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Identification
Name Benzoylecgonine
Accession Number DB01515
Type small molecule
Groups illicit, experimental
Description

Benzoylecgonine 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. [Wikipedia]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • (-)-benzoylecgonine
  • BCG
  • BEG
  • Benzoylecgonine hydrate
  • Benzoylecgonine solution
  • Benzoylecogonine
  • Ecgonine benzoate
  • O-benzoyl-(-)-ecgonine
  • O-benzoylecgonine
Brand names Not Available
Brand name mixtures Not Available
Categories
  • Metabolite
CAS number 519-09-5
Weight Average: 289.3264
Monoisotopic: 289.131408101
Chemical Formula C16H19NO4
InChI Key InChIKey=GVGYEFKIHJTNQZ-RFQIPJPRSA-N
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
Plain Text
IUPAC Name
(1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid
SMILES
[H][C@]12CC[C@]([H])([C@H]([C@H](C1)OC(=O)C1=CC=CC=C1)C(O)=O)N2C
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics Not Available
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 195 oC
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 3.82e+00 g/l ALOGPS
logP 1.71 ALOGPS
logP -0.73 ChemAxon Molconvert
logS -1.88 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 66.84 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 76.39 ChemAxon Molconvert
polarizability 29.93 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C10847 Link_out
PubChem Compound 448223 Link_out
PubChem Substance 46508112 Link_out
ChemSpider 395095 Link_out
ChEBI 41001 Link_out
ChEMBL 41001 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Benzoylecgonine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Comments
Drug created on July 31, 2007 07:10 / Updated on October 11, 2011 11:38

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.