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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-03-02 21:26:38 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameNicotine-1'-N-oxide
DescriptionNicotine N'-oxide (NNO) is a primary metabolite of nicotine, although only about 4-7% of nicotine absorbed by smokers is metabolized via this route. The conversion of nicotine to NNO involves a flavin-containing monooxygenase 3 (FMO3). It appears that NNO is not further metabolized to any significant extent, except by reduction back to nicotine, which may lead to recycling of nicotine in the body.
Nicotine 1-N-oxideChEBI
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acidGenerator
(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridineHMDB
1'-Oxide nicotineHMDB
1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxideHMDB
N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridineHMDB
Nicotine 1'-oxideHMDB
Nicotine n'-oxideHMDB
Nicotine N(1')-oxideHMDB
Nicotine 1-N-oxide, (R)-isomerMeSH
Nicotine 1-N-oxide, dihydrochloride, (S)-isomerMeSH
Nicotine 1-N-oxide, (1S-cis)-isomerMeSH
Nicotine 1-N-oxide, (1S-trans)-isomerMeSH
Nicotine 1-N-oxide, (2S)-isomerMeSH
Nicotine 1-N-oxide, 14C-labeled CPDMeSH
Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomerMeSH
Nicotine 1-N-oxide, (1R-cis)-isomerMeSH
Nicotine 1-N-oxide, (1R-trans)-isomerMeSH
Nicotine 1-N-oxide, (S)-isomerMeSH
Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomerMeSH
Chemical FormulaC10H14N2O
Average Molecular Weight178.231
Monoisotopic Molecular Weight178.11061308
IUPAC Name1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate
Traditional Namenicotine 1-N-oxide
CAS Registry Number63551-14-4
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct ParentPyrrolidinylpyridines
Alternative Parents
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • N-alkylpyrrolidine
  • Trialkyl amine oxide
  • Heteroaromatic compound
  • Pyrrolidine
  • Azacycle
  • N-oxide
  • Trisubstituted n-oxide
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Drug metabolite
  • Endogenous
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
Experimental Properties
Melting Point-79 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP1.17HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility11.6 mg/mLALOGPS
pKa (Strongest Basic)4.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.77 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.7 m3·mol-1ChemAxon
Polarizability19.19 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Fetus
  • Fibroblasts
  • Hair
  • Kidney
  • Liver
  • Lung
  • Mouth
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Skin
  • Stratum Corneum
  • Testes
Nicotine Metabolism PathwaySMP00628Not Available
Nicotine PathwaySMP00431Not Available
Normal Concentrations
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00533
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022656
KNApSAcK IDNot Available
Chemspider ID396
KEGG Compound IDNot Available
BioCyc IDCPD-2743
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01497
Metagene LinkHMDB01497
METLIN IDNot Available
PubChem Compound409
PDB IDNot Available
ChEBI ID30734
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  2. Lerman C, Tyndale R, Patterson F, Wileyto EP, Shields PG, Pinto A, Benowitz N: Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. Clin Pharmacol Ther. 2006 Jun;79(6):600-8. Epub 2006 May 11. [16765148 ]
  3. Court JA, Johnson M, Religa D, Keverne J, Kalaria R, Jaros E, McKeith IG, Perry R, Naslund J, Perry EK: Attenuation of Abeta deposition in the entorhinal cortex of normal elderly individuals associated with tobacco smoking. Neuropathol Appl Neurobiol. 2005 Oct;31(5):522-35. [16150123 ]
  4. LeSage MG, Keyler DE, Pentel PR: Current status of immunologic approaches to treating tobacco dependence: vaccines and nicotine-specific antibodies. AAPS J. 2006 Feb 24;8(1):E65-75. [16584135 ]
  5. Fang Y, Svoboda KK: Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. J Cell Biochem. 2005 Aug 15;95(6):1108-19. [15962330 ]
  6. Eliasson B, Smith U, Lonnroth P: No acute effects of smoking and nicotine nasal spray on lipolysis measured by subcutaneous microdialysis. Eur J Clin Invest. 1997 Jun;27(6):503-9. [9229231 ]
  7. Tsurutani J, Castillo SS, Brognard J, Granville CA, Zhang C, Gills JJ, Sayyah J, Dennis PA: Tobacco components stimulate Akt-dependent proliferation and NFkappaB-dependent survival in lung cancer cells. Carcinogenesis. 2005 Jul;26(7):1182-95. Epub 2005 Mar 24. [15790591 ]
  8. Ramachandran J, Rubenstein D, Bluestein D, Jesty J: Activation of platelets exposed to shear stress in the presence of smoke extracts of low-nicotine and zero-nicotine cigarettes: the protective effect of nicotine. Nicotine Tob Res. 2004 Oct;6(5):835-41. [15700919 ]
  9. Miller VM, Lewis DA, Rud KS, Offord KP, Croghan IT, Hurt RD: Plasma nitric oxide before and after smoking cessation with nicotine nasal spray. J Clin Pharmacol. 1998 Jan;38(1):22-7. [9597555 ]
  10. Hureiki J, Laqueille X: [The Tuaregs addiction to tea, to smokeless tobacco and to milk: ethnological and clinical approach] Encephale. 2003 Jan-Feb;29(1):42-8. [12640326 ]
  11. Bonci A, Bernardi G, Grillner P, Mercuri NB: The dopamine-containing neuron: maestro or simple musician in the orchestra of addiction? Trends Pharmacol Sci. 2003 Apr;24(4):172-7. [12707003 ]
  12. Nadler JL, Velasco JS, Horton R: Cigarette smoking inhibits prostacyclin formation. Lancet. 1983 Jun 4;1(8336):1248-50. [6134041 ]
  13. Terry AV Jr, Hernandez CM, Hohnadel EJ, Bouchard KP, Buccafusco JJ: Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. CNS Drug Rev. 2005 Autumn;11(3):229-52. [16389292 ]
  14. Reddy A, Sood A, Rust PF, Busby JE, Varn E, Mathur RS, Mathur S: The effect of nicotine on in vitro sperm motion characteristics. J Assist Reprod Genet. 1995 Mar;12(3):217-23. [8520189 ]
  15. Joshi M, Tyndale RF: Regional and cellular distribution of CYP2E1 in monkey brain and its induction by chronic nicotine. Neuropharmacology. 2006 Apr;50(5):568-75. Epub 2005 Dec 20. [16368115 ]
  16. Marchei E, Durgbanshi A, Rossi S, Garcia-Algar O, Zuccaro P, Pichini S: Determination of arecoline (areca nut alkaloid) and nicotine in hair by high-performance liquid chromatography/electrospray quadrupole mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(22):3416-8. [16259042 ]
  17. Maurer P, Jennings GT, Willers J, Rohner F, Lindman Y, Roubicek K, Renner WA, Muller P, Bachmann MF: A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity. Eur J Immunol. 2005 Jul;35(7):2031-40. [15971275 ]
  18. Lambers DS, Clark KE: The maternal and fetal physiologic effects of nicotine. Semin Perinatol. 1996 Apr;20(2):115-26. [8857697 ]
  19. Hansson L, Choudry NB, Karlsson JA, Fuller RW: Inhaled nicotine in humans: effect on the respiratory and cardiovascular systems. J Appl Physiol. 1994 Jun;76(6):2420-7. [7928866 ]
  20. Warner DO, Joyner MJ, Charkoudian N: Nicotine increases initial blood flow responses to local heating of human non-glabrous skin. J Physiol. 2004 Sep 15;559(Pt 3):975-84. Epub 2004 Jul 22. [15272048 ]