benzoylecgonine
Sign in to saveAlso known as (-)-benzoylecgonine, Benzoylecgonine hydrate, Benzoylecgonine solution, Benzoylecogonine, Ecgonine benzoate, O-benzoyl-(-)-ecgonine, O-benzoylecgonine, (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid
Benzoylecgonine is the main metabolite of cocaine, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens and in wastewater screenings for cocaine use.
Wikidata facts
- Subclass of
- carboxylic acid
- Has part
- hydrogen
- Mass
- 289.131
Show 5 more facts
- chemical formula
- C₁₆H₁₉NO₄
- canonical SMILES
- CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)O
- isomeric SMILES
- CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)O
- Commons category
- Benzoylecgonine
- found in taxon
- Erythroxylum coca
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Biochemistry and physiology
- Urinalysis
- Presence in drinking water
- See also
- References
Benzoylecgonine is the main metabolite of cocaine, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens and in wastewater screenings for cocaine use.
==Biochemistry and physiology== Chemically, benzoylecgonine is the benzoate ester of ecgonine. It is a primary metabolite of cocaine, and is pharmacologically inactive. It is the corresponding carboxylic acid of cocaine, its methyl ester. It is formed in the liver by the metabolism of cocaine by hydrolysis, catalysed by carboxylesterases, and subsequently excreted in the urine. It is readily synthesised by boiling cocaine freebase in water.
Excerpted from Wikipedia’s “benzoylecgonine” article, available under the CC BY-SA 4.0 licence.