World Journal of Chemical Education. 2016, 4(3), 67-72
DOI: 10.12691/WJCE-4-3-4
Original Research

Nicotine and Colored Complexes

Giorgio Volpi1,

1Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy

Pub. Date: June 30, 2016

Cite this paper

Giorgio Volpi. Nicotine and Colored Complexes. World Journal of Chemical Education. 2016; 4(3):67-72. doi: 10.12691/WJCE-4-3-4

Abstract

An activity for nicotine extraction and detection in tobacco. The procedure is based on the extraction of nicotine from tobacco, followed by the reaction between nicotine with Co(II) and Cu(II) ions. A qualitative experiment is proposed in order to demonstrate and visualize the presence of nicotine in tobacco and to demonstrate metal-nicotine complexes formation and their mass spectrometry (ESI) analysis.

Keywords

nicotine, qualitative analysis, mass spectrometry (ESI), metal complex, naked-eye experiment, tobacco, first-year undergraduate/general, general public, high school/introductory chemistry

Copyright

Creative CommonsThis work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

References

[1]  Navaril R. M.; Laboratory Experiments Using Nicotine. J. Chem. Educ., 1974, 51(11), 749-750.
 
[2]  Benowi L.; Pharmacology of nicotine: addiction and therapeutics. Annu Rev. Pharmacol Toxicol, 1996, 36, 597-613.
 
[3]  Tapani T.; Johnsson T.; Reijula J.K.; Analysis of Nicotine, 3Hydroxycotinine, Cotinine, and Caffeine in Urine of Passive Smokers by HPLCTandem Mass Spectrometry. Clinical Chemistry, 1999, 45, 2164-2172.
 
[4]  Byrd G.D.; Davis R.A.; Ogden M.W.; A Rapid LC–MS–MS Method for the Determination of Nicotine and Cotinine in Serum and Saliva Samples from Smokers: Validation and Comparison with a Radioimmunoassay Method. J ChromatogrSci, 2005, 43(3), 133-140.
 
[5]  Hadidi A.; Faisal I. M.; Nicotine content in tobacco used in hubble-bubble smoking. Saudi Med. J.,2004; Vol. 25(7), 912-917.
 
[6]  Holladay M.W.; Dart M.J.; Lynch J.K.; Neuronal nicotinic acetylcholine receptors as targets for drug discovery. J. Med. Chem.1997, 40, 4169-4194.
 
[7]  Lloyd G.K.; Williams M.; Neuronal nicotinic acetylcholine receptors as novel drug targets. J. Pharmacol. Exp. Ther.2000, 292(2), 461-467.
 
[8]  Choi S.N.; Lee Y.M.; Lee H.W.; Nicotinium tetrachlorocuprate(II). Acta Crystallogr. Sect. E.-Struct Rep. Online 2002, 58, M583-M585.
 
[9]  Strickler M.; Goldstein B.M.; Maxfield K.; Shireman L.; Kim G.; Matteson D.S.; Jones J.P.; Crystallographic studies on the complex behavior of nicotine binding to P450cam (CYP101). Biochemistry2003, 42, 11943-11950.
 
[10]  Chohan ZH.; Rau A.; Noreen S.; Scozzafava A.; Supuran CT.; Antibacterial cobalt(II), nickel(II) and zinc(II) complexes of nicotinic acid-derived Schiff-bases. J Enzyme Inhib Med Chem. 2002, 17(2), 101-106.
 
[11]  Guan J.W.; FischerR.D.; Tris(indenyl)lanthanoid complexes (Ln = La, Pr, Nd) containing either (S)-(-)-nicotine or two simpler pyridine bases. Eur. J. Inorg. Chem.2001, 10, 2497-2508.
 
[12]  Sung-Kwon K., Hyun-Sook K.; Young-Inn K.; Preparation and Characterization of NicotiniumTetrahalocuprate(II) and Tetrahalocobaltate(II) Complexes: Structure of Nicotinium Tetrachlorocobaltate(II). Bull. Korean Chem. Soc. 2006, 27, 1877-1880.
 
