Contribution of CNS nicotine metabolites to the neuropharmacological effects of nicotine and tobacco smoking

Biochemical Pharmacology

Volumn 54, Issue 7, 1997, Pages 743-753

  Crooks, Peter A ^a   Dwoskin, Linda P ^a  

^a University of Kentucky   (United States)

Author keywords

Behavioral and neurochemical assays; CNS metabolism; Cotinine; Dopamine; Nicotine; Nicotinic receptor; Norcotinine; Nornicotine

Indexed keywords

COTININE; NICOTINE; NICOTINIC RECEPTOR; NORNICOTINE; RECEPTOR SUBTYPE;

CIGARETTE SMOKING; DOPAMINERGIC SYSTEM; DRUG METABOLISM; HUMAN; NEUROTOXICITY; PRIORITY JOURNAL; REVIEW;

EID: 0030805422     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00117-2     Document Type: Note

References (183)

1. Surgeon General's Report, Tobacco use and drug dependency. In: Nicotine Addiction: The Health Consequences of Smoking, Report of the Surgeon General, pp. 145-239. U.S. Public Health Service, Rockville, MD, 1988.
2. Clarke PBS, Nicotine and smoking: A perspective from animal studies. Psychopharmacology 92: 135-143, 1987.
3. Pomerleau CS and Pomerleau OF, Euphoriant effects of nicotine in smokers. Psychopharmacology 108: 460-465, 1992.
4. Damaj MI, Welch SP and Martin BR, In vivo pharmacological effects of dihydro-Β-erythroidine, a nicotinic antagonist, in mice. Psychopharmacology 117: 67-73, 1995.
5. Stolerman IP, Garcha HS, Pratt JA and Kumar R, Role of training dose in discrimination of nicotine and related compounds by rats. Psychopharmacology 84: 413-419, 1984.
6. Stolerman IP, Goldfarb T, Fink R and Jarvik ME, Influencing cigarette smoking with nicotine antagonists. Psychopharmacology 28: 247-259, 1973.
7. Henningfield JE and Goldberg SR, Nicotine as a reinforcer in human subjects and laboratory animals. Pharmacol Biochem Behav 19: 989-992, 1983.
8. Rose JE, Behm FM, Westman EC, Levin ED, Stein RM, Lane JD and Ripka GV, Combined effects of nicotine and mecamylamine in attenuating smoking satisfaction. Exp Clin Psychopharmacol 2: 328-344, 1994.
9. Lingle C, Blockade of cholinergic channels by chlorisondamine on a crustacean muscle. J Physiol (Lond) 339: 395-417, 1983.
10. Varanda WA, Aracava Y, Sherby SM, Van Meter WG, Eldefrawi ME and Albuquerque EX, The acetylcholine receptor of the neuromuscular junction recognizes mecamylamine as a noncompetitive antagonist. Mol Pharmacol 28: 128-137, 1985.
11. 3H]Mecamylamine binding to rat brain membranes. Biochem Pharmacol 40: 2105-2110, 1990.
12. Martin TJ, Suchocki J, May EL and Martin BR, Pharmacological evaluation of the antagonism of nicotine's central effects by mecamylamine and pempidine. J Pharmacol Exp Ther 254: 45-51, 1990.
13. 3H]( - )-nicotine binding in rat cortex. Neuropharmacology 32: 847-853, 1993.
14. Peng O, Gerzanich V, Anand R, Whiting PJ and Lindstrom J, Nicotine-induced increase in the neuronal nicotinic receptors results from a decrease in the rate of receptor turnover. Mol Pharmacol 46: 523-530, 1994.
15. O'Dell TJ and Christensen BN, Mecamylamine is a selective non-competitive antagonist of N-methyl-D-aspartate and aspartate-induced currents in horizontal cells dissociated from the catfish retina. Neurosci Lett 94: 93-98, 1988.
16. 3H]MK801 binding to the N-methyl-D-aspartate receptor reveals drug interactions with the zinc and magnesium binding sites. J Pharmacol Exp Ther 247: 1025-1031, 1988.
17. 3H-[1-(2-thienyl)cyclohexyl]-piperidine) binding in rat hippocampus. Synapse 3: 129-135, 1989.
18. 3H]MK-801 to brain membranes, but not via the stimulation of high-affinity nicotinic receptors. Brain Res 524: 319-321, 1990.
19. 3H]( - )nicotine to rat brain membranes and its inhibition by analogues of nicotine. Neuropharmacology 27: 235-241, 1988.
