Benzoylecgonine

Benzoylecgonine
IUPAC name 3-Benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylic acid
Identifiers
CAS number	519-09-5 Y
ChemSpider	395095 Y
UNII	5353I8I6YS Y
DrugBank	DB01515
KEGG	C10847 Y
ChEBI	CHEBI:41001 Y
Jmol-3D images	{{#if:CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)O|Image 1
SMILES CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)O
InChI 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 Y Key: GVGYEFKIHJTNQZ-RFQIPJPRSA-N Y InChI=1/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 Key: GVGYEFKIHJTNQZ-RFQIPJPRBD
Properties
Molecular formula	C16H19NO4
Molar mass	289.33 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

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 the primary metabolite of cocaine.

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

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]

See also

• Coca alkaloids
• Truxilline
• Dihydrocuscohygrine

References