| Benzoylecgonine | |
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3-Benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid |
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| Identifiers | |
| CAS number | 519-09-5 |
| ChemSpider | 395095 |
| UNII | 5353I8I6YS |
| DrugBank | DB01515 |
| KEGG | C10847 |
| ChEBI | CHEBI:41001 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C16H19NO4 |
| Molar mass | 289.33 g mol−1 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Benzoylecgonine is a topical analgesic and the main metabolite of cocaine.
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Benzoylecgonine is used as the main pharmaceutical ingredient in the prescription drug Esterom, a topical solution used for the relief of muscle pain.
Chemically, benzoylecgonine is ecgonine benzoate. It is the primary metabolite of cocaine.
Benzoylecgonine is the compound tested for in most substantive cocaine urinalyses. It is the corresponding carboxylic acid resulting of the hydrolysis of the methyl ester of cocaine. It 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. Small amounts may be traced back to certain OTC (over the counter) medications, after having been metabolized in the liver.
In 2005, scientists found surprisingly large quantities of benzoylecgonine in Italy's Po River and used its concentration to estimate the number of cocaine users in the region.[1] In 2006, a similar study was performed in the Swiss ski town of Saint-Moritz using waste water to estimate the daily cocaine consumption of the population.[2]