BENZOYLECGONINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19NO4
Molecular Weight	289.3264
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(O)=O

InChI

InChIKey=GVGYEFKIHJTNQZ-RFQIPJPRSA-N

InChI=1S/C16H19NO4/c1-17-11-7-8-12(17)14(15(18)19)13(9-11)21-16(20)10-5-3-2-4-6-10/h2-6,11-14H,7-9H2,1H3,(H,18,19)/t11-,12+,13-,14+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H19NO4
Molecular Weight	289.3264
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://thcclear.com/benzoylecgonine-guide/

Benzoylecgonine can be found in medical products as a topical muscle relaxer, anesthetic or to relieve muscle pain. It is also a metabolite that is created in the liver after drug use, in particular, the use of cocaine, making it the main compound tested for cocaine use during drug screenings. The legality of this compound is in the grey area. Cocaine is a schedule II drug, but the metabolite is not the drug, it’s a by-product of its use. So detection of actual use is impossible, as its already a metabolite. But the use of cocaine and cocaine based drugs like crack is detected, through this compound. Benzoylecgonine is formed in the liver by the metabolism of cocaine, catalysed by carboxylesterases, and subsequently excreted in the urine. It can be found in the urine for considerably longer than the cocaine itself which is generally cleared out within 5 days

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Effects of benzoylecgonine on the behavior of suckling rats: a preliminary report.	1992 Jan	1348065
Detection of cocaine metabolite in serum and urine: frequency and correlation with medical diagnosis.	2000 May	10767403
Regional distribution of cocaine in postmortem brain of chronic human cocaine users.	2000 Sep	11005179
Cocaine permeability and metabolism in colonic T-84 epithelial cell line.	2001 Dec 21	11811899
The effect of gamma-vinyl-GABA on the consumption of concurrently available oral cocaine and ethanol in the rat.	2001 Feb	11267634
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	11232850
Importance of vacutainer selection in forensic toxicological analysis of drugs of abuse.	2001 Jul-Aug	11499888
Pediatric toxicologic deaths: a 10-year retrospective study.	2001 Jun	11394756
Pharmacokinetics of cocaine in maternal and fetal rhesus monkeys at mid-gestation.	2001 May	11303043
Urine analysis of laboratory personnel preparing cocaine training aids for a military working dog program.	2001 Oct	11599615
Rapid detection of benzoylecgonine in vitreous humor by enzyme immunoassay.	2001 Oct	11599611
Effect of four laboratory decontamination procedures on the quantitative determination of cocaine and metabolites in hair by HPLC-MS.	2001 Oct	11599590
Effects of cocaine and its major metabolites on the HERG-encoded potassium channel.	2001 Oct	11561083
Cocaine long-term administration induces myocardial depressant effects and adrenoceptors desensitization.	2002	12658872
Hair analysis for opiates, cocaine and metabolites. Evaluation of a method by interlaboratory comparison.	2002 Aug 14	12208026
Confirmation of cocaine exposure by gas chromatography-mass spectrometry of urine extracts after methylation of benzoylecgonine.	2002 Jun 15	12015273
Acute behavioral and physiological effects of modafinil in drug abusers.	2002 Mar	11981223
An evaluation of the OnTrak Testcup-er on-site urine drug-testing device for drugs commonly encountered from emergency departments.	2002 Oct	12423007
Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes.	2003 Apr	12731652
Immunosuppression and oxidative stress induced by acute and chronic exposure to cocaine in rat.	2003 Apr	12689662
A pilot trial of piracetam and ginkgo biloba for the treatment of cocaine dependence.	2003 Apr	12628617
Proficiency test for the analysis of hair for drugs of abuse, organized by the Society of Hair Testing.	2003 Apr 23	12742707
Two new standard reference materials for the determination of drugs of abuse in human hair.	2003 Aug	12879199
High-performance liquid chromatographic determination of cocaine and benzoylecgonine by direct injection of human blood plasma sample into an alkyl-diol-silica (ADS) precolumn.	2003 Feb	12610706
Reduction of tissue concentration of cocaine in rat by ketamine.	2003 Feb 14	12521670
Amount of self-reported illicit drug use compared to quantitative hair test results in community-recruited young drug users in Amsterdam.	2003 Jul	12814504
Quantitation of cocaine and its major metabolites in human saliva using gas chromatography-positive chemical ionization-mass spectrometry (GC-PCI-MS).	2003 Jul-Aug	12908939
Cyclodextrin-modified micellar electrokinetic chromatography for the analysis of Esterom, a topical product consisting of hydrolyzed benzoylecgonine in propylene glycol.	2003 Jun	12783453
A pilot trial of olanzapine for the treatment of cocaine dependence.	2003 Jun 5	12757964
A fatal paramethoxymethamphetamine intoxication.	2003 Mar	12935573
Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs.	2003 Mar	12641438
Measuring outcome in cocaine clinical trials: a comparison of sweat patches with urine toxicology and participant self-report.	2003 Mar	12603231
Comparison of meconium and neonatal hair analysis for detection of gestational exposure to drugs of abuse.	2003 Mar	12598495
The analysis of an intracerebral hematoma for drugs of abuse.	2003 May	12762548
Intoxication due to 1,4-butanediol.	2003 May 5	12787662
Evaluation of immunochemical drug screenings of whole blood samples. A retrospective optimization of cutoff levels after confirmation-analysis on GC-MS and HPLC-DAD.	2003 May-Jun	12820742
Occupational cocaine exposure of crime laboratory personnel preparing training aids for a military working dog program.	2003 Oct	14606999
Cozart RapiScan Oral Fluid Drug Testing System: an evaluation of sensitivity, specificity, and efficiency for cocaine detection compared with ELISA and GC-MS following controlled cocaine administration.	2003 Oct	14606993
Prediction of impairment from urine benzoylecgonine concentrations.	2003 Sep	14524346
Sensitivity and specificity of the Cozart microplate EIA cocaine oral fluid at proposed screening and confirmation cutoffs.	2003 Sep	12928231
Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium.	2003 Sep 5	12954379

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

For drug with each melanin subtype, a time course (5,15, 30, 60, and 90 min) was run to determine the amount of time required for binding equilibrium to be reached. Time course samples were run at concentrations of 2 nM for BENZOYLECGONINE.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:10:21 GMT 2023` Edited by `admin` on `Fri Dec 15 17:10:21 GMT 2023`
Record UNII	5353I8I6YS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZOYLECGONINE

Common Name

English

Ecgonine benzoate [WHO-DD]

Common Name

English

3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID

Systematic Name

English

3.BETA.-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID BENZOATE

Common Name

English

BENZOYLECGONINE [MI]

Common Name

English

ECGONINE BENZOATE

Common Name

English

Code System Code Type Description

DRUG BANK

DB01515