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N3876 Sigma

(−)-Nicotine

≥99% (GC), liquid

Synonym: (−)-1-Methyl-2-(3-pyridyl)pyrrolidine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine

  • CAS Number 54-11-5

  • Empirical Formula (Hill Notation) C10H14N2

  • Molecular Weight 162.23

  •  Beilstein Registry Number 82109

  •  EC Number 200-193-3

  •  MDL number MFCD00006369

  •  PubChem Substance ID 24897663

  • Popular Documents:  FTNMR (PDF)  

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Properties

Related Categories Agonists, Alkaloid, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology,
assay   ≥99% (GC)
form   liquid
optical activity   [α]20/D −169°(lit.)
color   yellow
refractive index   n20/D 1.5265(lit.)
solubility   ethanol: soluble50 mg/mL
density   1.010 g/mL at 20 °C(lit.)
Gene Information   human ... CHRNA2(1135), CHRNA3(1136), CHRNB2(1141), CHRNB4(1143), CYP2A6(1548), KCNH1(3756)
mouse ... Chrna7(11441), Chrnb1(11443)
rat ... Chrna1(79557), Chrna2(170945), Chrna4(25590), Chrna7(25302), Chrnb2(54239), Chrnb4(25103)

Description

Frequently Asked Questions

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Biochem/physiol Actions

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

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(−)-Nicotine solution

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Risk Statements (Europe) 
Safety Statements (Europe) 
36/37-45-61
RIDADR 
UN 1654 6.1 / PGII
WGK Germany 
3
RTECS 
QS5250000
Flash Point(F) 
213.8 °F
Flash Point(C) 
101 °C

Protocols & Articles

Articles

Determination of Water Content in Nicotine Using Karl Fischer Titration

Nitrogen compounds, acid amides and weakly basic amines (heterocyclenes) give no problems. They can be titrated according to the standard procedures. Strongly basic amines alter the pH value and must...
Keywords: Titrations

Peer-Reviewed Papers

References

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

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

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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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Nicotine metabolite ratio as an index of cytochrome P450 2A6 metabolic activity. Dempsey D, Tutka P, Jacob P, et al. Clin. Pharmacol. Ther. 76(1), 64-72, (2004)

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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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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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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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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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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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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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Assessing nicotine metabolism in pregnancy--a novel approach using hair analysis. Klein J, Blanchette P, and Koren G Forensic Sci. Int. 145(2-3), 191-4, (2004)

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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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Cytisine versus nicotine for smoking cessation. Walker N, Howe C, Glover M, et al. N. Engl. J. Med. 371(25), 2353-62, (2014)

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Nicotine improves obesity and hepatic steatosis and ER stress in diet-induced obese male rats. Seoane-Collazo P, Martínez de Morentin PB, Fernø J, et al. Endocrinology 155(5), 1679-89, (2014)

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Influential parameters on particle concentration and size distribution in the mainstream of e-cigarettes. Fuoco FC, Buonanno G, Stabile L, et al. Environ. Pollut. 184, 523-9, (2014)

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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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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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Efficacy of varenicline combined with nicotine replacement therapy vs varenicline alone for smoking cessation: a randomized clinical trial. Koegelenberg CF, Noor F, Bateman ED, et al. JAMA 312(2), 155-61, (2014)

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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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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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Physicochemical determinants of human renal clearance. Manthena V S Varma et al J. Med. Chem. 52, 4844-52, (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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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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Cytisine versus nicotine for smoking cessation. Zatoński W and Zatoński M N. Engl. J. Med. 372(11), 1072, (2015)

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The sleep-modulating peptide orexin-B protects midbrain dopamine neurons from degeneration, alone or in cooperation with nicotine. Guerreiro S, Florence C, Rousseau E, et al. Mol. Pharmacol. 87(3), 525-32, (2015)

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Cytisine--a tobacco treatment hiding in plain sight. Rigotti NA N. Engl. J. Med. 371(25), 2429-30, (2014)

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Electronic cigarettes for smoking cessation and reduction. McRobbie H, Bullen C, Hartmann-Boyce J, et al. Cochrane Database Syst. Rev. 12, CD010216, (2014)

