Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H19NO4 |
| Molecular Weight | 289.327 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1[C@@]2([H])CC[C@]1([H])[C@]([H])([C@]([H])(C2)OC(=O)c3ccccc3)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
| Molecular Formula | C16H19NO4 |
| Molecular Weight | 289.327 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of benzoylecgonine on the behavior of suckling rats: a preliminary report. | 1992 Jan |
|
| Cocaine permeability and metabolism in colonic T-84 epithelial cell line. | 2001 Dec 21 |
|
| Cocaine long-term administration induces myocardial depressant effects and adrenoceptors desensitization. | 2002 |
|
| Urine toxicology samples in cocaine treatment trials: how many need to be tested? | 2002 |
|
| Drugs of abuse monitoring in blood for control of driving under the influence of drugs. | 2002 Apr |
|
| Hair analysis for opiates, cocaine and metabolites. Evaluation of a method by interlaboratory comparison. | 2002 Aug 14 |
|
| A fatal case of cocaine poisoning in a body packer. | 2002 Jan |
|
| Neonatal hair analysis for benzoylecgonine: a sensitive and semiquantitative biological marker for chronic gestational cocaine exposure. | 2002 Jan |
|
| One-step liquid-liquid extraction of cocaine from urine samples for gas chromatographic analysis. | 2002 Jul 17 |
|
| Endogenous gonadal hormones modulate behavioral and neurochemical responses to acute and chronic cocaine administration. | 2002 Jul 26 |
|
| Confirmation of cocaine exposure by gas chromatography-mass spectrometry of urine extracts after methylation of benzoylecgonine. | 2002 Jun 15 |
|
| Acute behavioral and physiological effects of modafinil in drug abusers. | 2002 Mar |
|
| Indicators of cocaine exposure and preterm birth. | 2002 Mar |
|
| The role of ketamine on plasma cocaine pharmacokinetics in rat. | 2002 Mar 24 |
|
| Development and validation of a high-performance liquid chromatography method for the determination of cocaine, its metabolites and ketamine. | 2002 Mar-Apr |
|
| Determination of the highest no-effect dose (HNED) and of the elimination pattern for cocaine in horses. | 2002 Mar-Apr |
|
| Impaired inhibitory control of behavior in chronic cocaine users. | 2002 May 1 |
|
| Simultaneous screening and detection of drugs in small blood samples and bloodstains. | 2002 May 23 |
|
| Focused microwave-assisted extraction of cocaine and benzoylecgonine from coca leaves. | 2002 May-Jun |
|
| Simultaneous, quantitative determination of opiates, amphetamines, cocaine and benzoylecgonine in oral fluid by liquid chromatography quadrupole-time-of-flight mass spectrometry. | 2002 Nov 5 |
|
| Toxic cocaine- and convulsant-induced modification of forced swimming behaviors and their interaction with ethanol: comparison with immobilization stress. | 2002 Nov 9 |
|
| Disposition of cocaine in skin, interstitial fluid, sebum, and stratum corneum. | 2002 Nov-Dec |
|
| An evaluation of the OnTrak Testcup-er on-site urine drug-testing device for drugs commonly encountered from emergency departments. | 2002 Oct |
|
| A field evaluation of five on-site drug-testing devices. | 2002 Oct |
|
| Detection of cocaine analytes and opiates in nails from postmortem cases. | 2002 Oct |
|
| Evaluation of a solid-phase extraction method for benzoylecgonine urine analysis in a high-throughput forensic urine drug-testing laboratory. | 2002 Oct |
|
| Urinary elimination of cocaine metabolites in chronic cocaine users during cessation. | 2002 Oct |
|
| Analysis of reaction products of cocaine and hydrogen peroxide by high-performance liquid chromatography/mass spectrometry. | 2002 Sep |
|
| Immunosuppression and oxidative stress induced by acute and chronic exposure to cocaine in rat. | 2003 Apr |
|
| A pilot trial of piracetam and ginkgo biloba for the treatment of cocaine dependence. | 2003 Apr |
|
| Two new standard reference materials for the determination of drugs of abuse in human hair. | 2003 Aug |
|
| 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 |
|
| Cocaine-induced endothelin-1-dependent spasm in rabbit basilar artery in vivo. | 2003 Feb |
|
| Reduction of tissue concentration of cocaine in rat by ketamine. | 2003 Feb 14 |
|
| The happy land homicides: 87 deaths due to smoke inhalation. | 2003 Jan |
|
| Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases. | 2003 Jan |
|
| Amount of self-reported illicit drug use compared to quantitative hair test results in community-recruited young drug users in Amsterdam. | 2003 Jul |
|
| Quantitation of cocaine and its major metabolites in human saliva using gas chromatography-positive chemical ionization-mass spectrometry (GC-PCI-MS). | 2003 Jul-Aug |
|
| Cyclodextrin-modified micellar electrokinetic chromatography for the analysis of Esterom, a topical product consisting of hydrolyzed benzoylecgonine in propylene glycol. | 2003 Jun |
|
| A fatal paramethoxymethamphetamine intoxication. | 2003 Mar |
|
| Measuring outcome in cocaine clinical trials: a comparison of sweat patches with urine toxicology and participant self-report. | 2003 Mar |
|
| Comparison of meconium and neonatal hair analysis for detection of gestational exposure to drugs of abuse. | 2003 Mar |
|
| The analysis of an intracerebral hematoma for drugs of abuse. | 2003 May |
|
| Intoxication due to 1,4-butanediol. | 2003 May 5 |
|
| 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 |
|
| Occupational cocaine exposure of crime laboratory personnel preparing training aids for a military working dog program. | 2003 Oct |
|
| 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 |
|
| Prediction of impairment from urine benzoylecgonine concentrations. | 2003 Sep |
|
| Sensitivity and specificity of the Cozart microplate EIA cocaine oral fluid at proposed screening and confirmation cutoffs. | 2003 Sep |
|
| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium. | 2003 Sep 5 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 12:24:31 UTC 2021
by
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on
Sat Jun 26 12:24:31 UTC 2021
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| Record UNII |
5353I8I6YS
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| Record Status |
Validated (UNII)
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DB01515
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C005618
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519-09-5
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BENZOYLECGONINE
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448223
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SUB21920
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208-263-5
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5353I8I6YS
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519-09-5
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M2386
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PRIMARY | Merck Index |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Cocaine is a methyl ester of benzoylecgonine
(an alkaloid found in coca leaves or prepared by synthesis from ecgonine). as per INCB
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| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
