Benzoylecgonine
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| Names | |
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| IUPAC name
3-Benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid
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| Identifiers | |
519-09-5  |
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| ChEBI | CHEBI:41001 |
| ChemSpider | 395095 |
| DrugBank | DB01515 |
| Jmol 3D model | Interactive image |
| KEGG | C10847 |
| UNII | 5353I8I6YS |
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| Properties | |
| C16H19NO4 | |
| Molar mass | 289.33 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Benzoylecgonine is a topical analgesic and the main metabolite of cocaine.
Contents
History
Benzoylecgonine is used as the main pharmaceutical ingredient in the prescription drug Esterom, a topical solution used for the relief of muscle pain.
Pharmacokinetics
Chemically, benzoylecgonine is ecgonine benzoate. It is a primary metabolite of cocaine.[1]
Urinalysis
Benzoylecgonine is the compound tested for in most substantive cocaine urinalyses. It is the corresponding carboxylic acid of cocaine, its methyl ester. 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.[citation needed]
Presence in drinking water
Benzoylecgonine is sometimes found in drinking water supplies. 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.[2] 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.[3] A study done in the United Kingdom found traces of benzoylecgonine in the country's drinking water supply, along with carbamazepine (an anticonvulsant) and ibuprofen (a common non-steroidal anti-inflammatory drug), although the study noted that the amount of each compound present was several orders of magnitude lower than the therapeutic dose and therefore did not pose a risk to the population.[4]
Preliminary studies on ecological systems show that benzoylecgonine has potential toxicity issues.[5] Research is being conducted on degradation options such as advanced oxidation and photocatalysis[6] for this metabolite in an effort to reduce concentrations in waste and surface waters. At environmentally relevant concentrations, benzoylecgonine has been shown to have a negative ecological impact.[5]
See also
References
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