20. 3H]dopamine release from synaptosomes prepared from mouse striatum. J Neurochem 59: 848-856, 1992.
21. Vidal C and Changeux JP, Pharmacological profile of nicotinic acetylcholine receptors in rat pre-frontal cortex: An electrophysiological study in a slice preparation. Neuroscience 29: 261-270, 1989.
22. Alkondon M and Albuquerque EX, Initial characterization of the nicotinic acetylcholine receptors in rat hippocampal neurons. J Recept Res 11: 1001-1021, 1991.
23. Mulle C, Vidal C, Benoit P and Changeux J-P, Existence of different subtypes of nicotinic acetylcholine receptors in the rat habenulo-interpeduncular system. J Neurosci 11: 2588-2597, 1991.
24. Gorrod JW and Jenner PJ, The metabolism of tobacco alkaloids. Essays Toxicol 6: 35-78, 1975.
25. Kyerematen GA and Vesell ES, Metabolism of nicotine. Drug Metab Rev 23: 3-41, 1991.
26. Gorrod JW and Wahren J (Eds.), Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion. Chapman & Hall, London, 1993.
27. Whiting PJ and Lindstrom JM, Characterization of bovine and human neuronal nicotinic acetylcholine receptors using monoclonal antibodies. J Neurosci 8: 3395-3404, 1988.
28. Patrick J, Boulter J, Deneris E, Wada K, Wada E, Connolly L, Swanson L and Heinemann S, Structure and function of neuronal nicotinic acetylcholine receptors deduced from cDNA clones. Prog Brain Res 79: 27-33, 1988.
29. Deneris ES, Connolly J, Rogers SW and Duvoisin R, Pharmacological and functional diversity of neuronal nicotinic acetylcholine receptors. Trends Pharmacol Sci 12: 34-40, 1991.
30. Karlin A, Structure of nicotinic acetylcholine receptors. Curr Opin Neurobiol 3: 299-309, 1993.
31. Le Novère NL and Changeux J-P, Molecular evolution of the nicotinic acetylcholine receptor: An example of multi-gene family in excitable cells. J Mol Evol 40: 155-172, 1995.
32. Luetje CW, Patrick J and Séguéla P, Nicotine receptors in the mammalian brain. FASEB J 4: 2753-2760, 1990.
33. Role LW, Diversity in primary structure and function of neuronal nicotinic acetylcholine receptor channels. Curr Opin Neurobiol 2: 254-262, 1992.
34. Sargent PB, The diversity of neuronal nicotinic acetylcholine receptors. Annu Rev Neurosci 16: 403-443, 1993.
35. McGehee DS and Role LW, Physiological diversity of nicotinic acetylcholine receptors expressed by vertebrate neurons. Annu Rev Physiol 57: 521-526, 1995.
36. Cachelin AB and Rust G, Β-Subunits co-determine the sensitivity of rat neuronal nicotinic receptors to antagonists. Pflügers Arch 429: 449-451, 1995.
37. Morris BJ, Hicks AA, Wisden W, Darlison MG, Hunt SP and Barnard EA, Distinct regional expression of nicotinic acetylcholine receptor genes in chick brain. Mol Brain Res 7: 305-315, 1990.
38. Anand R, Conroy WG, Schoepfer R, Whiting P and Lindstrom J, Neuronal nicotinic acetylcholine receptors expressed in Xenopus have a pentameric quaternary structure. J Biol Chem 17: 11192-11198, 1991.
39. Cooper E, Couturier S and Ballivet M, Pentameric structure and subunit stoichiometry of a neuronal nicotinic acetylcholine receptor. Nature 350: 235-238, 1991.
40. Conroy WG, Vernallis AB and Berg DK, The α5 gene product assembles with multiple acetylcholine receptor subunits to form distinctive receptor subtypes in brain. Neuron 9: 679-691, 1992.
41. Vernallis AB, Conroy WG and Berg DK, Neurons assemble acetylcholine receptors with as many as three kinds of subunits while maintaining subunit segregation among receptor subtypes. Neuron 10: 451-464, 1993.
42. ++ regulatory site. Soc Neurosci Abstr 21: 1333, 1995.
43. Forsayeth JR, Kobrin E, Winegar BD and Fitzgerald DJ, The nicotinic acetylcholine receptor in cerebellum is composed of four different subunits. Soc Neurosci Abstr 21: 1583, 1995.
44. Luetje CW and Patrick J, Both α- and Β-subunits contribute to the agonist sensitivity of neuronal nicotinic acetylcholine receptors. J Neurosci 11: 837-845, 1991.
45. Luetje CW, Wada K, Rogers S, Abramson SN, Tsuji K, Heinemann S and Patrick J, Neurotoxins distinguish between different neuronal nicotinic acetylcholine receptor subunit combinations. J Neurochem 55: 632-640, 1990.
46. Luetje CW, Piattoni M and Patrick J, Mapping of ligand binding sites of neuronal nicotinic acetylcholine receptors using chimeric α subunits. Mol Pharmacol 44: 657-666, 1993.
47. Amar M, Thomas P, Johnson C, Lunt GG and Wonnacott S, Agonist pharmacology of the neuronal α7 nicotinic receptor expressed in Xenopus oocytes. FEBS Lett 327: 284-288, 1993.
48. Decker MW, Brioni JD, Bannon AW and Arneric SP, Diversity of neuronal nicotinic acetylcholine receptors: Lessons from behavior and implications for CNS therapeutics. Life Sci 56: 545-570, 1995.
49. Stolerman IP and Jarvis MJ, The scientific case that nicotine is addictive. Psychopharmacology 117: 2-10, 1995.
50. Goldberg SR, Spealman RD and Goldberg DM, Persistent behavior at high rates maintained by intravenous self-administration of nicotine. Science 214: 573-575, 1981.
51. Cox BM, Goldstein A and Nelson WT, Nicotine self-administration in rats. Br J Pharmacol 83: 49-55, 1984.
52. Corrigall WA, Franklin KBJ, Coen KM and Clarke PBS, The mesolimbic dopaminergic system is implicated in the reinforcing effects of nicotine. Psychopharmacology 107: 285-289, 1992.
53. 3 antagonists ICS 205-930 and MDL 72222. Pharmacol Biochem Behav 49: 67-71, 1994.
54. Sannerud CA, Prada J, Goldberg DM and Goldberg SR, The effects of sertraline on nicotine self-administration and food-maintained responding in squirrel monkeys. Eur J Pharmacol 271: 461-469, 1994.
55. Donny EC, Caggiula AR, Knof S and Brown C, Nicotine self-administration in rats. Psychopharmacology 122: 390-394, 1995.
56. Fudala PJ, Teoh KW and Iwamoto ET, Pharmacologic characterization of nicotine-induced conditioned place preference. Pharmacol Biochem Behav 22: 237-241, 1985.
57. Shoaib M, Stolerman IP and Kumar RC, Nicotine-induced place preferences following prior nicotine exposure in rats. Psychopharmacology 113: 445-452, 1994.
58. Risinger FO and Oakes RA, Nicotine-induced conditioned place preference and conditioned place aversion in mice. Pharmacol Biochem Behav 51: 457-461, 1995.
59. Corrigall WA and Coen KM, Nicotine maintains robust self-administration in rats on a limited access schedule. Psychopharmacology 99: 473-478, 1989.
60. Dworkin SE, Vrana SL, Broadbent J and Robinson JH, Comparing the reinforcing effects of nicotine, caffeine, methylphenidate and cocaine. Med Chem Res 2: 593-602, 1993.
61. Meltzer LT and Rosecrans JA, Investigations on the CNS sites of action of the discriminative stimulus effects of arecoline and nicotine. Pharmacol Biochem Behav 15: 21-26, 1981.
62. Clarke PBS and Kumar R, Characterization of the locomotor stimulant action of nicotine in tolerant rats. Br J Pharmacol 80: 587-594, 1983.
63. Clarke PBS and Kumar R, The effect of nicotine on locomotor activity in non-tolerant and tolerant rats. Br J Pharmacol 78: 329-337, 1983.
64. Clarke PBS, Dopaminergic mechanisms in the locomotor stimulant effects of nicotine. Biochem Pharmacol 40: 1427-1432, 1990.
65. Stolerman IP, Fink R and Jarvik ME, Acute and chronic tolerance to nicotine measured by activity in rats. Psychopharmacology 30: 329-342, 1973.
66. Stolerman IP, Bunker P and Jarvik ME, Nicotine tolerance in rats; role of dose and dose interval. Psychopharmacology 34: 317-324, 1974.
67. Collins AC, Romm E and Wehner JM, Nicotine tolerance: An analysis of the time course of its development and loss in the rat. Psychopharmacology 96: 7-14, 1988.
68. Collins AC, Romm E and Wehner JM, Dissociation of the apparent relationship between nicotine tolerance and upregulation of nicotinic receptors. Brain Res Bull 25: 373-379, 1990.
69. 3H]acetylcholine to nicotinic receptors. Neuropharmacology 24: 527-531, 1985.