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State laws prohibiting sales to minors and indoor use of electronic nicotine delivery systems--United States, November 2014. Marynak K, Holmes CB, King BA, et al. MMWR Morb. Mortal. Wkly. Rep. 63(49), 1145-50, (2014)

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Secondhand smoke exposure-induced nucleocytoplasmic shuttling of HMGB1 in a rat premature skin aging model. Chaichalotornkul S, Nararatwanchai T, Narkpinit S, et al. Biochem. Biophys. Res. Commun. 456(1), 92-7, (2015)

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VTA CRF neurons mediate the aversive effects of nicotine withdrawal and promote intake escalation. Grieder TE, Herman MA, Contet C, et al. Nat. Neurosci. 17(12), 1751-8, (2014)

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[Smoking cessation: varenicline/nicotine patch combination more effective than varenicline alone]. Steurer J Praxis (Bern 1994) 103(21), 1279-80, (2014)

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Accidental nicotine liquid ingestion: emerging paediatric problem. Gupta S, Gandhi A, and Manikonda R Arch. Dis. Child. 99(12), 1149, (2014)

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Drug-induced changes to the vertebral endplate vasculature affect transport into the intervertebral disc in vivo. Gullbrand SE, Peterson J, Mastropolo R, et al. J. Orthop. Res. 32(12), 1694-700, (2014)

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Confusion over electronic cigarettes continues. Mayo Clin. Health Lett. 32(7), 4, (2014)

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Water pipe smoking: not risk free. Peres J J. Natl. Cancer Inst. 106(8), doi:10.1093/jnci/dju275, (2014)

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[Advance in studies on dopamine system related genetic polymorphisms associated with nicotine dependence]. Wang C, Qian W, and Zhang M Zhonghua Yi Xue Yi Chuan Xue Za Zhi 31(3), 334-7, (2014)

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Newsmaker interview: Richard Carmona. A former surgeon general lends his support to e-cigarettes. Interview by Charles Schmidt. Carmona R Science 343(6171), 589, (2014)

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[Should we care about all people addicted to nicotine or just about those who smoke?]. Willers S Lakartidningen. 111(1-2), 38, (2014)

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The effects of nutritional deficiencies, smoking, and systemic disease on orthopaedic outcomes. Stephens BF, Murphy A, and Mihalko WM J. Bone Joint Surg. Am. 95(23), 2152-7, (2013)

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Sparking controversy. Rise in e-cigarette use has public health experts questioning their safety, effectiveness as harm-reduction device. Johnson SR Mod. Healthc. 43(38), 6-7, 12, 1, (2013)

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E-cigarettes: What's known, what's unknown. Rankin KV Tex. Dent. J. 130(5), 446-52, (2013)

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[Chronic administration of RJR-2403 in combination with low-dose of 17beta-estradiol corrects passive avoidance learning in ovariectomized rats]. Fedotova IuO and Sapronov NS Eksp. Klin. Farmakol. 76(5), 3-6, (2013)

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[The nicotine receptor as target for the improvement of cognitive symptoms in schizophrenia]. Quisenaerts C, Morrens M, and Sabbe B Tijdschr. Psychiatr. 55(6), 415-25, (2013)

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[Influence of agonist and antagonist Nalpha7-cholinoreceptors on active avoidance learning and gonadal hormones levels in ovariectomized female rats]. Fedotova IuO Ross. Fiziol. Zh. Im. I. M. Sechenova 99(4), 484-90, (2013)

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[Absorption, metabolism and excretion of nicotine in humans]. Sobkowiak R and Lesicki A Postepy Biochem. 59(1), 33-44, (2013)

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Effects of maternal nicotine exposure on expression of laminin alpha 5 in lung tissue of newborn. Mahdi Shariati K, Mohammad Reza N, Mehdi J, et al. Pak. J. Biol. Sci. 15(24), 1168-75, (2012)

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Smoking cessation treatment for COPD smokers: the role of pharmacological interventions. Jiménez-Ruiz CA and Fagerström KO Monaldi Arch. Chest Dis. 79(1), 27-32, (2013)

