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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:50 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 a strong basic compound (based on its pKa). Within humans, 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 the action of the enzyme aldehyde oxidase. In humans, nicotine imine is involved in nicotine action pathway.
Structure
Data?1582752170
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 ionHMDB
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
Description 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ge9-3900000000-031e674b4f7ade3be8eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-1467b2a33df3b3f6ae32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-92c1c5fe0d000faa4561Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9700000000-4792328a8ade7540ad76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-f56164d22376a5571748Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-90a5d859971b907f6da1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9500000000-90db76b0d90048cdaa0bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022368
KNApSAcK IDNot Available
Chemspider ID418
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5940
PubChem Compound431
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available