Anabasine

Anabasine.—5-Fluoronicotinic add [as (28)] is one of several unnatural substrates that have been metabolized by plants to alkaloid analogues cf. refs. 3 and 5. The major alkaloid of Nicotiana glauca is anabasine (33) it is essentially racemic. 5-Fluoronicotinic acid has been found recently to be converted into racemic 5-fluoroanabasine [as (33)] in this plant.  

Degradation of the anabasine gave results showing that over 14 

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Anabaena azollae Anabaena cylindrica Anabaena flos-aquae 0-anabasine [494-52-0] Anabasine [494-52-0] Anabolic steroids Anaerobic digestion Anaerobic treatment Anafranil... 

Mode of Motion. Nicotine, anabasine, and imidocloprid affect the ganglia of the insect central nervous system, faciUtating transsynaptic conduction at low concentrations and blocking conduction at higher levels. The extent of ionisation of the nicotinoids plays an important role in both their penetration through the ionic barrier of the nerve sheath to the site of action and in their interaction with the site of action, which is befleved to be the acetylcholine receptor protein. There is a marked similarity in dimensions between acetylcholine and the nicotinium ion. 

Ampicillin—see Penicillin, D-n-aminobenzyl-Amprolium coccidiostat mode of action, 1, 212 as veterinary product, 2, 515 Amquinsin, 2, 517 Amylobarbitone metabolism, 1, 237 Anabasine, 2, 511 synthesis, 2, 385 Anabasine, N-methyl-N -oxide... 

Anabasine, CmHj Na N-Methylanabasine, CuHigNj woNicoteine, CjoHiaNa Anatabine, C10H1.N,... 

Tobacco and its alkaloids have long ceased to have any therapeutic importance, but their extensive use as insecticides and the demand for nicotine for the manufacture of nicotinic acid have stimulated interest in processes of extraction and methods of estimation. On the latter subject there is a voluminous literature, of which critical resumes have been published by various authors.Recent work on this subject has been specially concerned with (1) the development of miero- and semi-miero-methods suitable for estimating nieotine in tobacco smoke and the distribution of nieotine on sprayed garden produce, in treated soils and in tobaeeo leaves,(2) the study of conditions necessary to ensure satisfactory results in using particular processes, " and (3) methods of separation and estimation of nicotine, nomicotine and anabasine in mixtures of these bases. ) In the United States and in Russia considerable interest is being shown in the cultivation of types of tobacco rich in nicotine, in finding new industrial uses for tobacco and its alkaloids, and in possible by-products from tobacco plants such as citric and malic acids, i " Surveys of information on tobacco alkaloids have been published by Jackson, i Marion and Spath and Kuffner. ... 

Nicotine may be detected by the colourless, crystalline mercurichloride obtained when an aqueous solution is added to a solution of mercuric chloride, by the black precipitate formed under similar conditions with potassium platinic iodide and the characteristic crystalline periodide, BI2. HI, m.p. 123°, produced on admixture, under specified conditions, 2 of ethereal solutions of nicotine and iodine (cf Anabasine, p. 43). A polarographic study of nicotine has been made by Kirkpatrick. ... 

Comparison of these results indicates identity of the two substances isolated independently by Orekhov and Ehrenstein, but Spiith and Kesztler have suggested that Pictet s nicoteine and Ehrenstein s base, consisted of impure Z-anatabine (p. 46). In this connection it may be noted that Ehrenstein s base was laevorotatory in acid solution, whereas Salts of anabasine are dextrorotatory. These authors have themselves isolated Z-anabasine from tobacco. The identity of synthetic 2-(3 -Pyridyl)piperidine with dZ-anabasine seems to have been definitely established. Anabasis aphylla is the source of the anabasine raanufac-... 

The action of anabasine is similar to that of nicotine. When the piperidine ring of anabasine is opened to produce 8-amino-8-3-pyridyl-n-valeric acid the activity is reduced, and this is also true of the corresponding lactam and the benzoyl derivative. According to De Eds myosmine is less toxic than nicotine but more active on isolated guinea-pig intestine. ... 

The acetylation of isotripiperideine by means of a ketone in nonpolar media affords a compound which decomposes in acidic media to piperideine and a monoacety.l derivative of the enamine form of tetrahydro-anabasine (195). This monoacetyl derivative is identical with the alkaloid amodendrine (312). A similar acylation with cinnamoylchloride affords the alkaloid orensine (196) (313), the optically active form of which is the natural alkaloid adenocarpine (314). The hydrolysis of alkaloid santiaguine gives a-truxilic acid (314). 

Mortimer, P. I. and Wilkinson, S. 1957. Occurrence of nicotine, anabasine, and isopeUetietine in Duboisia myoporoides. J. Chem. Soc. 3967-3970. 

Precursors and Formation. Tobaccos used for commercial products in the U.S.A, contain between 0,5 and 2,7% alkaloids. Nicotine constitutes 85-95% of the total alkaloids (14,26,27). Important minor alkaloids are nornicotine, anatabine, anabasine, cotinine and N -formylnornicotine (Figure 6), Several of these alkaloids are secondary and tertiary amines and, as such, amenable to N-nitrosation. The N-nitrosated alkaloids identified to date in tobacco and tobacco smoke include N -nitrosonornico-tine (NNN), 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone (NNK) and N -nitrosoanatabine (NAT Figure 7). In model experiments, nitrosation of nicotine also yielded 4-(methylnitrosamino)-4-(3-pyridyl)butanal (NNA 28). 

The primary psychoactive alkaloid in tobacco is nicotine (figure 4.9), occuring between 0.6 and 9.0% (Robbers et al. 1996 Gruenwald et al. 1998). Other alkaloids include nornicotine, N-formylnornicotine, cotinine, myosmin, )S-nicotyrine, anabasine, and nicotellin. Nicotine alone can produce the effects commonly associated with tobacco use, but other tobacco alkaloids are likely to contribute. 

Figure 2.1 Piperidine ring (a) and three functionalities of three carbons or larger that impart teratogenic activity (b) coniine, (c) anabasine, and (d) ammodendrine.

Figure 2.3 (a) Skeletal defects and (b) cleft palate induced in a newborn goat by maternal ingestion of coniine (Conium maculatum), anabasine Nicotiana glauca) or ammoden-drine Lupinus formosus). 

Figure 2.4 Piperidine teratogens (a) anabasine from Nicotiana glauca, and (b) ammodendrine from Lupinus formosus.

Nicotiana glauca and anabasine as a preferred test plant/alkaloid... 

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