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Record Information
Version3.6
Creation Date2007-05-23 05:46:51 UTC
Update Date2013-05-29 19:43:42 UTC
HMDB IDHMDB06406
Secondary Accession NumbersNone
Metabolite Identification
Common NameEcgonine methyl ester
DescriptionEcgonine methyl ester is a major metabolite of cocaine. It is generally not measured by HPLC because it is poorly detectable by UV, and its water solubility makes recovery from urine difficult. Using modified solid-phase extraction procedures, recoveries of 85% for ecgonine methyl ester could be obtained from urine. (PMID:1298401 ).
Structure
Thumb
Synonyms
  1. Methyl ecgonine
Chemical FormulaC10H17NO3
Average Molecular Weight199.2469
Monoisotopic Molecular Weight199.120843415
IUPAC Namemethyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Traditional IUPAC Namemethyl (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Registry Number7143-09-1
SMILES
COC(=O)[C@@H]1C2CCC(C[C@@H]1O)N2C
InChI Identifier
InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6?,7?,8-,9+/m0/s1
InChI KeyQIQNNBXHAYSQRY-ABIFROTESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Heteropolycyclic Compounds
ClassPiperidines
Sub ClassPiperidinecarboxylic Acids and Derivatives
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Tropane alkaloids(KEGG)
  • Tropanes
Substituents
  • Beta Hydroxy Acid
  • Carboxylic Acid Ester
  • Cyclic Alcohol
  • Pyrrolidine
  • Secondary Alcohol
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct ParentPiperidinecarboxylic Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility587 g/LALOGPS
logP0.14ALOGPS
logP-0.21ChemAxon
logS0.47ALOGPS
pKa (strongest acidic)14.6ChemAxon
pKa (strongest basic)9.04ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area49.77ChemAxon
rotatable bond count2ChemAxon
refractivity51.34ChemAxon
polarizability20.82ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.237 +/- 0.0150 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023911
KNApSAcK IDNot Available
Chemspider ID391939
KEGG Compound IDC12448
BioCyc IDNot Available
BiGG ID2267774
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06406
Metagene LinkHMDB06406
METLIN IDNot Available
PubChem Compound443844
PDB IDNot Available
ChEBI ID708640
References
Synthesis ReferenceKline, Richard Harry, Jr. The synthesis and pharmacological activity of 3-arylecgonine methyl ester and 3-carbamoyloxyecgonine methyl ester analogs: probes for the characterization of the dopaminergic cocaine receptor. (1991), 127 pp. CAN 116:21292 AN 1992:21292
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Roy IM, Jefferies TM, Threadgill MD, Dewar GH: Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection. J Pharm Biomed Anal. 1992 Oct-Dec;10(10-12):943-8. Pubmed: 1298401

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Cocaine + Water → Ecgonine methyl ester + Benzoic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (By similarity).
Gene Name:
CES5A
Uniprot ID:
Q6NT32
Molecular weight:
63925.82
General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
Cocaine + Water → Ecgonine methyl ester + Benzoic aciddetails