nicotine-1'-N-oxide (PAMDB120186)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120186
Identification
Name: nicotine-1'-N-oxide
Description:Nicotine 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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • nicotine N'-oxide
Chemical Formula: C10H14N2O
Average Molecular Weight: 178.233
Monoisotopic Molecular Weight: 178.11061
InChI Key: RWFBQHICRCUQJJ-NUHJPDEHSA-N
InChI:InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-,12?/m0/s1
CAS number: 63551-14-4
IUPAC Name:1-methyl-2-(pyridin-3-yl)pyrrolidin-1-ium-1-olate
Traditional IUPAC Name: nicotine 1-N-oxide
SMILES:C2(CCC(C1(C=CC=NC=1))N(C)(=O)2)
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct Parent Pyrrolidinylpyridines
Alternative Parents
Substituents
  • 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 Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:0
Melting point: -79 °C
Experimental Properties:
PropertyValueReference
Melting Point-79 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP1.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility11.6 mg/mLALOGPS
logP-1.1ALOGPS
logP0.038ChemAxon
logS-1.2ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
(S)-nicotine + NADPH + Oxygen → nicotine-1'-N-oxide + NADP+ + Water
Pathways: Not Available
Spectra
Spectra: Not Available
References
References:
  • Urakawa N, Nagata T, Kudo K, Kimura K, Imamura T: Simultaneous determination of nicotine and cotinine in various human tissues using capillary gas chromatography/mass spectrometry. Int J Legal Med. 1994;106(5):232-6. [8068568 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • Fang Y, Svoboda KK: Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. J Cell Biochem. 2005 Aug 15;95(6):1108-19. [15962330 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • Nadler JL, Velasco JS, Horton R: Cigarette smoking inhibits prostacyclin formation. Lancet. 1983 Jun 4;1(8336):1248-50. [6134041 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • 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 ]
  • Lambers DS, Clark KE: The maternal and fetal physiologic effects of nicotine. Semin Perinatol. 1996 Apr;20(2):115-26. [8857697 ]
  • 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 ]
  • 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 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
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HMDBHMDB01497
CHEMSPIDER61415
PUBCHEM68107