[13]  Hirtenlehner C.; Monkowius U.; Syntheses, crystal structures and blue luminescence of Cu2X2(Ph3P)2[(−)-nicotine]2 (X=Br, I).Inorg. Chem. Commun. 2012, 109-112.
 
[14]  Gokhale N.; Padhye S.; Newton C.;, Pritchard R.; Hydroxynaphthoquinone metal complexes as antitumor agents x: synthesis, structure, spectroscopy and in vitro antitumor activity of 3-methyl-phenylazo lawsone derivatives and their metal complexes against human breast cancer cell line mcf-7. Met Based Drugs. 2000; 7(3), 121-128.
 
[15]  Swarts J. C.; Cook M. J.; Baker E. N.; Metal-Containing Proteins, Macrocycles, and Coordination Complexes in Therapeutic Applications and Disease. Met Based Drugs. 2008 Article ID 286363.
 
[16]  Montiel C.; Artalejo AR.; Sanchez-Garcia P.; Garcia AG.. 2 componenets in the adrenale nicotinic secretory response revealed by cobaltramps. Eur. J. of Pharmacol. 1993,230(1), 77-84.
 
[17]  Derdau V.; Laschat S.; Alkaloid N-oxide promoted asymmetric cobalt-mediated Pauson-Khand reaction. J. Organomet. Chem.2002, 642(1-2), 131-136.
 
[18]  Fasina T.M.; Ogundele O.; Ejiah F.N.; Dueke-Eze C.U.; Biological Activity of Copper (II), Cobalt (II) and Nickel (II) Complexes of Schiff Base Derived from O-phenylenediamine and 5-bromosalicylaldehyde. Int J Biol Chem.2012, 6(1), 24-30.
 
[19]  Zahid H. Chohan; Syed K. A. Sherazi;Biological Role of Cobalt(II), Copper(II) and Nickel(II) Metal Ions on the Antibacterial Properties of Some Nicotinoyl-Hydrazine Derived CompoundsMet Based Drugs. 1997, 4(2), 69-74.
 
[20]  Jasiewicz B.; Hoffmann M.; Gasowska A.; Jastrza R.; Malczewska-Jaskóa K.; Spectroscopic, Potentiometric and Quantum-Mechanical Studies of S-(-)-Nicotine Complexes with Cu(II) Ion. Acta Chim. Slov. 2014, 61, 137-144.
 
[21]  Muralidharan S.; Nagaraja KS.; Udupa MR.; Complexes of Cobalt(II), Nikel(II) and Copper(II) with nicotine. Indian J. Chem., Sect A. 1987, 26(4), 348-349.
 
[22]  Lay-Keow Ng.; Michel H.; Effects of moisture content in cigar tobacco on nicotine extraction Similarity between Soxhlet and focused open-vessel microwave-assisted techniques. Journal of Chromatography A. 2003, 1011, 213-219.
 
[23]  Tuomi T.; Johnsson T.; Reijula K.; Analysis of Nicotine, 3-Hydroxycotinine, Cotinine, and Caffeine in Urine of Passive Smokers by HPLC-Tandem Mass Spectrometry; Clin Chem.1999, 45(12), 2164-2172.
 
[24]  Manch W.; Fernelius WC.; The structure and spectra of nickel (II) and copper (II) complexes.J. Chem. Educ. 1961, 38(4), 192-201.
 
[25]  Cotton F.A.; Wilkinson G.; Advanced inorganic Chemistry, 4th ed.; John Wiley and Sons, New York, 1981.
 
[26]  Rodgers G. E.; Descriptive Inorganic, Coordination, and Solid-State Chemistry. 2nd ed.; McGraw-Hill, New York, 1994.
 
[27]  Boyd L.E.; The colorful Complexes of Copper(II). J. Chem. Educ., 1985, 62(9), 798.
 
[28]  Braish T. F.; Duncan R. E.; Harber J. J.; Steffen R. L.; Stevenson K. L.; Equilibria, spectra, and photochemistry of copper(I)-ammonia complexes in aqueous solution. Inorg. Chem., 1984, 23(24), 4072-4075.
 
[29]  Baker A.T.; The ligand field spectra of copper(II) complexes. J. Chem. Educ., 1998, 75(1), 98-99.