Nicotine, reduction

Anaesthetised animal prejunctional Pressor response to nicotine reduction Ea-Kimetal., 1996... 

Egri, L. The chemical and physical factors in the nicotine reduction of tobaccos Proc. 6th Intemat. Tob. Sci. Cong., Tokyo, Japan (1976) 205-206. 

Stedman, R.L Nicotine reduction in tobacco smoke in Toward a less harmful cigarette, edited by E.L. Wynder and D. Hoffmann, Natl. Cancer Inst. Monograph 28 (1968) 113-119. 

The reactions of anabasine have been studied for many years by Russian chemists. Hydrogenation of 1-anabasine with Raney nickel in aqueous suspension gives dZ-a, -dipiperidyl in alkaline suspension the product is l-a,(8 -dipiperidyl 103). With hydrogen peroxide in acetic acid at 60° A-methylanabasine gives the A,A -dioxide which is reduced by sulfur dioxide to the py-A-oxide, in a manner analogous to nicotine. Reduction of the A,A -dioxide with zinc and hydrochloric acid gives back A-methylanabasine 104). 

Nicotinyl alcohol (3-pyridinylcarbinol, 3-pyridinemethanol) (27) has use as an antilipemic and peripheral vasodilator. It is available from either the reductions of nicotinic acid esters or preferably, the reduction of the nitrile to the amine followed by dia2otation and nucleophilic displacement. It is frequently adininistered in the form of the tartrate (Eig. 7). Nicotinic acid is frequently used as a salt in conjunction with basic dmgs such as the peripheral vasodilator xanthinol niacinate (28). Nicotinic acid and its derivatives have widespread use as antihyperlipidemic agents and peripheral vasodilators (1). 

The synthetic utility of radical cyclization was used as the key step in a four-step synthesis of the natural product (d,0-epilupinine (134b, a quinolizidine alkaloid) (75CB1043) from methyl nicotinate (146). Thus, l-(4-bromobutyl)-3-methoxycarbonyl-l,4,5,6-tetrahydropyridine (140), obtained from methyl nicotinate (146), was cyclized to 141 (43%), which on reduction with LiAlH4 in THF provided 134b in 95% yield (89T5269). 

Condensation of ethyl acetoacetate with phenyl hydrazine gives the pyrazolone, 58. Methylation by means of methyl iodide affords the prototype of this series, antipyrine (59). Reaction of that compound with nitrous acid gives the product of substitution at the only available position, the nitroso derivative (60) reduction affords another antiinflammatory agent, aminopyrine (61). Reductive alkylation of 61 with acetone in the presence of hydrogen and platinum gives isopyrine (62). Acylation of 61 with the acid chloride from nicotinic acid affords nifenazone (63). Acylation of 61 with 2-chloropropionyl chloride gives the amide, 64 displacement of the halogen with dimethylamine leads to aminopropylon (65). ... 

Niacin Nicotinic acid, nicotinamide Coenzyme in oxidation and reduction reactions, functional part of NAD and NADP Pellagra—photosensitive dermatitis, depressive psychosis... 

Niacin was discovered as a nutrient during studies of pellagra. It is not strictly a vitamin since it can be synthesized in the body from the essential amino acid tryptophan. Two compounds, nicotinic acid and nicotinamide, have the biologic activity of niacin its metabolic function is as the nicotinamide ring of the coenzymes NAD and NADP in oxidation-reduction reactions (Figure 45-11). About 60 mg of tryptophan is equivalent to 1 mg of dietary niacin. The niacin content of foods is expressed as mg niacin equivalents = mg preformed niacin + 1/60 X mg tryptophan. Because most of the niacin in cereals is biologically unavailable, this is discounted. 

Even more promising appears to be the selective reduction of TSNA by perforated cellulose acetate filter tips with higih air dilution. Although the smoker will compensate for the reduction in nicotine by smoking more intensely, it appears that the TSNA yield in smoke does, in this case, not increase to the level observed in smoke of an unperforated filter cigarette. 

Pictet, A. (1900) Ueber che Reduction des Nicotyrins zu inactivem Nicotin. Chemische Berichte, 33,2355-2356. 

Dehalogenation of aromatic amines using catalytic hydrogenolysis takes place easily, usually without the reduction of C=C, COO, C=N, and N02 groups.454,455 The hydrogenolysis of 5-bromo-3-(l-methyl-2-pyrrolidinyl)pyri-dine (38) on Pd/C in EtOH produces nicotine hydrobromide (39) (Scheme... 

Andersson K., Siegel R., Fuxe K., Eneroth P. (1983). Intravenous injections of nicotine induce very rapid and discrete reductions of hypothalamic catecholamine levels associated with increases of ACTH, vasopressin and prolactin secretion. Acta Physiol. Scand. 118, 35-40. 

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