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Chemical Compound Review

Habitrol     3-(1-methylpyrrolidin-2- yl)pyridine

Synonyms: Nicocide, Nicotina, Nikotyna, Fumetobac, Nicorette, ...
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Disease relevance of nicotine


Psychiatry related information on nicotine

  • In the future, people who continue to smoke will be individuals with severe nicotine dependence or psychiatric symptoms; thus, clinicians will increasingly be called on to provide pharmacotherapy for smoking cessation [4].
  • Pharmacotherapies for tobacco dependence include nicotine replacement medications in the form of gum, transdermal patch, lozenge, sublingual tablet, nasal spray, and vapor inhaler formulations [5].
  • Five medications--bupropion, nicotine gum, nicotine inhaler, nicotine nasal spray, and nicotine patch--and one proven psychosocial therapy (behavior therapy) appear equally effective and safe; i.e., they all double quit rates and are associated with a less than 5% dropout rate due to adverse events [4].
  • This study examined whether the nicotine-induced increase in the metabolic rate observed at rest is also present during physical activity [1].
  • This AChBP structure is relevant for the development of drugs against, for example, Alzheimer's disease and nicotine addiction [6].

High impact information on nicotine


Chemical compound and disease context of nicotine

  • A controlled trial of sustained-release bupropion, a nicotine patch, or both for smoking cessation [10].
  • If higher cotinine levels among blacks indicate higher nicotine intake or differential pharmacokinetics and possibly serve as a marker of higher exposure to cigarette carcinogenic components, they may help explain why blacks find it harder to quit and are more likely to experience higher rates of lung cancer than white smokers [11].
  • In choriocarcinoma cell cultures, nicotine, cotinine (a major metabolite of nicotine), and anabasine (a minor component of cigarette tobacco) all inhibited androstenedione conversion to estrogen in a dose-dependent fashion [12].
  • Tachygastria (> 4.5 cycle/min) increased from 2% +/- 2% to 16% +/- 3% of recording time, and arrhythmias (frequency instability index) increased from 0.5 +/- 0.1 to 1.1 +/- 0.2 cycle/min with nicotine in nonsmokers (P < 0.05), which normalized with indomethacin [13].
  • METHODS: Twenty subjects (9 smokers and 11 nonsmokers) participated in 4 laboratory sessions during which they were challenged with 0, 0.8, 1.6, or 3.2 mg/70 kg of naloxone and then monitored for 1 hour for subjective signs and symptoms of opiate-like withdrawal, nicotine craving, and alterations in cortisol levels [14].

Biological context of nicotine

  • The excess energy expenditure attributable to nicotine was more than twice as great during exercise (difference between groups, 0.51 kJ per kilogram per hour, or 12.1 percent of the metabolic rate at rest; P less than 0.001) than during rest (0.23 kJ per kilogram per hour, or 5.3 percent of the metabolic rate at rest; P less than 0.05) [1].
  • We conclude that the relatively small metabolic effect of nicotine when the subject is at rest is enhanced during light exercise [1].
  • We report here that high-affinity binding sites for nicotine are absent from the brains of mice homozygous for the beta 2-subunit mutation [15].
  • Hippocampal synaptic transmission enhanced by low concentrations of nicotine [16].
  • Neurobiology: memories of nicotine [17].

Anatomical context of nicotine

  • To test the hypothesis that the reduction in tar and nicotine content of cigarette smoke that began in the 1950s should be reflected by the histologic changes in the bronchial epithelium of cigarette smokers, 20, 424 sections taken at autopsy from the bronchial tubes of 445 men (non-lung-cancer deaths) were examined microscopically in random order [18].
  • Nicotine is known to act on presynaptic nAChRs within the habenula of chick to enhance glutamatergic transmission; here we report that a similar mechanism operates in the hippocampus [16].
  • Effects of nicotine on the nucleus accumbens and similarity to those of addictive drugs [19].
  • We now show that enkephalin and catecholamines are released together from primary cultures of bovine adrenal medullary chromaffin cells by nicotine in a Ca2+-dependent manner [20].
  • Nicotine increased endothelial-cell growth and tube formation in vitro, and accelerated fibrovascular growth in vivo [21].

