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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
Cocaethylene's effects on coronary artery blood flow and cardiac function in a canine model.
2002
Chromatographic methods for the determination of markers of chronic and acute alcohol consumption.
2002 Dec 5
Effects of concurrent use of alcohol and cocaine.
2002 Jul
Simultaneous screening and detection of drugs in small blood samples and bloodstains.
2002 May 23
Detection of cocaine analytes and opiates in nails from postmortem cases.
2002 Oct
Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases.
2003 Jan
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
Effects of chronic naltrexone treatment in rats on place preference and locomotor activation after acute administration of cocaethylene or ethanol plus cocaine.
2004 May
Detection of cocaine and cocaethylene in sweat by solid-phase microextraction and gas chromatography/mass spectrometry.
2004 Nov 5
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
Application of a validated high-performance liquid chromatography-mass spectrometry assay to the analysis of m- and p-hydroxybenzoylecgonine in meconium.
2005 Jun 5
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
Concentration profiles of cocaine, pyrolytic methyl ecgonidine and thirteen metabolites in human blood and urine: determination by gas chromatography-mass spectrometry.
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
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
Development and validation of a gas chromatography-mass spectrometry assay for opiates and cocaine in human teeth.
2006 Feb 24
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
Cocaethylene affects human microvascular endothelial cell p38 mitogen-activated protein kinase activation and nuclear factor-kappaB DNA-binding activity.
2006 Oct
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
Bioanalytical procedures for determination of drugs of abuse in blood.
2007 Aug
Determination of cocaine and cocaethylene in plasma by solid-phase microextraction and gas chromatography-mass spectrometry.
2007 Jan 1
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
Application of a pyroprobe to simulate smoking and metabolic degradation of abused drugs through analytical pyrolysis.
2007 Mar
Excitability constraints on voltage-gated sodium channels.
2007 Sep
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:22 UTC 2023
Edited
by admin
on Fri Dec 15 15:40:22 UTC 2023
Record UNII
FJO3071W5Y
Record Status Validated (UNII)
Record Version
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Name Type Language
COCAETHYLENE
MI  
Common Name English
HOMOCAINE
Common Name English
ETHYLCOCAINE
Code 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 Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
MESH
C066444
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
MERCK INDEX
m3709
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY Merck Index
CAS
529-38-4
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
SMS_ID
100000137653
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID20873213
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
EVMPD
SUB76196
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
PUBCHEM
644006
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
WIKIPEDIA
COCAETHYLENE
Created by admin on Fri Dec 15 15:40:22 UTC 2023 , Edited by admin on Fri Dec 15 15:40:22 UTC 2023
PRIMARY
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