Benzoylecgonine

Benzoylecgonine
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Benzoylecgonine is a topical analgesic and the main metabolite of cocaine.

Contents [hide]
1 History
2 Pharmacokinetics
3 Urinalysis
4 Presence in drinking water
5 See also
6 References

History[edit]
Benzoylecgonine is used as the main pharmaceutical ingredient in the prescription drug Esterom, a topical solution used for the relief of muscle pain.

Pharmacokinetics[edit]
Chemically, benzoylecgonine is ecgonine benzoate. It is a primary metabolite of cocaine.[1]

Urinalysis[edit]
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. Small amounts may be traced back to certain OTC (over the counter) medications, after having been metabolized in the liver.[citation needed]

Presence in drinking water[edit]
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[edit]
Coca alkaloids
Dihydrocuscohygrine
References[edit]
Jump up ^ Schindler, Charles W; Goldberg, Steven R (2012). "Accelerating cocaine metabolism as an approach to the treatment of cocaine abuse and toxicity". Future Medicinal Chemistry 4 (2): 163. doi:10.4155/fmc.11.181. PMID 22300096.
Jump up ^ "Italian river 'full of cocaine'". BBC News. 5 August 2005. Retrieved 11 May 2014.
Jump up ^ "Tant de coke ? Stupéfiant !". Courrier International (in French). 2 February 2006. Retrieved 11 May 2014.
Jump up ^ Withnall, Adam (11 May 2014). "Cocaine use in Britain so high it has contaminated our drinking water, report shows". The Independent. Retrieved 11 May 2014.
^ Jump up to: a b Binelli, A.; Marisa, I.; Federova, M.; Hoffman, R.; Riva, C., A.; Marisa, I; Fedorova, M; Hoffmann, R; Riva, C (2013). "First evidence of protein profile alteration due to the main cocaine metabolite (benzoylecgonine) in a freshwater model". Aquatic Toxicology. 140-141: 268–278. doi:10.1016/j.aquatox.2013.06.013. PMID 23838174.
Jump up ^ Postigo, C.; Sirtori, C.; Oller, I.; Malato, S.; Maldonado, M.I.; Lopez de Alda, M.; Barcelo, D. (2011). "Solar transformation and photocatalytic treatment of cocaine in water: kinetics, characterization of major intermediate products and toxicity evaluation.". Applied Catalysis B: Environmental 104: 37–48.
Categories: Tropane alkaloids found in Erythroxylum cocaHuman metabolitesBenzoatesCarboxylic acids

This page was last modified on 14 December 2014 at 14:04.
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