(−)-Nicotine

Papers

Effect Of Nicotine And Cigarette Smoke On An Experimental Model Of Intraepithelial Lesions And Pancreatic Adenocarcinoma Induced By 7,12-dimethylbenzanthracene In Mice. Bersch, V.P., et al. Pancreas 38, 65-70, (2009)

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Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 3'-substituted deschloroepibatidine analogues. Novel nicotinic antagonists. F Ivy Carroll et al J. Med. Chem. 48, 1221-8, (2005)

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Novel pyridyl ring C5 substituted analogues of epibatidine and 3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine (A-84543) as highly selective agents for neuronal nicotinic acetylcholine receptors containing beta2 subunits. Zhi-Liang Wei et al J. Med. Chem. 48, 1721-4, (2005)

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5-substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6. Travis T Denton et al J. Med. Chem. 48, 224-39, (2005)

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Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk). Giulia Caron et al J. Med. Chem. 48, 3269-79, (2005)

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Varenicline: an alpha4beta2 nicotinic receptor partial agonist for smoking cessation. Jotham W Coe et al J. Med. Chem. 48, 3474-7, (2005)

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Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. Laura E Korhonen et al J. Med. Chem. 48, 3808-15, (2005)

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Quantitative structure-activity relationship analysis of inhibitors of the nicotine metabolizing CYP2A6 enzyme. Minna Rahnasto et al J. Med. Chem. 48, 440-9, (2005)

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Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations. Anders A Jensen et al J. Med. Chem. 48, 4705-45, (2005)

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2-(Arylmethyl)-3-substituted quinuclidines as selective alpha 7 nicotinic receptor ligands. Anatoly Mazurov et al Bioorg. Med. Chem. Lett. 15, 2073-7, (2005)

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A discriminant model constructed by the support vector machine method for HERG potassium channel inhibitors. Motoi Tobita et al Bioorg. Med. Chem. Lett. 15, 2886-90, (2005)

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In pursuit of alpha4beta2 nicotinic receptor partial agonists for smoking cessation: carbon analogs of (-)-cytisine. Jotham W Coe et al Bioorg. Med. Chem. Lett. 15, 2974-9, (2005)

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6-(2-Phenylethyl)nicotine: a novel nicotinic cholinergic receptor ligand. Anna Ramunno et al Bioorg. Med. Chem. Lett. 15, 3237-40, (2005)

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The characterization of a novel rigid nicotine analog with alpha7-selective nAChR agonist activity and modulation of agonist properties by boron inclusion. Roger L Papke et al Bioorg. Med. Chem. Lett. 15, 3874-80, (2005)

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3-(2-Aminoethyl)pyridine analogs as alpha4beta2 nicotinic cholinergic receptor ligands. Małgorzata Dukat et al Bioorg. Med. Chem. Lett. 15, 4308-12, (2005)

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Epibatidine analogues as selective ligands for the alpha(x)beta2-containing subtypes of nicotinic acetylcholine receptors. Yiyun Huang et al Bioorg. Med. Chem. Lett. 15, 4385-8, (2005)

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3,5-Bicyclic aryl piperidines: a novel class of alpha4beta2 neuronal nicotinic receptor partial agonists for smoking cessation. Jotham W Coe et al Bioorg. Med. Chem. Lett. 15, 4889-97, (2005)

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6'-Methylpyrido[3,4-b]norhomotropane: synthesis and outstanding potency in relation to the alpha4beta2 nicotinic receptor pharmacophore model. David B Kanne et al Bioorg. Med. Chem. Lett. 15, 877-81, (2005)

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Extrapolation of human pharmacokinetic parameters from rat, dog, and monkey data: Molecular properties associated with extrapolative success or failure. Larry J Jolivette et al J. Pharm. Pharm. Sci. 94, 1467-83, (2005)

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Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. E Fontana et al Curr. Drug Metab. 6, 413-54, (2005)

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Synthesis and Pharmacological Evaluation of Novel 9- and 10-Substituted Cytisine Derivatives. Nicotinic Ligands of Enhanced Subtype Selectivity Chellappan, S. K.; et al. J. Med. Chem. 49, 2673-2676, (2006)

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Synthesis and pharmacological characterization of nicotinic acetylcholine receptor properties of (+)- and (-)-pyrido-[3,4-b]homotropanes. F Ivy Carroll et al J. Med. Chem. 49, 3244-50, (2006)