70. Ksir C, Hakan RL and Kellar KJ, Chronic nicotine and locomotor activity: Influences of exposure dose and test dose. Psychopharmacology 92: 25-29, 1987.
71. Clarke PBS, Fu DS, Jakubovic A and Fibiger HC, Evidence that mesolimbic dopaminergic activation underlies the locomotor stimulant action of nicotine in rats. J Pharmacol Exp Ther 246: 701-708, 1988.
72. Fung YK and Lau Y-S, Receptor mechanisms of nicotine-induced locomotor hyperactivicy in chronic nicotine-treated rats. Eur J Pharmacol 152: 263-271, 1988.
73. Benwell MEM and Balfour DJK, The effects of acute and repeated nicotine treatment on nucleus accumbens dopamine and locomotor activity. Br J Pharmacol 105: 849-856, 1992.
74. Ksir C, Acute and chronic nicotine effects on measures of activity in rats: A multivariate analysis. Psychopharmacology 115: 105-109, 1994.
75. Stolerman IP, Garcha HS and Mirza NR, Dissociations between the locomotor stimulant and depressant effects of nicotinic agonists in rats. Psychopharmacology 117: 430-437, 1995.
76. Fibiger HC and Phillips AG, Role of catecholamine transmitters in brain reward systems: Implications for the neurobiology of affect. In: Brain Reward Systems and Abuse (Eds. Engel J and Oreland L), pp. 61-74. Raven Press, New York, 1987.
77. Balfour DJK and Benwell MEM, The role of brain dopamine systems in the psychopharmacological responses to nicotine. Asia Pac J Pharmacol 8: 153-167, 1993.
78. Simon H, Scatton B and LeMoal M, Dopaminergic A10 neurones are involved in cognitive functions. Nature 285: 150-151, 1980.
79. Roberts DCS and Koob GF, Disruption of cocaine self-administration following 6-hydroxydopamine lesions of the ventral tegmental area in rats. Pharmacol Biochem Behav 17: 901-904, 1983.
80. Wise RA and Bozarth MA, A psychomotor stimulant theory of addiction. Psychol Rev 94: 469-492, 1987.
81. Self DW and Nestler EJ, Molecular mechanisms of drug reinforcement and addiction. Annu Rev Neurosci 18: 463-495, 1995.
82. Grenhoff J, Aston-Jones G and Svensson TH, Nicotinic effects on the firing pattern of midbrain dopamine neurons. Acta Physiol Scand 128: 351-358, 1986.
83. 3H]acetylcholine on catecholamine and serotonin axons in brain. J Neurochem 42: 1495-1498, 1984.
84. Clarke PBS and Pert A, Autoradiographic evidence for nicotine receptors on nigrostriatal and mesolimbic dopaminergic neurons. Brain Res 348: 355-385, 1985.
85. Calabresi P, Lacey MG and North RA, Nicotinic excitation of rat ventral tegmental neurons in vitro studied by intracellular recording. Br J Pharmacol 98: 135-140, 1989.
86. Fuxe K, Andersson K, Hartstrand A and Agnati LF, Increases in dopamine utilization in certain limbic dopaminergic terminal populations after a short period of intermittent exposure of male rats to cigarette smoke. J Neural Transm 67: 15-29, 1986.
87. Lapin EP, Maker HS, Sershen H and Lajtha A, Action of nicotine on accumbens dopamine and attenuation with repeated administration. Eur J Pharmacol 160: 53-59, 1989.
88. 3H] dopamine release by nicotine in rat nucleus accumbens. J Neurochem 49: 1449-1454, 1987.
89. 3H]tyrosine in rat nucleus accumbens. J Pharm Pharmacol 41: 66-68, 1989.
90. Imperato A, Mulas A and DiChiara G, Nicotine preferentially stimulates dopamine release in the limbic system of freely moving rats. Eur J Pharmacol 132: 337-338, 1986.
91. Damsma G, Day J and Fibiger HC, Lack of tolerance to nicotine-induced dopamine release in the nucleus accumbens. Eur J Pharmacol 168: 563-368, 1989.
92. Brazell MP, Mitchell SN, Joseph MH and Gray JA, Acute administration of nicotine increases the in vivo extracellular levels of dopamine, 3,4-dihydroxyphenylacetic acid and ascorbic acid preferentially in the nucleus accumbens of the rat: Comparison with the caudate-putamen. Neuropharmacology 29: 1177-1185, 1990.
93. Toth E, Sershen H, Hashim A, Vizi ES and Lajtha A, Effect of nicotine on extracellular levels of neurotransmitters assessed by microdialysis in various brain regions: Role of glutamic acid. Neurochem Res 17: 265-271, 1992.
94. Benwell MEM, Balfour DJK and Lucchi HM, Influence of tetrodotoxin and calcium on changes in extracellular dopamine levels evoked by systemic nicotine. Psychopharmacology 112: 467-474, 1993.
95. Benwell MEM, Balfour DJK and Birrell CE, Desensitization of the nicotine-induced mesolimbic dopamine responses during constant infusion with nicotine. Br J Pharmacol 114: 454-460, 1995.
96. Nisell M, Nomikos GG and Svensson TH, Systemic nicotine-induced dopamine release in the rat nucleus accumbens is regulated by nicotinic receptors in the ventral tegmental area. Synapse 16: 36-44, 1994.
97. Nisell M, Nomikos GG and Svensson TH, Infusion of nicotine in the ventral tegmental area or the nucleus accumbens of the rat differentially affects accumbal dopamine release. Pharmacol Toxicol 75: 348-352, 1994.
98. Singer G, Wallace M and Hall R, Effects of dopaminergic nucleus accumbens lesions on the acquisition of schedule-induced self-injection of nicotine in the rat. Pharmacol Biochem Behav 17: 579-581, 1982.
99. Lichtensteiger W, Hefti F, Felix D, Huwyler S, Melamed E and Schlumpf M, Stimulation of nigrostriatal dopamine neurons by nicotine. Neuropharmacology 21: 963-968, 1982.
100. Clarke PBS, Hommer DW, Pert A and Skirboll LR, Electrophysiological actions of nicotine on substantia nigra single units. Br J Pharmacol 85: 827-835, 1985.
101. Giorguieff-Chesselet MR, Kennel ML, Wandscheer D and Glowinski J, Regulation of dopamine release by presynaptic nicotinic receptors in rat striatal slices: Effect of nicotine in a low concentration. Life Sci 25: 1257-1262, 1979.
102. Arqueros L, Naquira D and Zunino E, Nicotine-induced release of catecholamines from rat hippocampus and striatum. Biochem Pharmacol 27: 2667-2674, 1978.
103. 14C]dopamine in rat brain striatum and hypothalamus slices. Neuropharmacology 13: 1025-1032, 1974.
104. Westfall TC, Grant H and Perry H, Release of dopamine and 5-hydroxytryptamine from rat striatal slices following activation of nicotinic cholinergic receptors. Gen Pharmacol 14: 321-325, 1983.
105. Westfall TC, Mereu G, Vickery L, Perry H, Naes L and Yoon KP, Regulation by nicotine of midbrain dopamine neurons. Prog Brain Res 79: 173-185, 1989.
106. 3H]dopamine release in rat striatum. J Neurochem 56: 603-610, 1991.
107. Harsing LG, Sershen H and Lajtha A, Dopamine efflux from striatum after chronic nicotine: Evidence for autoreceptor desensitization. J. Neurochem 59: 48-54, 1992.
108. Schulz DW, Kuchel GA and Zigmond RE, Decline in response to nicotine in aged rat striatum: Correlation with a decrease in a subpopulation of nicotinic receptors. J Neurochem 61: 2225-2232, 1993.
109. Sacaan AI, Dunlop JL and Lloyd KG, Pharmacological characterization of a neuronal acetylcholine-gated ion channel receptor-mediated hippocampal norepinephrine and striatal dopamine release from rat brain slices. J Pharmacol Exp Ther 274: 224-230, 1995.
110. + stimulation, methamphetamine and nicotinic drugs. Brain Res 279: 330-334, 1983.
111. Chesselet MF, Presynaptic regulation of neurotransmitter release in the brain: Facts and hypotheses. Neuroscience 12: 347-375, 1984.
112. Rapier C, Lunt GG and Wonnacott S, Stereoselective nicotine-induced release of dopamine from striatal synaptosomes: Concentration dependence and repetitive stimulation. J Neurochem 50: 1123-1130, 1988.
113. 3H]dopamine release from striatal synaptosomes: Pharmacological characterization. J Neurochem 54: 937-945, 1990.
114. El-Bizri H and Clarke PBS, Blockade of nicotinic receptor-mediated release of dopamine from striatal synaptosomes by chlorisondamine and other nicotinic antagonists administered in vitro. Br J Pharmacol 111: 406-413, 1994.
115. 3H]DA release from mouse striatal synaptosomes. J Neurochem 62: 1390-1398, 1994.
116. Rowell PP and Hillebrand JA, Desensitization of nicotine-stimulated dopamine release from rat striatal synaptosomes. Pharmacologist 34: 154, 1992.
