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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:32 UTC
HMDB IDHMDB0001497
Secondary Accession Numbers
  • HMDB01497
Metabolite Identification
Common NameNicotine-1'-N-oxide
DescriptionNicotine-1'-N-oxide 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. In humans, nicotine-1'-N-oxide is involved in the nicotine metabolism pathway. Nicotine-1'-N-oxide has been detected, but not quantified in, several different foods, such as black chokeberries (Photinia melanocarpa), garden onions (Allium cepa), barleys (Hordeum vulgare), gooseberries (Ribes uva-crispa), and highbush blueberries (Vaccinium corymbosum). This could make nicotine-1'-N-oxide a potential biomarker for the consumption of these foods. Nicotine-1'-N-oxide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Nicotine-1'-N-oxide.
Structure
Data?1582752205
Synonyms
ValueSource
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olateChEBI
3-(1-Methyl-1-oxidopyrrolidin-2-yl)pyridineChEBI
Nicotine 1-N-oxideChEBI
1-Methyl-2-(3-pyridyl)-2,3,4,5-tetrahydropyrrol-1-olic acidGenerator
(1's,2's)-Nicotine-n'-oxideHMDB
(2S)-N-Oxide 3-(1-methyl-2-pyrrolidinyl)-pyridineHMDB
1'-Oxide nicotineHMDB
1-Methyl-2-(3-pyridyl)pyrrolidine 1-oxideHMDB
3-(1-Methyl-1-oxido-2-pyrrolidinyl)pyridineHMDB
N-Oxide 3-(1-methyl-2-pyrrolidinyl)pyridineHMDB
N-Oxide-(1-methyl-2-pyrrolidinyl)pyridineHMDB
Nicotine 1'-oxideHMDB
Nicotine n'-oxideHMDB
Nicotine N(1')-oxideHMDB
Nicotine-1'-oxideHMDB, MeSH
Nicotine 1-N-oxide, (R)-isomerMeSH, HMDB
Nicotine 1-N-oxide, dihydrochloride, (S)-isomerMeSH, HMDB
Nicotine 1-N-oxide, (1S-cis)-isomerMeSH, HMDB
Nicotine 1-N-oxide, (1S-trans)-isomerMeSH, HMDB
Nicotine 1-N-oxide, (2S)-isomerMeSH, HMDB
Nicotine 1-N-oxide, 14C-labeled CPDMeSH, HMDB
Nicotine 1-N-oxide, dihydrochloride, (1S-trans)-isomerMeSH, HMDB
Nicotine 1-N-oxide, (1R-cis)-isomerMeSH, HMDB
Nicotine 1-N-oxide, (1R-trans)-isomerMeSH, HMDB
Nicotine 1-N-oxide, (S)-isomerMeSH, HMDB
Nicotine 1-N-oxide, dihydrochloride, (1R-trans)-isomerMeSH, HMDB
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
SMILES
C[N+]1([O-])CCCC1C1=CN=CC=C1
InChI Identifier
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
InChI KeyRWFBQHICRCUQJJ-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
  • 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
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-79 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP1.17HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.6 g/LALOGPS
logP10(-1.1) g/LALOGPS
logP10(0.038) g/LChemAxon
logS10(-1.2) g/LALOGPS
pKa (Strongest Basic)4.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.7 m³·mol⁻¹ChemAxon
Polarizability19.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.41831661259
DarkChem[M-H]-137.41831661259
AllCCS[M+H]+138.38432859911
AllCCS[M-H]-149.48832859911
DeepCCS[M+H]+133.02230932474
DeepCCS[M-H]-130.62630932474
DeepCCS[M-2H]-164.77730932474
DeepCCS[M+Na]+139.26530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Nicotine-1'-N-oxideC[N+]1([O-])CCCC1C1=CN=CC=C12069.1Standard polar33892256
Nicotine-1'-N-oxideC[N+]1([O-])CCCC1C1=CN=CC=C11348.4Standard non polar33892256
Nicotine-1'-N-oxideC[N+]1([O-])CCCC1C1=CN=CC=C11494.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nicotine-1'-N-oxide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-8900000000-b2b7dd335c3a05aa57bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotine-1'-N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nicotine-1'-N-oxide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Nicotine-1'-N-oxide 6V, Positive-QTOFsplash10-00pi-0900000000-43724ee9d877fcb632a32021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Positive-QTOFsplash10-004i-0900000000-c5515911fcd12c368c312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Positive-QTOFsplash10-004l-5900000000-c464534b639004ad3b542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Positive-QTOFsplash10-0uec-9300000000-2a2d1afce79d8998d3b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Negative-QTOFsplash10-004i-0900000000-4f451a2d6c2540a25c952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Negative-QTOFsplash10-004i-0900000000-7b621173e20fa3dd7ce02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Negative-QTOFsplash10-0fb9-7900000000-1d685bcb46ea923561a32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Negative-QTOFsplash10-004i-0900000000-403f45bf7fa5833766622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Negative-QTOFsplash10-004i-0900000000-403f45bf7fa5833766622021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Negative-QTOFsplash10-004i-9000000000-c2850ce6846335b0374d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 10V, Positive-QTOFsplash10-004i-0900000000-d33bcccb60db843c90052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 20V, Positive-QTOFsplash10-03di-1900000000-c1bca04af770521cb8942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nicotine-1'-N-oxide 40V, Positive-QTOFsplash10-0059-9500000000-d593bd18e59fdd3ed2942021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Hair
  • Kidney
  • Liver
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Testis
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 IDFDB022656
KNApSAcK IDNot Available
Chemspider ID396
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound409
PDB IDNot Available
ChEBI ID30734
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:8068568 ]
  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. [PubMed: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. [PubMed: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. [PubMed:16584135 ]
  5. Fang Y, Svoboda KK: Nicotine inhibits myofibroblast differentiation in human gingival fibroblasts. J Cell Biochem. 2005 Aug 15;95(6):1108-19. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:12707003 ]
  12. Nadler JL, Velasco JS, Horton R: Cigarette smoking inhibits prostacyclin formation. Lancet. 1983 Jun 4;1(8336):1248-50. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15971275 ]
  18. Lambers DS, Clark KE: The maternal and fetal physiologic effects of nicotine. Semin Perinatol. 1996 Apr;20(2):115-26. [PubMed:8857697 ]
  19. Hansson L, Choudry NB, Karlsson JA, Fuller RW: Inhaled nicotine in humans: effect on the respiratory and cardiovascular systems. J Appl Physiol (1985). 1994 Jun;76(6):2420-7. [PubMed: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. [PubMed:15272048 ]