Associations of nicotine with other chemical compounds


Gene context of nicotine


Analytical, diagnostic and therapeutic context of nicotine


  1. The effect of nicotine on energy expenditure during light physical activity. Perkins, K.A., Epstein, L.H., Marks, B.L., Stiller, R.L., Jacob, R.G. N. Engl. J. Med. (1989) [Pubmed]
  2. Transdermal nicotine for active ulcerative colitis. Pullan, R.D., Rhodes, J., Ganesh, S., Mani, V., Morris, J.S., Williams, G.T., Newcombe, R.G., Russell, M.A., Feyerabend, C., Thomas, G.A. N. Engl. J. Med. (1994) [Pubmed]
  3. The safety of transdermal nicotine as an aid to smoking cessation in patients with cardiac disease. Joseph, A.M., Norman, S.M., Ferry, L.H., Prochazka, A.V., Westman, E.C., Steele, B.G., Sherman, S.E., Cleveland, M., Antonnucio, D.O., Hartman, N., McGovern, P.G. N. Engl. J. Med. (1996) [Pubmed]
  4. New treatments for smoking cessation. Hughes, J.R. CA: a cancer journal for clinicians. (2000) [Pubmed]
  5. Pharmacotherapy for nicotine dependence. Henningfield, J.E., Fant, R.V., Buchhalter, A.R., Stitzer, M.L. CA: a cancer journal for clinicians. (2005) [Pubmed]
  6. Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors. Brejc, K., van Dijk, W.J., Klaassen, R.V., Schuurmans, M., van Der Oost, J., Smit, A.B., Sixma, T.K. Nature (2001) [Pubmed]
  7. Personalized medicine and quantitative trait transcripts. Ruden, D.M. Nat. Genet. (2007) [Pubmed]
  8. Nicotine patches for aphthous ulcers due to Behçet's syndrome. Scheid, P., Bohadana, A., Martinet, Y. N. Engl. J. Med. (2000) [Pubmed]
  9. Transdermal nicotine as maintenance therapy for ulcerative colitis. Thomas, G.A., Rhodes, J., Mani, V., Williams, G.T., Newcombe, R.G., Russell, M.A., Feyerabend, C. N. Engl. J. Med. (1995) [Pubmed]
  10. A controlled trial of sustained-release bupropion, a nicotine patch, or both for smoking cessation. Jorenby, D.E., Leischow, S.J., Nides, M.A., Rennard, S.I., Johnston, J.A., Hughes, A.R., Smith, S.S., Muramoto, M.L., Daughton, D.M., Doan, K., Fiore, M.C., Baker, T.B. N. Engl. J. Med. (1999) [Pubmed]
  11. Racial and ethnic differences in serum cotinine levels of cigarette smokers: Third National Health and Nutrition Examination Survey, 1988-1991. Caraballo, R.S., Giovino, G.A., Pechacek, T.F., Mowery, P.D., Richter, P.A., Strauss, W.J., Sharp, D.J., Eriksen, M.P., Pirkle, J.L., Maurer, K.R. JAMA (1998) [Pubmed]
  12. Nicotine, cotinine, and anabasine inhibit aromatase in human trophoblast in vitro. Barbieri, R.L., Gochberg, J., Ryan, K.J. J. Clin. Invest. (1986) [Pubmed]
  13. Nicotine effects on prostaglandin-dependent gastric slow wave rhythmicity and antral motility in nonsmokers and smokers. Kohagen, K.R., Kim, M.S., McDonnell, W.M., Chey, W.D., Owyang, C., Hasler, W.L. Gastroenterology (1996) [Pubmed]
  14. Naloxone challenge in smokers. Preliminary evidence of an opioid component in nicotine dependence. Krishnan-Sarin, S., Rosen, M.I., O'Malley, S.S. Arch. Gen. Psychiatry (1999) [Pubmed]
  15. Abnormal avoidance learning in mice lacking functional high-affinity nicotine receptor in the brain. Picciotto, M.R., Zoli, M., Léna, C., Bessis, A., Lallemand, Y., Le Novère, N., Vincent, P., Pich, E.M., Brûlet, P., Changeux, J.P. Nature (1995) [Pubmed]