117. Rowell PP and Hillebrand JA, Characterization of nicotine-induced desensitization of evoked dopamine release from rat striatal synaptosomes. J Neurochem 63: 561-569, 1994.
118. 3H]dopamine from rat striatal synaptosomes. Neurosci Lett 189: 171-175, 1995.
119. Bhat RV, Marks MJ and Collins AC, Effects of chronic nicotine infusion on kinetics of high-affinity nicotine binding. J Neurochem 62: 574-581, 1994.
120. Russell MA, Jarvis M, Iyer R and Feyerbend C, Relation of nicotine yield in cigarettes to blood nicotine concentrations in smokers. Br Med J 280: 972-976, 1980.
121. Kogen NJ, Verebey K, Jaffee JH and Mule SJ, Simultaneous determination of nicotine and cotinine in human plasma by nitrogen detection gas liquid chromatography. J Forensic Sci 26: 6-11, 1981.
122. Westfall TC, Perry H and Vicery L, Mechanisms of nicotine regulation of dopamine release in neostriatum. In: Tobacco Smoking and Nicotine (Eds. Martin WR, VanLoon GR, Iwamoto ET and Davis L), pp. 209-223. Plenum, New York, 1987.
123. Izenwasser S and Cox BM, Inhibition of dopamine uptake by cocaine and nicotine: Tolerance to chronic treatments. Brain Res 573: 119-125, 1992.
124. Kramer HK, Sershen H, Lajtha A and Reith MEA, The effect of nicotine on catecholaminergic storage vesicles. Brain Res 503: 296-296, 1989.
125. Carr LA, Rowell PP and Pierce WM, Effects of subchronic nicotine administration on central dopaminergic mechanisms in the rat. Neurochem Res 14: 511-515, 1989.
126. Rowell PP and Hill AS, Apparent inability of nicotine to inhibit dopamine uptake into rat striatal tissue in vitro. Pharmacologist 35: 134, 1993.
127. Hart C and Ksir C, Nicotine effects on dopamine clearance in rat nucleus accumbens. J Neurochem 66: 216-221, 1996.
128. Harsing LG, Sershen H, Vizi SE and Lajtha A, N-Type calcium channels are involved in the dopamine releasing effect of nicotine. Neurochem Res 17: 729-734, 1992.
129. Marks MJ, Grady SR and Collins AC, Downregulation of nicotinic receptor function after chronic nicotine infusion. J Pharmacol Exp Ther 266: 1268-1276, 1993.
130. Yu ZJ and Wecker L, Chronic nicotine administration differentially affects neurotransmitter release from rat striatal slices. J Neurochem 63: 186-194, 1994.
131. Marks MJ, Burch JB and Collins AC, Effects of chronic nicotine infusion on tolerance development and nicotinic receptors. J Pharmacol Exp Ther 226: 817-825, 1983.
132. Schwartz RD and Kellar KJ, Nicotinic cholinergic receptor binding sites in the brain: Regulation in vivo. Science 220: 214-216, 1983.
133. 3H]( - )nicotine label the same recognition site in rat brain. Mol Pharmacol 31: 169-174, 1987.
134. Nordberg A, Romanelli L, Sundwall A, Bianchi C and Beani L, Effects of acute and subchronic nicotine treatment on cortical acetylcholine release and on nicotinic receptors in rats and guinea-pigs. Br J Pharmacol 98: 71-78, 1989.
135. Bhat RV, Turner SL, Selvaag SR, Marks MJ and Collins AC, Regulation of brain nicotinic receptors by chronic agonist infusion. J Neurochem 56: 1932-1939, 1991.
136. Sanderson EM, Drasdo AL, McCrea K and Wonnacott S, Upregulation of nicotinic receptors following continuous infusion of nicotine is brain-region-specific. Bruin Res 617: 349-352, 1993.
137. Zhang X, Gong Z-H and Nordberg A, Effects of chronic treatment with ( + )- and ( - )-nicotine on nicotinic acetylcholine receptors and N-methyl-D-aspartate receptors in rat brain. Brain Res 644: 32-39, 1994.
138. 3H]nicotine to a single class of high affinity sites in rat brain membranes. Mol Pharmacol 29: 448-454, 1986.
139. Bencherif M, Fowler K, Lukas RJ and Lippiello PM, Mechanisms of up-regulation of neuronal nicotinic acetylcholine receptors in clonal cell lines and primary cultures of fetal rat brain. J Pharmacol Exp Ther 275: 987-994, 1995.
140. 3H] nicotine binding sites in human brain. J Neurochem 50: 1243-1247, 1988.
141. Collins AC, Luo Y, Selvaag S and Marks MJ, Sensitivity to nicotine and brain nicotinic receptors are altered by chronic nicotine and mecamylamine infusion. J Pharmacol Exp Ther 271: 125-133, 1994.
142. Whiting P, Schoepfer R, Lindstrom J and Priestley T, Structural and pharmacological characterization of the major brain nicotinic acetylcholine receptor subtype stably expressed in mouse fibroblasts. Mol Pharmacol 40: 463-472, 1991.
143. Flores CM, Rogers SW, Pabreza LA, Wolfe BB and Kellar KJ, A subtype of nicotinic cholinergic receptor in rat brain is composed of α4 and Β2 subunits and is up-regulated by chronic nicotine treatment. Mol Pharmacol 41: 31-37, 1992.
144. Schulz DW and Zigmond RE, Neuronal bungarotoxin blocks the nicotinic stimulation of dopamine release from rat striatum. Neurosci Lett 98: 310-316, 1989.
145. Crooks PA, N-Oxidation, N-methylation and N-conjugation reactions of nicotine. In: Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion (Eds. Gorrod JW and Wahren J), pp. 81-109. Chapman & Hall, London, 1993.
146. Nwosu CG and Crooks PA, Species variation and stereoselectivity in the metabolism of nicotine enantiomers. Xenobiotica 18: 1361-1372, 1988.
147. Kyerematen GA, Morgan M, Chattopadhyay B, deBethizy JD and Vesell ES, Disposition of nicotine and eight metabolites in smokers and nonsmokers: Identification in smokers of two metabolites that are longer lived than cotinine. Clin Pharmacol Ther 48: 641-651, 1990.
148. McKennis H Jr, Turnbull LB, Bowman ER and Wada E, Demethylation of cotinine in vivo. J Am Chem Soc 81: 3951-3954, 1959.
149. McKennis H, Turnbull LB and Schwartz SL, Demethylation in the metabolism of ( - )-nicotine. J Biol Chem 237: 541-545, 1962.
150. Dagne E and Castagnioli N, Cotinine-N-oxide, a new metabolite of nicotine. J Med Chem 15: 840-841, 1972.
151. Bowman ER, Turnbull LB and McKennis H, Metabolism of nicotine in the human and excretion of pyridine compounds in smokers. J Pharmacol Exp Ther 127: 91-102, 1959.
152. Bowman ER and McKennis H, Studies on the metabolism of ( - )cotinine in the human. J Pharmacol Exp Ther 135: 306-311, 1962.
153. Curvall M and Kazeni Vala E, Nicotine and metabolites: Analysis and levels in body fluids. In: Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion (Eds. Gorrod JW and Wahren J), pp. 147-179. Chapman & Hall, London, 1993.
154. Gabrielsson J and Gumbleton M, Kinetics of nicotine and its metabolites in animals. In: Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion (Eds. Gorrod JW and Wahren J), pp. 181-195. Chapman & Hall, London, 1993.
155. Neurath GB, Nicotine metabolism beyond cotinine. In: Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion (Eds. Gorrod JW and Wahren J), pp. 61-80. Chapman & Hall, London, 1993.
156. Aislaitner G, Li Y and Gorrod JW, In vitro studies on ( - )-( S )-nornicotine. Med Sci Res 20: 897-899, 1992.
157. Cundy KC and Crooks PA, High performance liquid chromatographic method for the determination of N-methylated metabolites of nicotine. J Chromatogr B Biomed Appl 306: 291-301, 1984.
158. Plowchalk DR, Andersen ME and deBethizy JD, A physiologically based pharmacokinetic model for nicotine disposition in the Sprague-Dawley rat. Toxicol Appl Pharmacol 116: 177-188, 1992.
159. 11C]nicotine and its regional distribution in the mouse brain: A potential tracer for visualization of brain nicotinic receptors by positron emission tomography. Chem Pharm Bull 40: 734-736, 1992.
160. Stalhandske T, Effects of increased liver metabolism of nicotine on its uptake, elimination and toxicity in mice. Acta Physiol Scand 80: 222-234, 1970.
161. Petersen DR, Norris KJ and Thompson JA, A comparative study of the disposition of nicotine and its metabolites in three inbred strains of mice. Drug Metab Dispos 12: 725-731, 1984.
162. Deutsch J, Hegedus L, Greig NH, Rapoport SI and Soncrant TT, Electron-impact and chemical ionization detection of nicotine and cotinine by gas chromatography-mass spectrometry in rat plasma and brain. J Chromatogr 579: 93-98, 1992.
