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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:19 UTC
Secondary Accession Numbers
  • HMDB01411
Metabolite Identification
Common NameCotinine N-oxide
DescriptionCotinine N-oxide is a minor metabolite of nicotine, cotinine formation being the major pathway of nicotine metabolism in smokers. Cotinine N-oxide accounts for less than 5% of the nicotine dose. Cotinine N-oxide can be reduced back to the parent amine in vivo. Nicotine is a naturally occurring alkaloid found in many plants. The principal sources of nicotine exposure are through the use of tobacco, nicotine containing gum and nicotine replacement therapies. Nicotine is an amine composed of pyridine and pyrrolidine rings. It has been shown that nicotine crosses biological membranes and the blood brain barrier easily. The absorbed nicotine is extensively metabolized in the liver to form a wide variety of metabolites including and cotinine N-oxide. Nicotine has been shown to affect a wide variety of biological functions ranging from gene expression, regulation of hormone secretion and enzyme activities. (PMID: 16359169 , 15109883 ).
(-)-Cotinine N-oxideChEBI
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-oxideChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acidGenerator
Chemical FormulaC10H12N2O2
Average Molecular Weight192.2145
Monoisotopic Molecular Weight192.089877638
IUPAC Name3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
Traditional Name3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
CAS Registry Number36508-80-2
InChI Identifier
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
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • Pyridinium
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available


Biological location:


Naturally occurring process:


Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility11 g/LALOGPS
pKa (Strongest Basic)0.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.97 m³·mol⁻¹ChemAxon
Polarizability19.5 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-2900000000-b21511ca6ae8481af0e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-c4eef2387e9f2b62d330Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-fef784f029be5b488c33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmj-4900000000-68e5ea5e4ec111232d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-2aae58a0b3f0a1cfff7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-8a7a6a4c3590431d80baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-db8d337314f54fbc6087Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Normal Concentrations
BloodDetected and Quantified0.000017 +/- 0.000006 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.24 +/- 0.19 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022606
KNApSAcK IDNot Available
Chemspider ID7991264
KEGG Compound IDNot Available
BioCyc IDCPD-3185
BiGG IDNot Available
Wikipedia LinkNot Available
PubChem Compound9815514
PDB IDNot Available
ChEBI ID89087
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceRiah, Omar; Dousset, Jean Claude; Courriere, Philippe; Baziard-Mouysset, Genevieve; Ecalle, Rene. Synthesis of cotinine and cotinine N-oxide. Evaluation of their interaction with nicotine in the insecticidal activity. Natural Product Letters (1997), 11(1), 37-45.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
  2. Jacob P 3rd, Shulgin AT, Yu L, Benowitz NL: Determination of the nicotine metabolite trans-3'-hydroxycotinine in urine of smokers using gas chromatography with nitrogen-selective detection or selected ion monitoring. J Chromatogr. 1992 Dec 2;583(2):145-54. [PubMed:1478978 ]
  3. 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 ]
  4. Brown KM, von Weymarn LB, Murphy SE: Identification of N-(hydroxymethyl) norcotinine as a major product of cytochrome P450 2A6, but not cytochrome P450 2A13-catalyzed cotinine metabolism. Chem Res Toxicol. 2005 Dec;18(12):1792-8. [PubMed:16359169 ]
  5. Yildiz D: Nicotine, its metabolism and an overview of its biological effects. Toxicon. 2004 May;43(6):619-32. [PubMed:15109883 ]