U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Regional distribution of cocaine in postmortem brain of chronic human cocaine users.
2000 Sep
Analysis of cocaethylene, benzoylecgonine and cocaine in human urine by high-performance thin-layer chromatography with ultraviolet detection: a comparison with high-performance liquid chromatography.
2001 Feb 10
Immunoassay for detection of cocaine/metabolites in oral fluids.
2001 Jan-Feb
Development of a screening method for cocaine and cocaine metabolites in urine using solvent microextraction in conjunction with gas chromatography.
2001 Mar 9
Rapid detection of benzoylecgonine in vitreous humor by enzyme immunoassay.
2001 Oct
Effects of cocaine and its major metabolites on the HERG-encoded potassium channel.
2001 Oct
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
Evidence for opponent-process actions of intravenous cocaine and cocaethylene.
2002 Jul
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
Two new standard reference materials for the determination of drugs of abuse in human hair.
2003 Aug
Determination of cocaine, benzoylecgonine and cocaethylene in human hair by solid-phase microextraction and gas chromatography-mass spectrometry.
2003 Dec 25
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
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
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
Evaluation of solid-phase microextraction desorption parameters for fast GC analysis of cocaine in coca leaves.
2006 Aug
Application of pericardial fluid to the analysis of morphine (heroin) and cocaine in forensic toxicology.
2006 Dec 20
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
Concurrent crack and powder cocaine users from Sao Paulo: do they represent a different group?
2006 Jan 20
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
External contamination of hair with cocaine: evaluation of external cocaine contamination and development of performance-testing materials.
2006 Oct
Alcohol consumption is preferred to water in rats pretreated with intravenous cocaine.
2006 Sep
Bioanalytical procedures for determination of drugs of abuse in blood.
2007 Aug
Short-term efficacy of Disulfiram or Naltrexone in reducing positive urinalysis for both cocaine and cocaethylene in cocaine abusers: a pilot study.
2007 Feb
Application of a pyroprobe to simulate smoking and metabolic degradation of abused drugs through analytical pyrolysis.
2007 Mar
Gene expression in human hippocampus from cocaine abusers identifies genes which regulate extracellular matrix remodeling.
2007 Nov 14
Determination of cocaine, benzoylecgonine, cocaethylene and norcocaine in human hair using solid-phase extraction and liquid chromatography with tandem mass spectrometric detection.
2007 Nov 15
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
Microwave-assisted extraction and HPLC-DAD determination of drugs of abuse in human plasma.
2007 Sep
Application of discriminant analysis to differentiate between incorporation of cocaine and its congeners into hair and contamination.
2008 Mar 21
Determination of cocaine and its metabolites using cation-selective exhaustive injection and sweeping-MEKC.
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
Evidence of temporal cortical dysfunction in rhesus monkeys following chronic cocaine self-administration.
2008 Sep
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:22 GMT 2023
Record UNII
FJO3071W5Y
Record Status Validated (UNII)
Record Version
  • Download
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 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
MESH
C066444
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
MERCK INDEX
m3709
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY Merck Index
CAS
529-38-4
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
SMS_ID
100000137653
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
EPA CompTox
DTXSID20873213
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
EVMPD
SUB76196
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
PUBCHEM
644006
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
WIKIPEDIA
COCAETHYLENE
Created by admin on Fri Dec 15 15:40:22 GMT 2023 , Edited by admin on Fri Dec 15 15:40:22 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE