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Human Metabolome Database Version 3.5

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Showing metabocard for Nornicotine (HMDB01126)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:57 -0700
HMDB ID HMDB01126
Secondary Accession Numbers None
Metabolite Identification
Common Name Nornicotine
Description Nornicotine is an alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (+-)-1'-demethyl-Nicotine
  2. (+-)-1'-Demethylnicotine
  3. (+-)-3-(2-Pyrrolidinyl)pyridine
  4. (+-)-Nornicotine
  5. (R)-3-(Pyrrolidin-2-yl)pyridine
  6. (R,S)-Nornicotine
  7. (S)-2-(3-Pyridyl)pyrrolidine
  8. 2-(3-Pyridyl)pyrrolidine
  9. 3-(2-Pyrrolidinyl)pyridine
  10. Dl-Norcitine
  11. L-Nor-nicotine
  12. Nornicotin
  13. Nornicotine
  14. S-(-)-Nornicotine
Chemical Formula C9H12N2
Average Molecular Weight 148.205
Monoisotopic Molecular Weight 148.100048394
IUPAC Name 3-(pyrrolidin-2-yl)pyridine
Traditional IUPAC Name nornicotine
CAS Registry Number 494-97-3
SMILES C1CNC(C1)C1=CC=CN=C1
InChI Identifier InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2
InChI Key MYKUKUCHPMASKF-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pyrrolidinylpyridines
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Pyridine alkaloids(KEGG)
Substituents
  • Pyridine
  • Pyrrolidine
  • Secondary Aliphatic Amine (Dialkylamine)
Direct Parent Pyrrolidinylpyridines
Ontology
Status Detected and Quantified
Origin
  • Toxin/Pollutant
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point 270 °C Not Available
Water Solubility Not Available Not Available
LogP 0.17 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
LogP 0.66 ALOGPS
LogP 0.78 ChemAxon
LogS -0.76 ALOGPS
pKa (strongest basic) 10.21 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 24.92 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 44.36 ChemAxon
Polarizability 16.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.20 (0.01-0.40) umol/mmol creatinine Adult (>18 years old) Both Active tobacco user Not Available
Associated Disorders and Diseases
Disease References
Smoking
  • Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. Pubmed: 12194923 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022439
    KNApSAcK ID Not Available
    Chemspider ID 21108497 Link_out
    KEGG Compound ID C06524 Link_out
    BioCyc ID CPD-2748 Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB01126 Link_out
    Metagene Link HMDB01126 Link_out
    METLIN ID 1534 Link_out
    PubChem Compound 412 Link_out
    PDB ID Not Available
    ChEBI ID 270347 Link_out
    References
    Synthesis Reference Papadopoulos, Nick M. Formation of nornicotine and other metabolites from nicotine in vitro and in vivo. Canadian Journal of Biochemistry and Physiology (1964), 42(4), 435-42.
    Material Safety Data Sheet (MSDS) Download (PDF)
    General References
    1. Moyer TP, Charlson JR, Enger RJ, Dale LC, Ebbert JO, Schroeder DR, Hurt RD: Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clin Chem. 2002 Sep;48(9):1460-71. Pubmed: 12194923 Link_out
    2. Idris AM, Prokopczyk B, Hoffmann D: Toombak: a major risk factor for cancer of the oral cavity in Sudan. Prev Med. 1994 Nov;23(6):832-9. Pubmed: 7855117 Link_out
    3. Schweinsberg F, Sander J, Schweinsberg E, Kollat P: [Examinations of the possibilities to nitrosate nicotine and nornicotine and of the formation of N-nitrosonornicotine in the stomach of smokers (author's transl)]. Z Krebsforsch Klin Onkol Cancer Res Clin Oncol. 1975 Sep 22;84(1):81-7. Pubmed: 127438 Link_out
    4. Jacob P 3rd, Yu L, Liang G, Shulgin AT, Benowitz NL: Gas chromatographic-mass spectrometric method for determination of anabasine, anatabine and other tobacco alkaloids in urine of smokers and smokeless tobacco users. J Chromatogr. 1993 Sep 8;619(1):49-61. Pubmed: 8245163 Link_out
    5. Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7. Pubmed: 15472033 Link_out