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Electronic cigarette: a possible substitute for cigarette dependence. Caponnetto P, Russo C, Bruno CM, et al. Monaldi Arch. Chest Dis. 79(1), 12-9, (2013)

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E-cigarettes, smokers and health policies. Nardini S and Pacifici R Monaldi Arch. Chest Dis. 79(1), 6-7, (2013)

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The influence of radioiodine therapy on ocular changes and their relation to urine cotinine level in patients with Graves' Ophthalmopathy. Czarnywojtek A, Zgorzalewicz-Stachowiak M, Budny B, et al. Neuro Endocrinol. Lett. 34(3), 241-8, (2013)

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[Immune to nicotine addiction?]. Schumacher B MMW Fortschr. Med. 155(5), 22-3, (2013)

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[Nicotine dependence and its molecular pharmacology]. Yoshimura R and Nakamura J Nihon Rinsho. 71(3), 473-6, (2013)

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[Smoking and alimentary diseases]. Tsujii M, Iijima H, Nishida T, et al. Nihon Rinsho. 71(3), 436-42, (2013)

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Nicotine and cotinine levels in blood and urine from forensic autopsy cases. Moriya F and Hashimoto Y Leg. Med. (Tokyo.) 6(3), 164-9, (2004)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Nicotine replacement therapy for smoking cessation. Stead LF, Perera R, Bullen C, et al. Cochrane Database Syst. Rev. 11, CD000146, (2012)

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Cortical control of VTA function and influence on nicotine reward. Wu J, Gao M, Shen JX, et al. Biochem. Pharmacol. 86(8), 1173-80, (2013)

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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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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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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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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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Implementation of a parental tobacco control intervention in pediatric practice. Winickoff JP, Nabi-Burza E, Chang Y, et al. Pediatrics 132(1), 109-17, (2013)

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Reducing the nicotine content to make cigarettes less addictive. Benowitz NL and Henningfield JE Tob. Control 22 Suppl 1, i14-7, (2013)

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(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function. Paul RK, Singh NS, Khadeer M, et al. Anesthesiology 121(1), 149-59, (2014)

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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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Nicotine aversion: Neurobiological mechanisms and relevance to tobacco dependence vulnerability. Fowler CD and Kenny PJ Neuropharmacology 76 Pt B, 533-44, (2014)

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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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Nicotine concentrations in urine and saliva of smokers and non-smokers. Feyerabend C, Higenbottam T, and Russell MA Br. Med. J. (Clin. Res. Ed.) 284(6321), 1002-4, (1982)

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Molecules and circuits involved in nicotine addiction: The many faces of smoking. Picciotto MR and Mineur YS Neuropharmacology 76 Pt B, 545-53, (2014)

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Prenatal cigarette smoke exposure: pregnancy outcome and gestational changes in plasma nicotine concentration, hematocrit, and carboxyhemoglobin in a newly standardized rat model. Farkas S, Hussein J, Ariano RE, et al. Toxicol. Appl. Pharmacol. 214(2), 118-25, (2006)

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The "stop" and "go" of nicotine dependence: role of GABA and glutamate. D'Souza MS and Markou A Cold Spring Harb. Perspect. Med. 3(6), doi:10.1101/cshperspect.a012146, (2013)

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Cholinergic control over attention in rats prone to attribute incentive salience to reward cues. Paolone G, Angelakos CC, Meyer PJ, et al. J. Neurosci. 33(19), 8321-35, (2013)

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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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Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Moyer TP, Charlson JR, Enger RJ, et al. Clin. Chem. 48(9), 1460-71, (2002)

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Tetrahydrobiopterin restores endothelial function in long-term smokers. Ueda S, Matsuoka H, Miyazaki H, et al. J. Am. Coll. Cardiol. 35(1), 71-5, (2000)

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Stimulation of the α7 nicotinic acetylcholine receptor protects against sepsis by inhibiting Toll-like receptor via phosphoinositide 3-kinase activation. Kim TH, Kim SJ, and Lee SM J. Infect. Dis. 209(10), 1668-77, (2014)

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Variability in the correlation between nicotine and PM2.5 as airborne markers of second-hand smoke exposure. Fu M, Martínez-Sánchez JM, Galán I, et al. Environ. Res. 127, 49-55, (2013)

