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Record Information
Version4.0
Creation Date2012-09-13 11:44:28 UTC
Update Date2017-09-27 08:33:39 UTC
HMDB IDHMDB0041860
Secondary Accession Numbers
  • HMDB41860
Metabolite Identification
Common NameCocaethylene
DescriptionCocaethylene is a recreational drug with stimulant, euphoriant, anorectic, sympathomimetic and local anesthetic properties. Three monoamine neurotransmitters known as serotonin (5-HT), norepinephrine (NE), and dopamine (DA) play an important role in cocaethylene's action. Cocaethylene increases the level of serotonergic, noradrenergic, and dopaminergic neurotransmission by inhibiting the action of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) which makes cocaethylene a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).[Note 1]; Normally cocaine's metabolism produces two major and biologically inactive metabolites, benzoylecogonine and ecgonine methyl ester. Carboxylesterase is an important part of cocaine's metabolism because it acts as the catalyst for the hydrolysis of cocaine which produces the inactive metabolites. If ethanol is present during the metabolism of cocaine, a portion of the cocaine undergoes transesterification with ethanol, instead of undergoing hydrolysis with water, which results in cocaethylene.
Structure
Thumb
Synonyms
ValueSource
EthylbenzoylecgonineHMDB
HomocaineHMDB
Thylbenzoylecgonine (cocaethylene)HMDB
Coca-ethyleneMeSH
Benzoylecgonine ethyl esterMeSH
EthylcocaineMeSH
Chemical FormulaC18H23NO4
Average Molecular Weight317.3795
Monoisotopic Molecular Weight317.162708229
IUPAC Nameethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Traditional Nameethyl 3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Registry Number529-38-4
SMILES
CCOC(=O)C1C2CCC(CC1OC(=O)C1=CC=CC=C1)N2C
InChI Identifier
InChI=1S/C18H23NO4/c1-3-22-18(21)16-14-10-9-13(19(14)2)11-15(16)23-17(20)12-7-5-4-6-8-12/h4-8,13-16H,3,9-11H2,1-2H3
InChI KeyNMPOSNRHZIWLLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Piperidinecarboxylic acid
  • Tropane alkaloid
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Piperidine
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.16 g/LALOGPS
logP2.53ALOGPS
logP2.64ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.91 m³·mol⁻¹ChemAxon
Polarizability33.98 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0759000000-f20aaaa4f88d5b7cf690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1921000000-1878f9aace099de4a6c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-be7bbb1ffce7c7bc543fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1289000000-b238799d629e81c3c636View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fu-3692000000-c1f442d41b90cc38c257View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-3910000000-a07725f187dbed3eaf87View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00645
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID2723
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia Linkcocaethylene
      METLIN IDNot Available
      PubChem Compound2825
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available