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Parallel artificial membrane permeability assay: a new membrane for the fast prediction of passive human skin permeability. Giorgio Ottaviani et al J. Med. Chem. 49, 3948-54, (2006)

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Synthesis and analgesic activity of secondary amine analogues of pyridylmethylamine and positional isomeric analogues of ABT-594. Chuan-Xin Zhang et al Bioorg. Med. Chem. Lett. 16, 2013-6, (2006)

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Aryloxyethylamines: binding at alpha7 nicotinic acetylcholine receptors. Hanan M Ragab et al Bioorg. Med. Chem. Lett. 16, 4283-6, (2006)

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Synthesis and alpha4beta2 nicotinic affinity of unichiral 5-(2-pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes. Marco Pallavicini et al Bioorg. Med. Chem. Lett. 16, 5610-5, (2006)

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Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)-bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors. J. Med. Chem. 50, 3627, (2007)

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Pharmacological characteristics and binding modes of caracurine V analogues and related compounds at the neuronal alpha7 nicotinic acetylcholine receptor. Anders A Jensen et al J. Med. Chem. 50, 4616-29, (2007)

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Design, synthesis, and preliminary pharmacological evaluation of new quinoline derivatives as nicotinic ligands. Luca Guandalini et al J. Med. Chem. 50, 4993-5002, (2007)

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Synthesis and structure-activity relationship studies of 3,6-diazabicyclo[3.2.0]heptanes as novel alpha4beta2 nicotinic acetylcholine receptor selective agonists. Jianguo Ji et al J. Med. Chem. 50, 5493-508, (2007)

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Synthesis and nicotinic acetylcholine receptor binding properties of bridged and fused ring analogues of epibatidine. F Ivy Carroll et al J. Med. Chem. 50, 6383-91, (2007)

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In silico and in vitro filters for the fast estimation of skin permeation and distribution of new chemical entities. Giorgio Ottaviani et al J. Med. Chem. 50, 742-8, (2007)

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Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds. Bram Baert et al Bioorg. Med. Chem. 15, 6943-55, (2007)

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Mapping the elusive neonicotinoid binding site. Motohiro Tomizawa et al Proc. Natl. Acad. Sci. U. S. A. 104, 9075-80, (2007)

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Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Jenny M Pedersen et al J. Med. Chem. 51, 3275-87, (2008)

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Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1. Gustav Ahlin et al J. Med. Chem. 51, 5932-42, (2008)

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Novel acetylcholine and carbamoylcholine analogues: development of a functionally selective alpha4beta2 nicotinic acetylcholine receptor agonist. Camilla P Hansen et al J. Med. Chem. 51, 7380-95, (2008)

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7-Azaindole derivatives as potential partial nicotinic agonists. Axel R Stoit et al Bioorg. Med. Chem. Lett. 18, 188-93, (2008)

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Preparation and affinity profile of novel nicotinic ligands. Yves Charton et al Bioorg. Med. Chem. Lett. 18, 2188-93, (2008)

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Parallel synthesis of a series of potentially brain penetrant aminoalkyl benzoimidazoles. I. Micco, et al., Bioorg. Med. Chem. 16, 2313-2328, (2008)

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Support vector machines classification of hERG liabilities based on atom types. Lei Jia et al Bioorg. Med. Chem. 16, 6252-60, (2008)

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Synthesis, nicotinic acetylcholine receptor binding, and pharmacological properties of 3'-(substituted phenyl)deschloroepibatidine analogs. F Ivy Carroll et al Bioorg. Med. Chem. 16, 746-54, (2008)

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Identification of "toxicophoric" features for predicting drug-induced QT interval prolongation. Alessio Coi et al Eur. J. Med. Chem. 43, 2479-88, (2008)

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Air to lung partition coefficients for volatile organic compounds and blood to lung partition coefficients for volatile organic compounds and drugs. Michael H Abraham et al Eur. J. Med. Chem. 43, 478-85, (2008)

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Phenotypic Characterization of Two Ancylostoma caninum Isolates with Different Susceptibilities to the Anthelmintic Pyrantel Steven R. Kopp, Glen T. Coleman, et al. Antimicrob. Agents Chemother. 52, 3980-3986, (2008)

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Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. R Scott Obach et al Drug Metab. Dispos. 36, 1385-405, (2008)

