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 |
|---|---|---|
| Effects of benzoylecgonine on the behavior of suckling rats: a preliminary report. | 1992 Jan |
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| Hair testing for drugs of abuse: evaluation of external cocaine contamination and risk of false positives. | 2001 Dec 1 |
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| Comparison of ELISAs for opiates, methamphetamine, cocaine metabolite, benzodiazepines, phencyclidine, and cannabinoids in whole blood and urine. | 2001 Mar |
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| Effects of cocaine and cocaine metabolites on cardiovascular function in squirrel monkeys. | 2001 Nov 9 |
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| Experience with urine drug testing by the Correctional Service of Canada. | 2001 Sep 15 |
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| Cocaine long-term administration induces myocardial depressant effects and adrenoceptors desensitization. | 2002 |
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| Development and validation of a high-performance liquid chromatography method for the determination of cocaine, its metabolites and ketamine. | 2002 Mar-Apr |
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| Detection of cocaine analytes and opiates in nails from postmortem cases. | 2002 Oct |
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| Evaluation of a solid-phase extraction method for benzoylecgonine urine analysis in a high-throughput forensic urine drug-testing laboratory. | 2002 Oct |
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| Immunosuppression and oxidative stress induced by acute and chronic exposure to cocaine in rat. | 2003 Apr |
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| 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 |
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| A pilot trial of olanzapine for the treatment of cocaine dependence. | 2003 Jun 5 |
|
| Studies on metabolic pathways of cocaine and its metabolites using microsome preparations from rat organs. | 2003 Mar |
|
| Measuring outcome in cocaine clinical trials: a comparison of sweat patches with urine toxicology and participant self-report. | 2003 Mar |
Patents
| Substance Class |
Chemical
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5353I8I6YS
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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 | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
MAJOR
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