Nicotine and Related Compounds

Domino EF (1999) Pharmacological significance of nicotine. In Gorrod JW, Jacob P (eds) Analytical determination of nicotine and related compounds and their metabolites. Elsevier, Amsterdam, pp 1-11... 

A series of reviews describing nicotine metabolism has recently appeared [2], Specific topics covered include the biosynthesis and metabolism of nicotine and related alkaloids [3], an overview of mammalian nicotine metabolism [4], the role of cytochrome P450 in nicotine metabolism [5], nicotine metabolism beyond cotinine [6], N-oxidation, A -methylation, and N-conjugation reactions of nicotine [7], extrahepatic metabolism of nicotine and related compounds [8], metabolism of the minor tobacco alkaloids [9], analysis and levels of nicotine and metabolites in body fluids [10], kinetics of nicotine and its metabolites in animals [11], pharmacokinetics of (S)-nicotine and metabolites in humans [12], and sources of inter-individual variation in nicotine pharmacokinetics [13]. Another recent review described variables which affect nicotine metabolism [14]. Several compilations of studies or reviews on the tobacco-specific A-nitrosamines are available [15-18]... 

Even some or most of the common garden vegetables and fruits contain trace amounts of alkaloids as well as other potentially beneficial types of compounds. Our daily cups of coffee contain the alkaloid caffeine. Tobacco and some other plants contain the alkaloid nicotine, and there is ongoing research to determine beneficial medicinal properties for nicotine and related compounds, possibly even against cancer. The alkaloid colchicine is sometimes used as a treatment for gout, although it is a drug also used in horticulture to induce mutations in plant species. 

Gorrod JW and Jacob P (eds.) (1999). Analytical Determination of Nicotine and Related Compounds and Their Metabolites. Elsevier, Amsterdam, The Netherlands. 

Hecht, S.S. and A.R. Tricker Nitrosamines derived from nicotine and other tobacco alkaloids Chapter 11 in Analytical determination of nicotine and related compounds and their metabohtes, edited by J.W. Gorrod and P. lacob III, Elsevier, New York NY (1999) 421 88. Hecht, S.S., T.C. Tso, and D. Hoffmann Approaches to the reduction of nitrosamines and aromatic amines in Modifying the risk for the smoker. Proc. 3rd World Conf. on Smoking and Health, edited by E.L. Wynder, D. Hoffmann, and G.B. Gori, 1975, DHEW Publ. No. (NIH) 76-1221 (1976) 535-545. 

Leiserson, L. and T.B. Walker Paper chromatography of nicotine and related compounds 8th Tobacco Chemists Research Conference, Program Booklet and Abstracts, Vol. 8, Paper No. 18, 1954, p. 6 Anal. Chem. 27 (1955) 1129-1130. 

Martin, and A. Rodgman Effect of treatment of tobacco with ammonia or various ammonium salts on the levels of pyridines and pyrazines in smoke RDR, 1976, No. 3, January 29, see www.ijrtdocs.com 501003985 -4047. Mizusaki, S., Y. Tanabe, M. Noguchi, and E. Tamaki Phytochemical studies on tobacco alkaloids. XIV. The occurrence and properties of putrescine V-methyltransferase in tobacco roots Plant Cell Physiol. 12 (1971) 633-640. Mozayani, A. Phencychdine Effects on human performance and behavior, Eorensic Sd. Rev. 15 (2002) 61-73. Pailer, M. Chemistry of nicotine and related compounds (including biosynthetic aspects) in Tobacco alkaloids and related compounds, edited by U.S. Von Euler, MacMillan, New York, NY (1965) pp. 15-36. Pictet, A. and A. Rotschy Synthese des Nikotins [Synthesis of nicotine] Chem. Ber. 37 (1904) 1225-1235. 

Pyridine-substituted nicotines, nornicotines, and anabasines are available from a-cyano-amines by a new synthesis. The syntheses of ( )-[l - N]nornicotine and ( )-[l - N]nicotine have been described, from cyclopropyl 3-pyridyl ketone and [ N]formamide. 4-Methylnicotine has been prepared it shows no nicotine-like pharmacological activity. " An investigation into the stereochemical factors involved in the behaviour of nicotine and related compounds in the Menschutkin reaction has been conducted.A bridged nicotine , 1,2,3,5,6,10b-hexahydropyrido[2,3-g]indolizine (44), has been synthesized by carboxylation of the dilithium derivative of 2-methylnornicotine followed by cyclisation and reduction with borane in tetrahydrofuran. Several 5-halogeno-nicotines have been prepared and their pK values and biological activities measured. ... 

