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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:40:29 UTC
HMDB IDHMDB0001297
Secondary Accession Numbers
  • HMDB01297
Metabolite Identification
Common NameNorcotinine
DescriptionNorcotinine is a metabolite of nicotine. It has been detected in smokers urine (about 1% of total nicotine and metabolites). Two pathways for its formation are possible, demethylation of cotinine or oxidative metabolism of nornicotine. Animal and human studies have demonstrated the existence of both of these pathways.
Structure
Thumb
Synonyms
ValueSource
(RS)-NorcotinineHMDB
5-(3-Pyridinyl)-2-pyrrolidinoneHMDB
DemethylcotinineHMDB
Norcotinine, (+-)-isomerMeSH
Norcotinine, (R)-isomerMeSH
Norcotinine, (S)-isomerMeSH
Chemical FormulaC9H10N2O
Average Molecular Weight162.1885
Monoisotopic Molecular Weight162.079312952
IUPAC Name5-(pyridin-3-yl)pyrrolidin-2-one
Traditional Name5-pyridin-3-ylpyrrolidin-2-one
CAS Registry Number17114-40-8
SMILES
O=C1CCC(N1)C1=CN=CC=C1
InChI Identifier
InChI=1S/C9H10N2O/c12-9-4-3-8(11-9)7-2-1-5-10-6-7/h1-2,5-6,8H,3-4H2,(H,11,12)
InChI KeyFXFANIORDKRCCA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct ParentPyridines and derivatives
Alternative Parents
Substituents
  • Pyridine
  • Heteroaromatic compound
  • Cyclic carboximidic acid
  • Pyrroline
  • Lactim
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane
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 Solubility12.9 mg/mLALOGPS
logP0.13ALOGPS
logP-0.013ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)13.76ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.38 m3·mol-1ChemAxon
Polarizability16.72 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Nicotine Metabolism PathwaySMP00628Not Available
Nicotine PathwaySMP00431Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineExpected but not Quantified Not AvailableNot AvailableNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified0.051 +/- 0.017 uMAdult (>18 years old)BothSmoking details
    Associated Disorders and Diseases
    Disease References
    Smoking
    1. Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00526
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022540
    KNApSAcK IDNot Available
    Chemspider ID400
    KEGG Compound IDNot Available
    BioCyc IDCPD-2749
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0001297
    METLIN ID6142
    PubChem Compound413
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceDewey, Lovell J. Metabolites of nicotine and a synthesis of nornicotine. Journal of the American Chemical Society (1958), 80 1634-6.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
    2. Kyerematen GA, Morgan ML, Chattopadhyay B, deBethizy JD, Vesell ES: Disposition of nicotine and eight metabolites in smokers and nonsmokers: identification in smokers of two metabolites that are longer lived than cotinine. Clin Pharmacol Ther. 1990 Dec;48(6):641-51. [PubMed:2249376 ]
    3. McManus KT, deBethizy JD, Garteiz DA, Kyerematen GA, Vesell ES: A new quantitative thermospray LC-MS method for nicotine and its metabolites in biological fluids. J Chromatogr Sci. 1990 Oct;28(10):510-6. [PubMed:2246349 ]
    4. Kim I, Huestis MA: A validated method for the determination of nicotine, cotinine, trans-3'-hydroxycotinine, and norcotinine in human plasma using solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. J Mass Spectrom. 2006 Jun;41(6):815-21. [PubMed:16705667 ]