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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23NO4
Molecular Weight 317.3802
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COCAETHYLENE

SMILES

CCOC(=O)[C@]1([H])[C@@]2([H])CC[C@@]([H])(C[C@]1([H])OC(=O)c3ccccc3)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 317.3802
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
Closing and inactivation potentiate the cocaethylene inhibition of cardiac sodium channels by distinct mechanisms.
2003 Dec
Development of monoclonal antibodies directed against cocaine and cocaethylene: potential new tools for immunotherapy.
2004 Aug
Local anesthetic effects of cocaethylene and isopropylcocaine on rat peripheral nerves.
2004 Jan 23
Evidence for injurious effect of cocaethylene in human microvascular endothelial cells.
2004 Jul
Determination of cocaine, its metabolites, pyrolysis products, and ethanol adducts in postmortem fluids and tissues using Zymark automated solid-phase extraction and gas chromatography-mass spectrometry.
2004 Jul 5
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
Levels of cocaine and its metabolites in washed hair of demonstrated cocaine users and workplace subjects.
2004 Oct 29
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
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
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
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
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
Transcriptional changes common to human cocaine, cannabis and phencyclidine abuse.
2006 Dec 27
Simultaneous analyses of cocaine, cocaethylene, and their possible metabolic and pyrolytic products.
2006 Feb 10
Development and validation of a gas chromatography-mass spectrometry assay for opiates and cocaine in human teeth.
2006 Feb 24
Concurrent crack and powder cocaine users from Sao Paulo: do they represent a different group?
2006 Jan 20
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
Validation of a gas chromatography--ion trap tandem mass spectrometry for simultaneous analyse of cocaine and its metabolites in saliva.
2006 Jun 7
External contamination of hair with cocaine: evaluation of external cocaine contamination and development of performance-testing materials.
2006 Oct
Determination of cocaine and cocaethylene in urine by solid-phase microextraction and gas chromatography-mass spectrometry.
2006 Oct
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
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
Gene expression in human hippocampus from cocaine abusers identifies genes which regulate extracellular matrix remodeling.
2007 Nov 14
Prevalence and disposition of drugs of abuse and opioid treatment drugs in oral fluid.
2007 Oct
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 Sat Jun 26 07:17:59 UTC 2021
Edited
by admin
on Sat Jun 26 07:17:59 UTC 2021
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 Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY
MESH
C066444
Created by admin on Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY
MERCK INDEX
M3709
Created by admin on Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY Merck Index
CAS
529-38-4
Created by admin on Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY
EVMPD
SUB76196
Created by admin on Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY
PUBCHEM
644006
Created by admin on Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY
WIKIPEDIA
COCAETHYLENE
Created by admin on Sat Jun 26 07:18:00 UTC 2021 , Edited by admin on Sat Jun 26 07:18:00 UTC 2021
PRIMARY
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