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Alkaloids of tobacco

Af-oxides of nicotine - both cis- and trans- isomers - are widely distributed throughout the various parts of tobacco plants (J.D, Phillipson and S.S. Hands, Phytochem., 1975, [Pg.183]

and iV-acylated derivatives of nornicotine have been isolated from Nicotiana tabacum. These include the N-fo-rmyl and W-acetyl compounds,and others bearing n-hexanoyl and n-octanoyl side chains (A.J.N. Bolt, Phytochem., 1972, [Pg.183]

New alkaloids from N.tabacum include compounds (54) and (55) (E. Demole and C. Demole, Helv., 1975, 58, 523). [Pg.183]

Additionally 5-methyl-2,3 -bipyridyl (56) is also present in some varieties of N.tabacum (A.H. Warfield, W.D. Galloway and A.G. Kallianos, Phytochem., 1972, 11, 3371). [Pg.183]

A versatile short synthesis of the tobacco alkaloids has been developed (G.F. Alberici et al., Tetrahedron Letters, 1983, [Pg.184]


Alkaloids of Tobacco Smoke. The following alkaloids, apart from normal alkaloidal constituents of tobacco, have been isolated by Wenusch and Schoeller from tobaceo smoke. [Pg.46]

The 13C n.m.r. spectra of nicotine metabolites have been measured and discussed.39 The stereoselectivity of the iodomethylation of nicotine and seven analogues has been studied with the aid of 13C n.m.r. spectroscopy.40 Nicotine yields 2-methylnicotine as the major product when treated with methyl-lithium or methyl radicals, accompanied, as reported earlier, by 4- and 6-methylnicotine. Nicotine tV-oxide and methylmagnesium bromide afford 2- and 6-methyl-nicotines.41 Anabaseine (26), a well-known minor alkaloid of tobacco, has been identified as a poison-gland product in ants of the genus Aphaenogaster, which use it as an attractant.42... [Pg.44]

Anatabine (177) and A -methylanatabine are minor alkaloids of tobacco.1 5-167 Racemic 177 was synthesized by the BF3-catalyzed condensation (cf. Section II, A) of diethyl 3-pyridylmethylenebis-carbamate (176) with 1,3-butadiene and subsequent removal of the JV-ethoxycarbonyl group.168,169... [Pg.97]

The enantioselective total syntheses of several piperidine and pyrrolidine alkaloids of tobacco were accomplished in the laboratory of J. Lebreton. ° In the final stage of the total synthesis of (S)-A/-methylanabasine, a one-pot Cbz-deprotection-hydrogenation-Eschweiler-Clarke methylation was carried out using a HCHO/MeOH/Pd(C)/H2 system at room temperature with an overall 88% yield. [Pg.161]

The restricted space available for these Reports unfortunately does not allow the discussion of a number of topics of interest to monoterpenoid chemists useful reviews of such topics include monoterpenoid alkaloids/ carbazole alkaloids/ isoprenoids and alkaloids of tobacco/" naturally occurring plant coumarins/ the biosynthesis of aromatic hemiterpenes/ and recent developments in the field of naturally occurring aroma components/ The poor quality of the Chemical Abstracts makes it difficult to assess the significance of a number of reviews of potential industrial interest/ A volume in the Methodicum Chimicum series includes a very brief discussion of some monoterpenoids/"... [Pg.4]

The structures of some of the most common tobacco alkaloids found in smoke are shown in Figure XVII.B-3. The transfer rate for nicotine is generally about 10% to 12% but a number of factors, including the cut width of the tobacco, the shape of the cigarette, the moisture content of the tobacco, and various tobacco additives can significantly affect nicotine delivery to mainstream smoke [Kuhn and Klus (2231), Hecht et al. (1580)]. Many of the alkaloids of tobacco smoke consist of components originally in the tobacco, which transfer unchanged, and various pyrolysis products of the nicotine alkaloids. [Pg.789]

Quin, L.D. Alkaloids of tobacco smoke. I. Fractionation of some tobacco alkaloids and of the alkaloid extract of bnrley cigarette smoke by gas chromatography J. Org. Chem. 24(1959)911-914. [Pg.1383]

Binder, A.R. Alkaloids of tobacco in Chemistry of carbon compounds A modem comprehensive treatise, Volume TV, Part C, Heterocyclic compounds, edited by E.H. Rodd, Elsevier, Amsterdam (1960) pp. 1818-1823. [Pg.1448]

B31. Leete, E Biosynthesis of the minor alkaloids of tobacco ... [Pg.1459]

Comparatively few pyrrolidine alkaloids have been found to occur naturally. The parent substance is a constituent of Daucm carota L. (2) and is one of the minor alkaloids of tobacco. The presence of pyrrolidine in tobacco was established by characterization of this base (1) through its chloroaurate, C4H9N HCl AuCh, bright yellow plates, m.p. 206° (dec) and its chloroplatinate (C4H9N HCl)2PtCl4, as orange prisms which darken at 190° and melt with decomposition at 199°. It also forms a crystalline hydrochloride which sublimes on heating, and this in turn can be converted to a liquid nitrosamine by treatment with sodium nitrite. [Pg.91]