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Relationship between brain tissue partitioning and microemulsion retention factors of CNS drugs. Hong Wan et al J. Med. Chem. 52, 1693-700, (2009)

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Use of acetylcholine binding protein in the search for novel alpha7 nicotinic receptor ligands. In silico docking, pharmacological screening, and X-ray analysis. Chris Ulens et al J. Med. Chem. 52, 2372-83, (2009)

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Lipophilicity of basic drugs measured by hydrophilic interaction chromatography. Bruno Bard et al J. Med. Chem. 52, 3416-9, (2009)

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Octahydropyrrolo[3,4-c]pyrrole: a diamine scaffold for construction of either alpha4beta2 or alpha7-selective nicotinic acetylcholine receptor (nAChR) ligands. Substitutions that switch subtype selectivity. William H Bunnelle et al J. Med. Chem. 52, 4126-41, (2009)

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Side chain flexibilities in the human ether-a-go-go related gene potassium channel (hERG) together with matched-pair binding studies suggest a new binding mode for channel blockers. Ulrich Zachariae et al J. Med. Chem. 52, 4266-76, (2009)

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Physicochemical determinants of human renal clearance. Manthena V S Varma et al J. Med. Chem. 52, 4844-52, (2009)

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Gamma-lactams--a novel scaffold for highly potent and selective alpha 7 nicotinic acetylcholine receptor agonists. Albert Enz et al Bioorg. Med. Chem. Lett. 19, 1287-91, (2009)

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Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors. Kevin B Sippy et al Bioorg. Med. Chem. Lett. 19, 1682-5, (2009)

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Synthesis and SAR studies of 1,4-diazabicyclo[3.2.2]nonane phenyl carbamates--subtype selective, high affinity alpha7 nicotinic acetylcholine receptor agonists. Christopher J O'Donnell et al Bioorg. Med. Chem. Lett. 19, 4747-51, (2009)

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5-(2-Pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes: synthesis of all the stereoisomers and alpha4beta2 nicotinic affinity. Marco Pallavicini et al Bioorg. Med. Chem. Lett. 19, 854-9, (2009)

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Synthesis and biological evaluation of novel carbon-11 labeled pyridyl ethers: candidate ligands for in vivo imaging of alpha4beta2 nicotinic acetylcholine receptors (alpha4beta2-nAChRs) in the brain with positron emission tomography. Yongjun Gao et al Bioorg. Med. Chem. 17, 4367-77, (2009)

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Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain. Lei Du-Cuny et al Bioorg. Med. Chem. 17, 6983-92, (2009)

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Exploring QSAR and QAAR for inhibitors of cytochrome P450 2A6 and 2A5 enzymes using GFA and G/PLS techniques. Kunal Roy et al Eur. J. Med. Chem. 44, 1941-51, (2009)

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Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination. Manthena V S Varma et al J. Med. Chem. 53, 1098-108, (2010)

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Transient receptor potential ankyrin 1 (TRPA1) channel as emerging target for novel analgesics and anti-inflammatory agents. Pier Giovanni Baraldi et al J. Med. Chem. 53, 5085-107, (2010)

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alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) antagonists: from bench to bedside. Henri Mattes et al J. Med. Chem. 53, 5367-82, (2010)

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Chemistry and Pharmacological Characterization of Novel Nitrogen Analogues of AMOP-H-OH (Sazetidine-A, 6-[5-(Azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1-ol) as α4β2-Nicotinic Acetylcholine Receptor-Selective Partial Agonists Liu, J.; et al. J. Med. Chem. 53, 6973, (2010)

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Surface plasmon resonance biosensor based fragment screening using acetylcholine binding protein identifies ligand efficiency hot spots (LE hot spots) by deconstruction of nicotinic acetylcholine receptor ?7 ligands. Gerdien E de Kloe et al J. Med. Chem. 53, 7192-201, (2010)

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Novel α3β4 nicotinic acetylcholine receptor-selective ligands. Discovery, structure-activity studies, and pharmacological evaluation. N. Zaveri, et al., J. Med. Chem. 53, 8187-8191, (2010)

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A novel series of [3.2.1] azabicyclic biaryl ethers as alpha3beta4 and alpha6/4beta4 nicotinic receptor agonists. John A Lowe et al Bioorg. Med. Chem. Lett. 20, 4749-52, (2010)

