BCG

3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID


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Chemical Component Summary

Name3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC ACID
SynonymsBENZOYLECGONINE
Identifiers(1R,2R,3S,5S,8S)-8-methyl-3-(phenylcarbonyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylic acid
FormulaC16 H19 N O4
Molecular Weight289.326
TypeNON-POLYMER
Isomeric SMILESC[N@]1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c3ccccc3)C(=O)O
InChIInChI=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
InChIKeyGVGYEFKIHJTNQZ-RFQIPJPRSA-N

Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count4
Bond Count42
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB01515 
NameBenzoylecgonine
Groups
  • experimental
  • illicit
DescriptionBenzoylecgonine is the major metabolite of cocaine. It is formed by hydrolysis of cocaine in the liver, catalysed by carboxylesterases. It is excreted in the urine of cocaine users after processing in the liver. It is the main pharmaceutical ingredient in the investigational drug Esterom, a topical solution used for the relief of muscle pain that is not FDA approved or on the market in the United States. [A18735]
Synonyms
  • (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylic acid
  • (-)-benzoylecgonine
  • Benzoylecgonine
  • Ecgonine benzoate
  • O-benzoylecgonine
Categories
  • Alkaloids
  • Aza Compounds
  • Azabicyclo Compounds
  • Tropanes
CAS number519-09-5

Related Resource References

Resource NameReference
PubChem 448223, 24916772
ChEMBL CHEMBL1231248
ChEBI CHEBI:41001