social incidence of drugs? | 2009 Feb 15 |
|
| Cocaine and alcohol: a potential lethal duo. | 2009 Jan |
|
| A fast screening MALDI method for the detection of cocaine and its metabolites in hair. | 2009 Jan |
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FJO3071W5Y
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C066444
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m3709
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529-38-4
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100000137653
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DTXSID20873213
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SUB76196
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644006
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COCAETHYLENE
Created by
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PARENT (METABOLITE)
SUBSTANCE RECORD
