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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 20:24:35 UTC
HMDB IDHMDB0001010
Secondary Accession Numbers
  • HMDB01010
Metabolite Identification
Common NameNicotine imine
DescriptionNicotine imine belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Nicotine imine is considered to be a practically insoluble (in water) and relatively neutral molecule. Nicotine imine has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, nicotine imine is primarily located in the cytoplasm. Nicotine imine participates in a number of enzymatic reactions. In particular, Nicotine imine can be biosynthesized from nicotine through the action of the enzymes cytochrome P450 2A6 and cytochrome P450 2B6. In addition, Nicotine imine can be converted into cotinine through its interaction with the enzyme aldehyde oxidase. In humans, nicotine imine is involved in the nicotine metabolism pathway and the nicotine action pathway.
Structure
Thumb
Synonyms
ValueSource
(S)-1-(Methylene-11C)-2-(3-pyridinyl)-pyrrolidiumHMDB
(S)-1-(Methylene-11C)-2-(3-pyridinyl)pyrrolidiniumHMDB
11C-Nicotine imineHMDB
Nicotine iminiumHMDB
Nicotine-delta 1'-(5')-iminiumHMDB
Nicotine delta 1'(5)' iminium ionMeSH
Chemical FormulaC10H13N2
Average Molecular Weight161.2236
Monoisotopic Molecular Weight161.107873426
IUPAC Name1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium
Traditional Name1-methyl-2-(pyridin-3-yl)-3,4-dihydro-2H-pyrrol-1-ium
CAS Registry Number74710-78-4
SMILES
C[N+]1=CCCC1C1=CC=CN=C1
InChI Identifier
InChI=1S/C10H13N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6-8,10H,3,5H2,1H3/q+1
InChI KeyGTQXYYYOJZZJHL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Pyridine
  • Heteroaromatic compound
  • Pyrroline
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

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 Solubility0.21 g/LALOGPS
logP-2ALOGPS
logP-2.9ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)4.46ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area15.9 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity59.8 m³·mol⁻¹ChemAxon
Polarizability18.14 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-0ge9-3900000000-031e674b4f7ade3be8eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-1467b2a33df3b3f6ae32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-92c1c5fe0d000faa4561View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9700000000-4792328a8ade7540ad76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-f56164d22376a5571748View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-90a5d859971b907f6da1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-90db76b0d90048cdaa0bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDFDB022368
      KNApSAcK IDNot Available
      Chemspider ID418
      KEGG Compound IDNot Available
      BioCyc IDCPD-3186
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN ID5940
      PubChem Compound431
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available