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Chemical Compound Review

Nornicotin     3-[(2S)-pyrrolidin-2- yl]pyridine

Synonyms: l-Nor-nicotine, CHEMBL6200, SureCN158146, CHEBI:28313, LS-96492, ...
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Disease relevance of Nornicotin


Psychiatry related information on Nornicotin


High impact information on Nornicotin

  • The possible ingestion and subsequent in vivo nitrosation of nicotine and/or nornicotine could create a serious carcinogenic hazard to cigarette smokers [4].
  • Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase [5].
  • Although each of the six identified members of the P450 family share >90% nucleotide sequence identity, sense expression of three selected isoforms revealed that only one (CYP82E4v1) was involved in the conversion of nicotine to nornicotine [5].
  • Although nornicotine is typically a minor alkaloid in tobacco plants, in many tobacco populations a high percentage of individuals can be found that convert a substantial proportion of the nicotine to nornicotine during leaf senescence and curing [5].
  • Kinetic parameters for nornicotine as well as other related alkaloids were measured and demonstrate that both the pyrrolidine and pyridine rings are critical for optimal catalysis [6].

Biological context of Nornicotin


Anatomical context of Nornicotin


Associations of Nornicotin with other chemical compounds


Gene context of Nornicotin


Analytical, diagnostic and therapeutic context of Nornicotin


  1. Receptor for advanced glycation end product (RAGE) upregulation in human gingival fibroblasts incubated with nornicotine. Katz, J., Caudle, R.M., Bhattacharyya, I., Stewart, C.M., Cohen, D.M. J. Periodontol. (2005) [Pubmed]
  2. Nornicotine pretreatment decreases intravenous nicotine self-administration in rats. Green, T.A., Phillips, S.B., Crooks, P.A., Dwoskin, L.P., Bardo, M.T. Psychopharmacology (Berl.) (2000) [Pubmed]
  3. Acute and chronic effects of nornicotine on locomotor activity in rats: altered response to nicotine. Dwoskin, L.P., Crooks, P.A., Teng, L., Green, T.A., Bardo, M.T. Psychopharmacology (Berl.) (1999) [Pubmed]
  4. Carcinogenicity of N'-nitrosonornicotine in Sprague-Dawley rats. Singer, G.M., Taylor, H.W. J. Natl. Cancer Inst. (1976) [Pubmed]
  5. Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase. Siminszky, B., Gavilano, L., Bowen, S.W., Dewey, R.E. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  6. Aqueous aldol catalysis by a nicotine metabolite. Dickerson, T.J., Janda, K.D. J. Am. Chem. Soc. (2002) [Pubmed]
  7. Effects of nornicotine enantiomers on intravenous S(-)-nicotine self-administration and cardiovascular function in rats. Stairs, D.J., Neugebauer, N.M., Wei, X., Boustany, C., Hojahmat, M., Cassis, L.A., Crooks, P.A., Dwoskin, L.P., Bardo, M.T. Psychopharmacology (Berl.) (2007) [Pubmed]
  8. Contributory role for nornicotine in nicotine neuropharmacology: nornicotine-evoked [3H]dopamine overflow from rat nucleus accumbens slices. Green, T.A., Crooks, P.A., Bardo, M.T., Dwoskin, L.P. Biochem. Pharmacol. (2001) [Pubmed]
  9. Determination of nornicotine in smokers' urine by gas chromatography following reductive alkylation to N'-propylnornicotine. Zhang, Y., Jacob, P., Benowitz, N.L. J. Chromatogr. (1990) [Pubmed]
  10. Determination of the natural abundance delta15N of nicotine and related alkaloids by gas chromatography/isotope ratio mass spectrometry. Molinié, R., Ferchaud-Roucher, V., Lebreton, J., Robins, R.J. Rapid Commun. Mass Spectrom. (2005) [Pubmed]
  11. A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex. Copeland, J.R., Adem, A., Jacob, P., Nordberg, A. Naunyn Schmiedebergs Arch. Pharmacol. (1991) [Pubmed]
  12. Long-lasting occupancy of central nicotinic acetylcholine receptors after smoking: a PET study in monkeys. Valette, H., Bottlaender, M., Dollé, F., Coulon, C., Ottaviani, M., Syrota, A. J. Neurochem. (2003) [Pubmed]
  13. The pharmacological activity of nicotine and nornicotine on nAChRs subtypes: relevance to nicotine dependence and drug discovery. Papke, R.L., Dwoskin, L.P., Crooks, P.A. J. Neurochem. (2007) [Pubmed]
  14. Characterization of hamster liver nicotine metabolism. I. Relative rates of microsomal C and N oxidation. McCoy, G.D., Howard, P.C., DeMarco, G.J. Biochem. Pharmacol. (1986) [Pubmed]
  15. The competition of (-)-[3H]nicotine binding by the enantiomers of nicotine, nornicotine and anatoxin-a in membranes and solubilized preparations of different brain regions of rat. Zhang, X., Nordberg, A. Naunyn Schmiedebergs Arch. Pharmacol. (1993) [Pubmed]
  16. Synthesis and biological characterization of pyridohomotropanes. Structure-activity relationships of conformationally restricted nicotinoids. Kanne, D.B., Abood, L.G. J. Med. Chem. (1988) [Pubmed]
  17. Determination of tobacco alkaloids in single plant cells by capillary electrophoresis. Lochmann, H., Bazzanella, A., Kropsch, S., Bächmann, K. Journal of chromatography. A. (2001) [Pubmed]
  18. Gas chromatographic-mass spectrometric method for determination of anabasine, anatabine and other tobacco alkaloids in urine of smokers and smokeless tobacco users. Jacob, P., Yu, L., Liang, G., Shulgin, A.T., Benowitz, N.L. J. Chromatogr. (1993) [Pubmed]
  19. CYP2A6 AND CYP2B6 are involved in nornicotine formation from nicotine in humans: interindividual differences in these contributions. Yamanaka, H., Nakajima, M., Fukami, T., Sakai, H., Nakamura, A., Katoh, M., Takamiya, M., Aoki, Y., Yokoi, T. Drug Metab. Dispos. (2005) [Pubmed]
  20. Nicotine 5'-oxidation and methyl oxidation by P450 2A enzymes. Murphy, S.E., Raulinaitis, V., Brown, K.M. Drug Metab. Dispos. (2005) [Pubmed]
  21. Competitive inhibition of human placental aromatase by N-n-octanoylnornicotine and other nornicotine derivatives. Bullion, K., Ohnishi, S., Osawa, Y. Endocr. Res. (1991) [Pubmed]
  22. The nicotinic pharmacophore: thermodynamics of the hydrogen-bonding complexation of nicotine, nornicotine, and models. Graton, J., Berthelot, M., Gal, J.F., Laurence, C., Lebreton, J., Le Questel, J.Y., Maria, P.C., Robins, R. J. Org. Chem. (2003) [Pubmed]
  23. Activation of N'-nitrosonornicotine by hydrogen peroxide in vitro. Nair, J., Nair, U.J., Amonkar, A.J., Bhide, S.V. IARC Sci. Publ. (1991) [Pubmed]
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