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
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
| 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 |
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 |
|---|---|---|
| Occupational cocaine exposure of crime laboratory personnel preparing training aids for a military working dog program. | 2003-10 |
|
| 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. | 2003-10 |
|
| Development and validation of a liquid chromatography-mass spectrometry assay for the determination of opiates and cocaine in meconium. | 2003-09-05 |
|
| Prediction of impairment from urine benzoylecgonine concentrations. | 2003-09 |
|
| Sensitivity and specificity of the Cozart microplate EIA cocaine oral fluid at proposed screening and confirmation cutoffs. | 2003-09 |
|
| Quantitation of cocaine and its major metabolites in human saliva using gas chromatography-positive chemical ionization-mass spectrometry (GC-PCI-MS). | 2003-08-12 |
|
| Two new standard reference materials for the determination of drugs of abuse in human hair. | 2003-08 |
|
| Amount of self-reported illicit drug use compared to quantitative hair test results in community-recruited young drug users in Amsterdam. | 2003-07 |
|
| Evaluation of immunochemical drug screenings of whole blood samples. A retrospective optimization of cutoff levels after confirmation-analysis on GC-MS and HPLC-DAD. | 2003-06-25 |
|
| A pilot trial of olanzapine for the treatment of cocaine dependence. | 2003-06-05 |
|
| Cyclodextrin-modified micellar electrokinetic chromatography for the analysis of Esterom, a topical product consisting of hydrolyzed benzoylecgonine in propylene glycol. | 2003-06 |
|
| Intoxication due to 1,4-butanediol. | 2003-05-05 |
|
| The analysis of an intracerebral hematoma for drugs of abuse. | 2003-05 |
|
| Proficiency test for the analysis of hair for drugs of abuse, organized by the Society of Hair Testing. | 2003-04-23 |
|
| Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes. | 2003-04 |
|
| Immunosuppression and oxidative stress induced by acute and chronic exposure to cocaine in rat. | 2003-04 |
|
| A pilot trial of piracetam and ginkgo biloba for the treatment of cocaine dependence. | 2003-04 |
|
| A fatal paramethoxymethamphetamine intoxication. | 2003-03 |
|
| Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs. | 2003-03 |
|
| Measuring outcome in cocaine clinical trials: a comparison of sweat patches with urine toxicology and participant self-report. | 2003-03 |
|
| Comparison of meconium and neonatal hair analysis for detection of gestational exposure to drugs of abuse. | 2003-03 |
|
| Reduction of tissue concentration of cocaine in rat by ketamine. | 2003-02-14 |
|
| High-performance liquid chromatographic determination of cocaine and benzoylecgonine by direct injection of human blood plasma sample into an alkyl-diol-silica (ADS) precolumn. | 2003-02 |
|
| Cocaine-induced endothelin-1-dependent spasm in rabbit basilar artery in vivo. | 2003-02 |
|
| The happy land homicides: 87 deaths due to smoke inhalation. | 2003-01 |
|
| Cocaethylene metabolism and interaction with cocaine and ethanol: role of carboxylesterases. | 2003-01 |
|
| Disposition of cocaine in skin, interstitial fluid, sebum, and stratum corneum. | 2002-12-28 |
|
| Toxic cocaine- and convulsant-induced modification of forced swimming behaviors and their interaction with ethanol: comparison with immobilization stress. | 2002-11-09 |
|
| Simultaneous, quantitative determination of opiates, amphetamines, cocaine and benzoylecgonine in oral fluid by liquid chromatography quadrupole-time-of-flight mass spectrometry. | 2002-11-05 |
|
| An evaluation of the OnTrak Testcup-er on-site urine drug-testing device for drugs commonly encountered from emergency departments. | 2002-10 |
|
| A field evaluation of five on-site drug-testing devices. | 2002-10 |
|
| Detection of cocaine analytes and opiates in nails from postmortem cases. | 2002-10 |
|
| Evaluation of a solid-phase extraction method for benzoylecgonine urine analysis in a high-throughput forensic urine drug-testing laboratory. | 2002-10 |
|
| Urinary elimination of cocaine metabolites in chronic cocaine users during cessation. | 2002-10 |
|
| Analysis of reaction products of cocaine and hydrogen peroxide by high-performance liquid chromatography/mass spectrometry. | 2002-09 |
|
| Hair analysis for opiates, cocaine and metabolites. Evaluation of a method by interlaboratory comparison. | 2002-08-14 |
|
| Endogenous gonadal hormones modulate behavioral and neurochemical responses to acute and chronic cocaine administration. | 2002-07-26 |
|
| One-step liquid-liquid extraction of cocaine from urine samples for gas chromatographic analysis. | 2002-07-17 |
|
| Focused microwave-assisted extraction of cocaine and benzoylecgonine from coca leaves. | 2002-07-09 |
|
| Confirmation of cocaine exposure by gas chromatography-mass spectrometry of urine extracts after methylation of benzoylecgonine. | 2002-06-15 |
|
| Simultaneous screening and detection of drugs in small blood samples and bloodstains. | 2002-05-23 |
|
| Impaired inhibitory control of behavior in chronic cocaine users. | 2002-05-01 |
|
| Drugs of abuse monitoring in blood for control of driving under the influence of drugs. | 2002-04 |
|
| Development and validation of a high-performance liquid chromatography method for the determination of cocaine, its metabolites and ketamine. | 2002-03-29 |
|
| Determination of the highest no-effect dose (HNED) and of the elimination pattern for cocaine in horses. | 2002-03-29 |
|
| Acute behavioral and physiological effects of modafinil in drug abusers. | 2002-03 |
|
| A fatal case of cocaine poisoning in a body packer. | 2002-01 |
|
| 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 |
|
| Effects of benzoylecgonine on the behavior of suckling rats: a preliminary report. | 1992-01 |
Patents
| Substance Class |
Chemical
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| Record UNII |
5353I8I6YS
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Validated (UNII)
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DB01515
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C005618
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DTXSID7046758
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100000085207
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BENZOYLECGONINE
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41001
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m2386
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