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 |
|---|---|---|
| Occurrence of cocaine in the air of the World's cities. An emerging problem? A new tool to investigate the social incidence of drugs? | 2009-02-15 |
|
| Pharmacodynamic evaluation of the cardiovascular effects after the coadministration of cocaine and ethanol. | 2009-02 |
|
| Cocaine and alcohol: a potential lethal duo. | 2009-01 |
|
| A fast screening MALDI method for the detection of cocaine and its metabolites in hair. | 2009-01 |
|
| Determination of cocaine and its metabolites using cation-selective exhaustive injection and sweeping-MEKC. | 2008-11 |
|
| Comparison of two extraction procedures for determination of drugs of abuse in human saliva by high-performance liquid chromatography. | 2008-11 |
|
| An automated SPE/LC/MS/MS method for the analysis of cocaine and metabolites in whole blood. | 2008-10-15 |
|
| 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. | 2008-10 |
|
| Evidence of temporal cortical dysfunction in rhesus monkeys following chronic cocaine self-administration. | 2008-09 |
|
| 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. | 2008-05 |
|
| Application of discriminant analysis to differentiate between incorporation of cocaine and its congeners into hair and contamination. | 2008-03-21 |
|
| Clinical review: Major consequences of illicit drug consumption. | 2008 |
|
| Determination of cocaine, benzoylecgonine, cocaethylene and norcocaine in human hair using solid-phase extraction and liquid chromatography with tandem mass spectrometric detection. | 2007-11-15 |
|
| Gene expression in human hippocampus from cocaine abusers identifies genes which regulate extracellular matrix remodeling. | 2007-11-14 |
|
| Markers of chronic alcohol use in hair: comparison of ethyl glucuronide and cocaethylene in cocaine users. | 2007-10-02 |
|
| Prevalence and disposition of drugs of abuse and opioid treatment drugs in oral fluid. | 2007-10 |
|
| Excitability constraints on voltage-gated sodium channels. | 2007-09 |
|
| Microwave-assisted extraction and HPLC-DAD determination of drugs of abuse in human plasma. | 2007-09 |
|
| Interest for delivery of cocaethylene in a sustained release emulsion vs saline evaluated on behavioral sensitization in naive and cocaine-sensitized mice. | 2007-08 |
|
| Bioanalytical procedures for determination of drugs of abuse in blood. | 2007-08 |
|
| A simple and reliable procedure for the determination of psychoactive drugs in oral fluid by gas chromatography-mass spectrometry. | 2007-06-28 |
|
| Identification of cocaine-contaminated hair: perspectives on a paper. | 2007-04 |
|
| Cocaethylene as a component in illicit cocaine. | 2007-04 |
|
| Validation of a procedure for the gas chromatography-mass spectrometry analysis of cocaine and metabolites in pericardial fluid. | 2007-03 |
|
| Application of a pyroprobe to simulate smoking and metabolic degradation of abused drugs through analytical pyrolysis. | 2007-03 |
|
| Microwave assisted extraction of drugs of abuse from human urine. | 2007-02-01 |
|
| Short-term efficacy of Disulfiram or Naltrexone in reducing positive urinalysis for both cocaine and cocaethylene in cocaine abusers: a pilot study. | 2007-02 |
|
| Determination of cocaine and cocaethylene in plasma by solid-phase microextraction and gas chromatography-mass spectrometry. | 2007-01-01 |
|
| Therapeutic options and challenges for substances of abuse. | 2007 |
|
| Acute cocaine responses following cocaethylene infusion. | 2007 |
|
| Transcriptional changes common to human cocaine, cannabis and phencyclidine abuse. | 2006-12-27 |
|
| Application of pericardial fluid to the analysis of morphine (heroin) and cocaine in forensic toxicology. | 2006-12-20 |
|
| External contamination of hair with cocaine: evaluation of external cocaine contamination and development of performance-testing materials. | 2006-10 |
|
| Cocaethylene affects human microvascular endothelial cell p38 mitogen-activated protein kinase activation and nuclear factor-kappaB DNA-binding activity. | 2006-10 |
|
| Determination of cocaine and cocaethylene in urine by solid-phase microextraction and gas chromatography-mass spectrometry. | 2006-10 |
|
| Alcohol consumption is preferred to water in rats pretreated with intravenous cocaine. | 2006-09 |
|
| HPLC-DAD determination of opioids, cocaine and their metabolites in plasma. | 2006-08-10 |
|
| Evaluation of solid-phase microextraction desorption parameters for fast GC analysis of cocaine in coca leaves. | 2006-08 |
|
| Validation of a gas chromatography--ion trap tandem mass spectrometry for simultaneous analyse of cocaine and its metabolites in saliva. | 2006-06-07 |
|
| Determination of opiates and cocaine in hair using automated enzyme immunoassay screening methodologies followed by gas chromatographic-mass spectrometric (GC-MS) confirmation. | 2006-06-02 |
|
| Simultaneous quantification of methamphetamine, cocaine, codeine, and metabolites in skin by positive chemical ionization gas chromatography-mass spectrometry. | 2006-04-03 |
|
| Development and validation of a gas chromatography-mass spectrometry assay for opiates and cocaine in human teeth. | 2006-02-24 |
|
| Simultaneous analyses of cocaine, cocaethylene, and their possible metabolic and pyrolytic products. | 2006-02-10 |
|
| A validated positive chemical ionization GC/MS method for the identification and quantification of amphetamine, opiates, cocaine, and metabolites in human postmortem brain. | 2006-02 |
|
| Concurrent crack and powder cocaine users from Sao Paulo: do they represent a different group? | 2006-01-20 |
|
| Solid-phase microextraction for the determination of cocaine and cocaethylene in human hair by gas chromatography-mass spectrometry. | 2006-01-06 |
|
| [A proficiency test for hair analysis in detecting drug abuse as an index of the quality of toxicologic analysis]. | 2005-12-03 |
|
| Analysis of cocaine and three of its metabolites in hair by gas chromatography-mass spectrometry using ion-trap detection for CI/MS/MS. | 2005-11-05 |
|
| Identification of anhydroecgonine ethyl ester in the urine of a drug overdose victim. | 2005-11 |
|
| Hair analysis for cocaine: the requirement for effective wash procedures and effects of drug concentration and hair porosity in contamination and decontamination. | 2005-08-18 |
| Substance Class |
Chemical
Created
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admin
on
Edited
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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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529-38-4
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COCAETHYLENE
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