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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
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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
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
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 Tue Oct 22 19:48:09 UTC 2019
Edited
by admin
on Tue Oct 22 19:48:09 UTC 2019
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
MESH
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
CAS
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
PRIMARY
EVMPD
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
PRIMARY
PUBCHEM
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
PRIMARY
WIKIPEDIA
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
PRIMARY