  16. Hippocampal synaptic transmission enhanced by low concentrations of nicotine. Gray, R., Rajan, A.S., Radcliffe, K.A., Yakehiro, M., Dani, J.A. Nature (1996) [Pubmed]
  17. Neurobiology: memories of nicotine. McGehee, D.S., Role, L.W. Nature (1996) [Pubmed]
  18. Changes in bronchial epithelium in relation to cigarette smoking, 1955-1960 vs. 1970-1977. Auerbach, O., Hammond, E.C., Garfinkel, L. N. Engl. J. Med. (1979) [Pubmed]
  19. Effects of nicotine on the nucleus accumbens and similarity to those of addictive drugs. Pontieri, F.E., Tanda, G., Orzi, F., Di Chiara, G. Nature (1996) [Pubmed]
  20. Co-release of enkephalin and catecholamines from cultured adrenal chromaffin cells. Livett, B.G., Dean, D.M., Whelan, L.G., Udenfriend, S., Rossier, J. Nature (1981) [Pubmed]
  21. Nicotine stimulates angiogenesis and promotes tumor growth and atherosclerosis. Heeschen, C., Jang, J.J., Weis, M., Pathak, A., Kaji, S., Hu, R.S., Tsao, P.S., Johnson, F.L., Cooke, J.P. Nat. Med. (2001) [Pubmed]
  22. Exposure of the fetus, neonate, and nursed infant to nicotine and cotinine from maternal smoking. Luck, W., Nau, H. N. Engl. J. Med. (1984) [Pubmed]
  23. Functional acetylcholine receptor in PC12 cells reacts with a monoclonal antibody to brain nicotinic receptors. Whiting, P.J., Schoepfer, R., Swanson, L.W., Simmons, D.M., Lindstrom, J.M. Nature (1987) [Pubmed]
  24. Neurotransmitters in the mammalian circadian system. Rusak, B., Bina, K.G. Annu. Rev. Neurosci. (1990) [Pubmed]
  25. Inhibition of catecholamine release by tolbutamide and other sulfonylureas. Hsu, C.Y., Brooker, G., Peach, M.J., Westfall, T.C. Science (1975) [Pubmed]
  26. Nicotine induces cell proliferation by beta-arrestin-mediated activation of Src and Rb-Raf-1 pathways. Dasgupta, P., Rastogi, S., Pillai, S., Ordonez-Ercan, D., Morris, M., Haura, E., Chellappan, S. J. Clin. Invest. (2006) [Pubmed]
  27. Sex-specific expression of gastrin-releasing peptide receptor: relationship to smoking history and risk of lung cancer. Shriver, S.P., Bourdeau, H.A., Gubish, C.T., Tirpak, D.L., Davis, A.L., Luketich, J.D., Siegfried, J.M. J. Natl. Cancer Inst. (2000) [Pubmed]
  28. Corticotropin-releasing factor-binding protein ligand inhibitor blunts excessive weight gain in genetically obese Zucker rats and rats during nicotine withdrawal. Heinrichs, S.C., Lapsansky, J., Behan, D.P., Chan, R.K., Sawchenko, P.E., Lorang, M., Ling, N., Vale, W.W., De Souza, E.B. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  29. A common haplotype of the nicotine acetylcholine receptor alpha 4 subunit gene is associated with vulnerability to nicotine addiction in men. Feng, Y., Niu, T., Xing, H., Xu, X., Chen, C., Peng, S., Wang, L., Laird, N., Xu, X. Am. J. Hum. Genet. (2004) [Pubmed]
  30. Nicotine and smokeless tobacco. Benowitz, N.L. CA: a cancer journal for clinicians. (1988) [Pubmed]
  31. Nicotine activates and desensitizes midbrain dopamine neurons. Pidoplichko, V.I., DeBiasi, M., Williams, J.T., Dani, J.A. Nature (1997) [Pubmed]
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