Nicotinic acid and related compounds react with l-chloro-2,4-dinitrobenzene in the manner of the cyanogen bromide reaction to yield derivative I, which possibly also decarboxylates at elevated temperature. In alkaline medium this derivative first adds an hydroxyl ion and then undergoes ring opening to yield the colored derivative II. 

Murexine and related compounds have marked actions on the nicotine receptor as expected from choline esters (87-89). Toxins from the digestive glands of nudi-branchs have marked effects on the cardiovascular system of the rat (23). Antiviral and antibacterial substances have been obtained from molluscs (90,91). 

GOthert M, Duhrsen U (1979) Effects of 5-hydroxytryptamine and related compounds on the sympathetic nerves of the rabbit heart. Naunyn Schmiedebergs Arch Pharmacol 308 9-18 Gotti C, Zoli M, Clementi F (2006) Brain nicotinic acetylcholine receptors native subtypes and their relevance. Trends Pharmacol Sci 27 482-91 Grady SR, Meinerz NM, Cao J, Reynolds AM, Picciotto MR, Changeux JP, McIntosh JM, Marks MJ, Collins AC (2001) Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus a function mediated by a different nAChR than dopamine release from striatum. J Neurochem 76 258-68... 

Many drugs used for recreational as well as medical purposes can stimulate the central nervous system and so are referred to as stimulants. We separate. stimulants into tsvo groups according to their legal and social status. Controlled stimulants such as cocaine, amphetamines, methylphenidate (Ritalin), and related compounds are treated in this chapter, and over-the-counter stimulants such as nicotine and caffeine are dealt with in Chapters 7 and 8. We first consider the hi.story of stimulant use and discuss some of the effects of cocaine and the amphetamines as we review their history. Then we turn to a more detailed treatment of the pharmacology of these stimulants. 

Pilotti et al. carried out studies on the identification of tobacco alkaloids, their mammalian metabolites and related compounds by gas chromatography-mass spectrometry using packed columns (SE-30, SE-52 and Carbowax 20 M + KOH) and capillary columns (33 m - Emulphor 0 and 9.6 m - 0V-101). Various pyridine compounds, either identified or implied as intermediates in the manmalian metabolism of nicotine present in tobacco or tobacco smoke, were studied by GC-MS. Preliminary GC-MS experiments on the determination of nicotine using capillary columns in combination with multiple ion detection (MID) employing deuterated nicotine as internal standard were reported. The gas chromatographic data of the compounds investigated... 

Nicotine and related tobacco alkaloids produce their effects in biological systems by reacting at nicotinic acetylcholine receptors via the protonated N -alicyclic amino functional group. Compounds which are active tend to predominantly exist in the ionised form at physiological pH 7.4, whereas inactive compounds, such as cotinine, are virtually tmionised under these conditions. Unionised nicotine can pass freely across biological membranes in contrast to the ionised form where membrane transfer is greatly inhibited so that whilst nicotine is readily absorbed via the buccal cavity and intestine it is poorly absorbed from the acid environment of the stomach. 

Beilin, S.A. An evaluation of biological activity. I. Herbicidal action of nicotine derivatives and related compounds as determined by tests with Lemna Minor (Duckweed) RDR, 1964, No. 14, March 17, see www. rjrtdocs.com 500963430 -3445. 

The electrochemical properties of the surface molecules are explored by cyclic voltammetry (CV) and coulometry. The adsorption of various aromatic molecules on Pt(lll), Pt(l(X)) was studied (hydroquinone, 2,2, 5,5 -tetrahydroxybiphenyl, thiophenol and related compounds, pyridine, nicotinic acid, etc.). The nature and orientation of the surface species were determined. ... 

The IR-spectra of 41 tobacco alkaloids and related compounds have been tabulated (S5). Nornicotine, nicotine, myosmine, nicotyrine, anabasine, anatabine, and dihydronicotyrine were separated from an extract of tobacco alkaloids by countercurrent partition (86). Thin-layer chromatography has been used to separate nicotine, nornicotine, anabasine, and nicotyrine (57). The use of gas chromatography to separate tobacco alkaloids has been studied. The retention times of 11 tobacco alkaloids on polyethylene glycol columns has been reported (88) and the effect of the column packing on the retention times of pyridine bases has been described (89). Mixtures containing pyrrolidine, piperidine, pyridine, and various alkylated pyridines have been separated using programed temperature control (90). 

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