163. Risner ME, Goldberg SR, Prada JA and Cone EJ, Effects of nicotine, cocaine and some of their metabolites on schedule controlled responding by beagle dogs and squirrel monkeys. J Pharmacol Exp Ther 234: 113-119, 1985.
164. Risner ME, Cone EJ, Benowitz NL and Jacob PJ, Effects of stereoisomers of nicotine and nornicotine on schedule controlled responding and physiological parameters of dogs. J Pharmacol Exp Ther 244: 807-813, 1988.
165. Goldberg SR, Risner ME, Stolerman IP, Reaville C and Garcha HS, Nicotine and some related compounds: Effects on schedule controlled behavior and discriminative properties in rats. Psychopharmacology 97: 295-302, 1989.
166. Dwoskin LP, Buxton ST, Jewell AL and Crooks PA, S( - ) Nornicotine increases dopamine release in a calcium-dependent manner from superfused rat striatal slices. J Neurochem 60: 2167-2174, 1993.
167. 3H]nicotine binding in rat whole brain. NIDA Res Monogr 162: 311, 1995.
168. 3H] dopamine. J Pharmacol Exp Ther, in press.
169. Crooks PA, Li M and Dwoskin LP, Determination of nicotine metabolites in rat brain after peripheral radiolabeled nicotine administration: Detection of nornicotine. Drug Metab Dispos 23: 1175-1177, 1995.
170. Crooks PA, Li M and Dwoskin LP, Metabolites of nicotine in rat brain after peripheral nicotine administration: Cotinine, nornicotine and norcotinine. Drug Metab Dis 25: 47-54, 1997.
171. Kisaki T and Tamaki E, Phytochemical studies on tobacco alkaloids. I. Optical rotary power of nornicotine. Arch Biochem Biophys 92: 351-355, 1961.
172. Zhang Y, Jacob P III and Benowitz ND, Determination of nornicotine in smokers' urine by gas chromatography following reductive alkylation to N′-propylnornicotine. J Chromatogr 525: 349-357, 1990.
173. Liu X, Jacob P III and Castaglioni N Jr, The metabolic fate of the minor tobacco alkaloids. In: Nicotine and Related Alkaloids: Absorption, Distribution, Metabolism and Excretion (Eds. Gorrod JW and Wahren J), pp. 129-145. Chapman & Hall, London, 1993.
174. Copeland JR, Adem A, Jacob P III and Nordberg A, A comparison of the binding of nicotine and nornicotine stereoisomers to nicotinic binding sites in rat brain cortex. Naunyn Schmeidebergs Arch Pharmacol 343: 123-127, 1991.
175. 3H] nicotine binding by the enantiomers of nicotine, nornicotine and anatoxin-a in membranes and solubilized preparations of different brain regions of rat. Naunyn Schmiedebergs Arch Pharmacol 348: 28-34, 1993.
176. 3H]dopamine release by pyridino N-substituted nicotine analogues: A new class of nicotinic antagonist. Drug Dev Res 36: 91-102, 1995.
177. Crooks PA, Teng LH, Li M, Bardo MT and Dwoskin LP, Cotinine pharmacology: Brain uptake and metabolism, effects on dopamine release and lack of behavioral sensitization after chronic administration to rats. NIDA Res Monogr, in press.
178. Abood LG, Reynolds DT, Booth H and Bidlack JM, Sites and mechanisms for nicotine's action in the brain. Neurosci Biobehav Rev 5: 479-486, 1981.
179. 3H]nicotine. Neurochem Res 10: 259-267, 1985.
180. DeClercq M and Truhaut R, Recherches sur le metabolisme du tryptophane chez le rat soumis a l'intoxication chronique par la cotinine. Etude de l'elimination urinaire et dosage dans le cerveau et les intestins de certains derives inoliques. Bull Soc Chim Biol (Paris) 45: 995-1001, 1963.
181. Essman WB, Nicotine-related neurochemical changes: Some implications for motivational mechanisms and differences. In: Smoking Behavior: Motives and Incentives (Ed. Dunn WL Jr), pp. 51-65. Winston & Sons, Washington, DC, 1973.
182. Benowitz NL, Kuyt F, Jacob P, Jones P, Jones RT and Osman AL, Cotinine disposition and effects. Clin Pharmacol Ther 34: 604-614, 1983.
183. Keenan RM, Hatsukami DK, Pentel PR, Thompson TN and Grillo ME, Pharmacodynamic effects of cotinine in abstinent cigarette smokers. Clin Pharmacol Ther 55: 581-590, 1994.