You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:58 UTC
HMDB IDHMDB0001126
Secondary Accession Numbers
  • HMDB01126
Metabolite Identification
Common NameNornicotine
DescriptionNornicotine, also known as (+-)-nornicotine or DL-norcitine, belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. → H 2 O A g 2 O {\displaystyle \mathrm {\xrightarrow[{H_{2}O}]{Ag_{2}O}} } Another route is the partial reduction of 3-myosmine, which can be accomplished by standard catalytic hydrogenation conditions using palladium as a catalyst. There are several routes for the synthesis of nornicotine. Nornicotine is a very strong basic compound (based on its pKa). In humans, nornicotine is involved in nicotine metabolism pathway. or with sodium borohydride This reaction gives the racemic product. It is chemically similar to nicotine, but does not contain a methyl group. It is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco. One route is the demethylation of nicotine, which can be accomplished by reaction with silver oxide. Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant.
Structure
Data?1582752178
Synonyms
ValueSource
(+-)-1'-Demethyl-nicotineHMDB
(+-)-1'-DemethylnicotineHMDB
(+-)-3-(2-Pyrrolidinyl)pyridineHMDB
(+-)-NornicotineHMDB
(R)-3-(Pyrrolidin-2-yl)pyridineHMDB
(R,S)-NornicotineHMDB
(S)-2-(3-Pyridyl)pyrrolidineHMDB
2-(3-Pyridyl)pyrrolidineHMDB
3-(2-Pyrrolidinyl)pyridineHMDB
DL-NorcitineHMDB
L-Nor-nicotineHMDB
NornicotinHMDB
S-(-)-NornicotineHMDB
Nornicotine tartrate, (S)-(R-(r*,r*))-isomerHMDB
Nornicotine, (R)-isomerHMDB
Nornicotine, (S)-isomerHMDB
Chemical FormulaC9H12N2
Average Molecular Weight148.205
Monoisotopic Molecular Weight148.100048394
IUPAC Name3-(pyrrolidin-2-yl)pyridine
Traditional Name(+-)-nornicotine
CAS Registry Number494-97-3
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 KeyMYKUKUCHPMASKF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
  • Aralkylamine
  • Heteroaromatic compound
  • Pyrrolidine
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point270 °CNot Available
Water SolubilityNot AvailableNot Available
LogP0.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility26 g/LALOGPS
logP0.66ALOGPS
logP0.78ChemAxon
logS-0.76ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.36 m³·mol⁻¹ChemAxon
Polarizability16.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1910000000-7aaa8177fe27a116f3e4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1910000000-7aaa8177fe27a116f3e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-4900000000-b1dd2fa89d2e3a6004b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-f2b0fa8b9c12821f2a96Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-f9d65ea20e70d97b17a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-c15db03324adc5374c11Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-0900000000-c74af7c19e9329720e4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0159-0900000000-128439754c8d0a69bec0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001j-0900000000-fbf9379b4dd1ba5915d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001j-0900000000-3268f0d1161f7c767e39Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-1900000000-641ce2610f3b89a02853Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-2900000000-b3d63962e4ee5a7567ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-3900000000-73abee1b55e5f70341cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00lr-5900000000-df09cb3a631636459004Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00lr-9800000000-a45b0ff544bcd0281db0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0159-9300000000-13f626ee37faf5534153Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fsc-9100000000-53e714e4328ef96344a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-59737c2da8553c7ab03fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-c7de13e17b1e82a46e3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v5c-9200000000-8eeb64be10e289cb9303Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-1f7637ef9abf28475e71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-4580e77240a12f45be98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-017l-9500000000-1af339f4c1a6a2b7ae6aSpectrum
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
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.20 (0.01-0.40) umol/mmol creatinineAdult (>18 years old)BothActive tobacco user details
Associated Disorders and Diseases
Disease References
Smoking
  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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022439
KNApSAcK IDC00042792
Chemspider ID21108497
KEGG Compound IDC06524
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNornicotine
METLIN ID1534
PubChem Compound412
PDB IDNot Available
ChEBI ID28313
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferencePapadopoulos, 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 ]
  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 ]
  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 ]
  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 ]
  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 ]