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Lobeline esters as novel ligands for neuronal nicotinic acetylcholine receptors and neurotransmitter transporters. Marhaba Hojahmat et al Bioorg. Med. Chem. 18, 640-9, (2010)

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Discovery of {1-[4-(2-{hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl}-1H-benzimidazol-1-yl)piperidin-1-yl]cyclooctyl}methanol, systemically potent novel non-peptide agonist of nociceptin/orphanin FQ receptor as analgesic for the treatment of neuropathic pain: design, synthesis, and structure-activity relationships. Shigeo Hayashi et al Bioorg. Med. Chem. 18, 7675-99, (2010)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Synthesis of novel chiral ?2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes. Clelia Dallanoce et al Eur. J. Med. Chem. 45, 5594-601, (2010)

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Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 3'-(substituted phenyl)epibatidine analogues. Nicotinic partial agonists. F Ivy Carroll et al J. Nat. Prod. 73, 306-12, (2010)

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Discovery of isoxazole analogues of sazetidine-A as selective ?4?2-nicotinic acetylcholine receptor partial agonists for the treatment of depression. Jianhua Liu et al J. Med. Chem. 54, 7280-8, (2011)

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Unichiral 2-(2'-pyrrolidinyl)-1,4-benzodioxanes: the 2R,2'S diastereomer of the N-methyl-7-hydroxy analogue is a potent ?4?2- and ?6?2-nicotinic acetylcholine receptor partial agonist. Cristiano Bolchi et al J. Med. Chem. 54, 7588-601, (2011)

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Synthesis and biological activity of a novel class nicotinic acetylcholine receptors (nAChRs) ligands structurally related to anatoxin-a. Daniele Simoni et al Bioorg. Med. Chem. Lett. 21, 5423-7, (2011)

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QSAR-based permeability model for drug-like compounds. Rafael Gozalbes et al Bioorg. Med. Chem. 19, 2615-24, (2011)

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Acetylcholine binding protein (AChBP) as template for hierarchical in silico screening procedures to identify structurally novel ligands for the nicotinic receptors. Atilla Akdemir et al Bioorg. Med. Chem. 19, 6107-19, (2011)

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Translating Clinical Findings into Knowledge in Drug Safety Evaluation - Drug Induced Liver Injury Prediction System (DILIps). Zhichao Liu et al PLoS Comput. Biol. 7, e1002310, (2011)

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Structure-based design, synthesis and structure-activity relationships of dibenzosuberyl- and benzoate-substituted tropines as ligands for acetylcholine-binding protein. Ewald Edink et al Bioorg. Med. Chem. Lett. 22, 1448-54, (2012)

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SAR of ?7 nicotinic receptor agonists derived from tilorone: Exploration of a novel nicotinic pharmacophore. Michael R Schrimpf et al Bioorg. Med. Chem. Lett. 22, 1633-8, (2012)

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The pharmacology of (−)-nicotine and novel cholinergic channel modulators. Brioni, J.D., et al. Adv. Pharmacol. 37, 153-214, (1997)

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Autoradiographic comparison of [³H](−)nicotine[³H]cytisine and [³H]epibatidine binding in relation to vesicular acetylcholine transport sites in the temporal cortex in Alzheimer's disease. Sihver, W., et al. Neuroscience 94, 685-696, (1999)

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Heteromeric complexes of α5 and/or α7 subunits. Effects of calcium and potential role in nicotine-induced presynaptic facilitation. Girod, R., et al. Ann. N. Y. Acad. Sci. 868, 578-590, (1999)

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Nicotine and sympathetic neurotransmission. Haass, M., and Kubler, W., Cardiovasc. Drugs Ther. 10, 657, (1997)

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Pathological mutations of nicotinic receptors and nicotine-based therapies for brain disorders. Lena, C., and Changeux, J.P. Curr. Opin. Neurobiol. 7, 674-682, (1997)

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Merck 14,6524

Beil. 23,V,6,64

Aldrich MSDS 1, 1349:A / Corp MSDS 1 (2), 2541:A / FT-IR 2 (3), 3756:D / FT-IR 1 (2), 768:B / FT-NMR 1 (3), 294:B / IR-Spectra (3), 1328:G / NMR-Reference 2 (2), 647:B / RegBook 1 (2), 2525:K / Sax 6, 1997 / Sigma FT-IR 1 (1), 596:D / Structure Index 1, 398:E:6 / Vapor Phase 3, 1537:B