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 | |
| 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 |
|
| Immunoassay for detection of cocaine/metabolites in oral fluids. | 2001 Jan-Feb |
|
| Importance of vacutainer selection in forensic toxicological analysis of drugs of abuse. | 2001 Jul-Aug |
|
| Effects of cocaine and ethanol on mouse fetuses. | 2001 Jun |
|
| Cocaine, ethanol, and cocaethylene cardiotoxity in an animal model of cocaine and ethanol abuse. | 2001 Mar |
|
| Effects of cocaine and cocaine metabolites on cardiovascular function in squirrel monkeys. | 2001 Nov 9 |
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| Rapid detection of benzoylecgonine in vitreous humor by enzyme immunoassay. | 2001 Oct |
|
| Effect of four laboratory decontamination procedures on the quantitative determination of cocaine and metabolites in hair by HPLC-MS. | 2001 Oct |
|
| Effects of cocaine and its major metabolites on the HERG-encoded potassium channel. | 2001 Oct |
|
| Detection of cocaine and its metabolites in breast milk. | 2001 Sep |
|
| Cocaethylene's effects on coronary artery blood flow and cardiac function in a canine model. | 2002 |
|
| Cocaethylene and heart disease during murine AIDS. | 2002 Jan |
|
| Inhibition of HERG potassium channels by cocaethylene: a metabolite of cocaine and ethanol. | 2002 Jan |
|
| Cardiovascular complications of cocaine use: recent points on cocaethylene toxicity. | 2002 May |
|
| Simultaneous screening and detection of drugs in small blood samples and bloodstains. | 2002 May 23 |
|
| Toxic cocaine- and convulsant-induced modification of forced swimming behaviors and their interaction with ethanol: comparison with immobilization stress. | 2002 Nov 9 |
|
| Detection of cocaine analytes and opiates in nails from postmortem cases. | 2002 Oct |
|
| Human carboxylesterase 1: from drug metabolism to drug discovery. | 2003 Jun |
|
| Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs. | 2003 Mar |
|
| The pharmacology of cocaethylene in humans following cocaine and ethanol administration. | 2003 Nov 24 |
|
| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium. | 2003 Sep 5 |
|
| Local anesthetic effects of cocaethylene and isopropylcocaine on rat peripheral nerves. | 2004 Jan 23 |
|
| The determination of cocaine, benzoylecgonine, and cocaethylene in small-volume oral fluid samples by liquid chromatography-quadrupole-time-of-flight mass spectrometry. | 2004 Nov-Dec |
|
| 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 |
|
| [A proficiency test for hair analysis in detecting drug abuse as an index of the quality of toxicologic analysis]. | 2005 Jul-Sep |
|
| 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 |
|
| 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 |
|
| HPLC-DAD determination of opioids, cocaine and their metabolites in plasma. | 2006 Aug 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 Feb |
|
| Solid-phase microextraction for the determination of cocaine and cocaethylene in human hair by gas chromatography-mass spectrometry. | 2006 Jan 6 |
|
| Determination of opiates and cocaine in hair using automated enzyme immunoassay screening methodologies followed by gas chromatographic-mass spectrometric (GC-MS) confirmation. | 2006 Jun 2 |
|
| Therapeutic options and challenges for substances of abuse. | 2007 |
|
| Identification of cocaine-contaminated hair: perspectives on a paper. | 2007 Apr |
|
| Cocaethylene as a component in illicit cocaine. | 2007 Apr |
|
| Bioanalytical procedures for determination of drugs of abuse in blood. | 2007 Aug |
|
| 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 |
|
| 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 |
|
| Excitability constraints on voltage-gated sodium channels. | 2007 Sep |
|
| 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 |
|
| 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 |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Oct 22 19:48:09 UTC 2019
by
admin
on
Tue Oct 22 19:48:09 UTC 2019
|
| Record UNII |
FJO3071W5Y
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| Record Status |
Validated (UNII)
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| Record Version |
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C066444
Created by
admin on Tue Oct 22 19:48:09 UTC 2019 , Edited by admin on Tue Oct 22 19:48:09 UTC 2019
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PRIMARY | |||
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M3709
Created by
admin on Tue Oct 22 19:48:09 UTC 2019 , Edited by admin on Tue Oct 22 19:48:09 UTC 2019
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PRIMARY | Merck Index | ||
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529-38-4
Created by
admin on Tue Oct 22 19:48:09 UTC 2019 , Edited by admin on Tue Oct 22 19:48:09 UTC 2019
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PRIMARY | |||
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SUB76196
Created by
admin on Tue Oct 22 19:48:09 UTC 2019 , Edited by admin on Tue Oct 22 19:48:09 UTC 2019
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PRIMARY | |||
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644006
Created by
admin on Tue Oct 22 19:48:09 UTC 2019 , Edited by admin on Tue Oct 22 19:48:09 UTC 2019
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PRIMARY | |||
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COCAETHYLENE
Created by
admin on Tue Oct 22 19:48:09 UTC 2019 , Edited by admin on Tue Oct 22 19:48:09 UTC 2019
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PRIMARY |