Although Z-nicotine is the major alkaloid of tobacco, a number of other bases have been reported as occurring with it such as nicotimine, nicoteine, and nicotelline (259, 260, 261) to which Noga later added two more isonicoteine and nicotoine (261). It is now known that nicoteine was a mixture (262) and the homogeneity of nicotimine is extremely doubtful. The latter was considered to be 3 -pyridyl-2-piperidine, but its properties do not agree with those of that compound now known to be identical with anabasine. Furthermore, isonicoteine has been shown to be identical with 3, 2-dipyridyl (263). [Pg.228]

Nicotine, C10H14N2, is the alkaloid of tobacco. It is a liquid which boils at 247° and is miscible with water it is... [Pg.585]

Tobacco aBaloMa. Collective name for alkaloids of tobacco plants (genus Nicotiana, Solanaceae). Structure occurrence All T. a. contain a pyridine ring they are therefore also occasionally known as pyridine alkaloids. Almost all T. a. are 3-pyridyl derivatives, the main alkaloid is nicotine which is accompanied by a series of minor alkaloids such as nor-nicotine, "anabasine, cotinine, nicotyrine, and nic-otelline (CijHnNj, Mr 233.27, mp. 147-148°C, see figure). Their occurrence is typical for the genus Ni-... [Pg.654]

Enzell CR, Wahlberg I, Aasen AJ (1977) Isoprenoids and alkaloids of tobacco. Prog Chem Org Nat Prod 34 1-79... [Pg.150]

Nicotine belongs to the Solanaceae (nightshade family) alkaloids. It is the principal alkaloid of tobacco, but occurs also as a trace component in Acacia, Sedum, Erythroxylum, Equisetum and Lycopodium species. The two economically most important tobacco species are Nicotiana tabacum (Virginia tobacco), which grows up to 3 metres in height, has reddish flowers and lancet-shaped, pointed leaves, and the 1.2-metre high Nicotiana rustica species (known in South America as Mapacho and in Vietnam as Thuoc Lao), with greenish-yellow flowers and egg-shaped leaves (Fig. 5.204). [Pg.483]

Nornicotine and anabasine count amongthe minor alkaloids of tobacco. Whereas Nkotiana species contain the (S)-nornicotine, Duboisia hopwoodii produces the (J )-enantiomer. Anabasine is with up to 2.6% the principal alkaloid of Anabasis aphylla. The anabasine content in Nkotiana glauca is comparatively high and reaches 1 %. [Pg.490]

Anatabine is the most abundant of the minor alkaloids of tobacco. It has been established that both rings of this alkaloid are derived from the dimerization of nicotinic acid (Figure 6.9) [36, 37]. [Pg.542]

The main alkaloid of tobacco, Nicotiam tabacum (Solanaceae), is (-)-nicotine, as described in Section 3.1. (-)-Nicotine is an alkaloid composed of nicotinic acid (which will be described later) and a pyrrolidine ring derived from ornithine. [Pg.134]

Nicotine is the main alkaloid of tobacco Nicotiana tabacum) of the Solana-ceae. Anabasine is the main alkaloid of Anabasis aphylla (Chenopodiaceae), although trace amounts are also present in tobacco. Both nicotine and anabasine possess strong insecticidal activity. The structures of these alkaloids also have similarities in that one contains a pyrrolidine ring derived from ornithine and the other a piperidine ring derived from lysine, both of which are joined at C-3 of the pyridine ring, itself derived from nicotinic acid [1]. These alkaloids were described in detail in Chapters 3 and 4 on ornithine-and lysine-derived alkaloids, respectively. The procedure for the formation of nicotine and anabasine by condensation of A -pyrrolidine and A -piperidine with a nicotinic acid moiety is shown in the figure [2]. [Pg.184]

Anatabine is one of the principal additional alkaloids of tobacco [5]. The absolute configuration of this alkaloid was deduced to be S [5], and the synthesis of the racemate was achieved [6]. [Pg.185]

Dwoskin LP, Teng L, Buxton ST, Ravard A, Deo N, Crooks PA (1995) Minor alkaloids of tobacco release [ H]dopamine fi om superfused rat striatal slices. Eur J Pharmacol 276 195-199... [Pg.1362]

Contents C. R. ENZELL, I. WAHLBERG, and A. J. AASEN, Iso-prenoids and Alkaloids of Tobacco - A. R. PIN DER, The Chemistry of the Eremophilane and Related Sesquiterpenes - D. GROSS, Phyto-alexine und verwandte Pfianzenstoffe - K. H. OVERTON and D. J. PICKEN, Studies in Secondary Metabolism with Plant Tissue Cultures - D. P. CHAKRABORTY, Carbazole Alkaloids - J. JACOB, Burzeldriisenlipide - W. VOELTER, Hypothalamus-Regulationshor-mone - Author Index - Subject Index. [Pg.590]

Solution of Nicotine Sulphate, 5. Contains 40 0 per cent of the alkaloids of tobacco. [Pg.441]


See other pages where Alkaloids of tobacco is mentioned: [Pg.35]    [Pg.813]    [Pg.858]    [Pg.183]    [Pg.99]    [Pg.780]    [Pg.791]    [Pg.1306]    [Pg.1380]    [Pg.1458]    [Pg.228]    [Pg.247]    [Pg.459]    [Pg.482]    [Pg.164]    [Pg.165]    [Pg.198]    [Pg.500]    [Pg.418]    [Pg.442]   


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