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Drinking coffee and carbonated beverages blocks absorption of nicotine from nicotine polacrilex gum. Henningfield JE, Radzius A, Cooper TM, et al. JAMA 264(12), 1560-4, (1990)

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Cotinine, a neuroactive metabolite of nicotine: potential for treating disorders of impaired cognition. Terry AV, Hernandez CM, Hohnadel EJ, et al. CNS Drug Rev. 11(3), 229-52, (2005)

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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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Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. Zuccaro P, Altieri I, Rosa M, et al. J. Chromatogr. A 621(2), 257-61, (1993)

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Quantification of urinary o,o'-dityrosine, a biomarker for oxidative damage to proteins, by high performance liquid chromatography with triple quadrupole tandem mass spectrometry. A comparison with ion-trap tandem mass spectrometry. Orhan H, Coolen S, and Meerman JH J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 827(1), 104-8, (2005)

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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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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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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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Nicotine increases the resistance of lung cancer cells to cisplatin through enhancing Bcl-2 stability. Nishioka T, Luo LY, Shen L, et al. Br. J. Cancer 110(7), 1785-92, (2014)

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A therapeutic vaccine for nicotine dependence: preclinical efficacy, and Phase I safety and immunogenicity. Maurer P, Jennings GT, Willers J, et al. Eur. J. Immunol. 35(7), 2031-40, (2005)

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Potential substrates for nicotine and alcohol interactions: a focus on the mesocorticolimbic dopamine system. Doyon WM, Thomas AM, Ostroumov A, et al. Biochem. Pharmacol. 86(8), 1181-93, (2013)

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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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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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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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Quantitative analysis of catechol and 4-methylcatechol in human urine. Carmella SG, La Voie EJ, and Hecht SS Food Chem. Toxicol. 20(5), 587-90, (1982)

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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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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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Almond consumption reduces oxidative DNA damage and lipid peroxidation in male smokers. Li N, Jia X, Chen CY, et al. J. Nutr. 137(12), 2717-22, (2007)

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Tobacco-specific N-nitrosamine exposures and cancer risk in the Shanghai Cohort Study: remarkable coherence with rat tumor sites. Stepanov I, Sebero E, Wang R, et al. Int. J. Cancer 134(10), 2278-83, (2014)

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The effect of nicotine on choroidal thickness. Zengin MO, Cinar E, and Kucukerdonmez C Br. J. Ophthalmol. 98(2), 233-7, (2014)

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Gene amplification and microsatellite polymorphism underlie a recent insect host shift. Bass C, Zimmer CT, Riveron JM, et al. Proc. Natl. Acad. Sci. U. S. A. 110(48), 19460-5, (2013)

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Current status of immunologic approaches to treating tobacco dependence: vaccines and nicotine-specific antibodies. LeSage MG, Keyler DE, and Pentel PR AAPS J. 8(1), E65-75, (2006)

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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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Effects of nicotine on hippocampal and cingulate activity during smooth pursuit eye movement in schizophrenia. Tanabe J, Tregellas JR, Martin LF, et al. Biol. Psychiatry 59(8), 754-61, (2006)

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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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Simultaneous determination of mercapturic acids derived from ethylene oxide (HEMA), propylene oxide (2-HPMA), acrolein (3-HPMA), acrylamide (AAMA) and N,N-dimethylformamide (AMCC) in human urine using liquid chromatography/tandem mass spectrometry. Schettgen T, Musiol A, and Kraus T Rapid Commun. Mass Spectrom. 22(17), 2629-38, (2008)

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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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Nicotine signaling and progression of chronic kidney disease in smokers. Jain G and Jaimes EA Biochem. Pharmacol. 86(8), 1215-23, (2013)

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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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Validation of a screening questionnaire for a human milk bank to determine the presence of illegal drugs, nicotine, and caffeine. Escuder-Vieco D, Garcia-Algar Ó, Pichini S, et al. J. Pediatr. 164(4), 811-4, (2014)

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Shattuck Lecture. A molecular basis for nicotine as a gateway drug. Kandel ER and Kandel DB N. Engl. J. Med. 371(10), 932-43, (2014)

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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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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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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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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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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

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