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Record Information
Version3.6
Creation Date2012-09-13 11:44:28 UTC
Update Date2016-02-11 03:55:37 UTC
HMDB IDHMDB41860
Secondary Accession NumbersNone
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
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 KeyInChIKey=NMPOSNRHZIWLLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Tropane alkaloid
  • Piperidinecarboxylic acid
  • Benzylether
  • Benzoyl
  • N-alkylpyrrolidine
  • Piperidine
  • Dicarboxylic acid or derivatives
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Nutrient
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 mg/mLALOGPS
logP2.53ALOGPS
logP2.64ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.91 m3·mol-1ChemAxon
Polarizability33.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB41860
Metagene LinkHMDB41860
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