Hydroxymethyl-nicotine

Derivatives of 11 are obtained by condensing the lactone of 2-(hydroxymethyl)nicotinic acid and aromatic aldehydes in the presence... 

A racemic nicotine analog, fra s-3-hydroxymethyl-nicotine, was converted to the hemisuccinate, which was conjugated to protein to form an immunogen (Fig. 4 [8c]). The resulting antiserum was used with tiitiated 1-nicotine as radioligand. With this radioligand the assay was highly selective for 1-nicotine, with less than 0,01% cross-reaction with d-nicotine. Similar enantioselectivity is claimed for 1-cotinine (42). 

Hybridomas producing monoclonal antibodies to S-nicotine were obtained from mice immunized with conjugated racemic 3 hydroxymethyl-nicotine. Affinity constants were around 10 with 4% cross-reaction to R-nicotine (67). 

Free-radical alkylation of (S)-nicotine (180) with alkanoic acids in the presence of ammonium peroxydisulfate and silver nitrate gives 6-alkyl-nicotines 181 as the major products (85S953). Radical hydroxymethylation of nicotine leads to 6-(hydroxymethyl)nicotine as well as a low yield of the isomeric 4-(hydroxymethyl)nicotine (86JOC1548). 

Ethers, esters, amides and imidazolidines containing an epithio group are said to be effective in enhancing the antiwear and extreme pressure peiformance of lubricants. Other uses of thiiranes are as follows fuel gas odorant (2-methylthiirane), improvement of antistatic and wetting properties of fibers and films [poly(ethyleneglycol) ethers of 2-hydroxymethyl thiirane], inhibition of alkene metathesis (2-methylthiirane), stabilizers for poly(thiirane) (halogen adducts of thiiranes), enhancement of respiration of tobacco leaves (thiirane), tobacco additives to reduce nicotine and to reduce phenol levels in smoke [2-(methoxymethyl)thiirane], stabilizers for trichloroethylene and 1,1,1-trichloroethane (2-methylthiirane, 2-hydroxymethylthiirane) and stabilizers for organic compounds (0,0-dialkyldithiophosphate esters of 2-mercaptomethylthiirane). The product of the reaction of aniline with thiirane is reported to be useful in the flotation of zinc sulfide. 

Chemical Name Nicotinic acid triester with 2-hexyl-2-(hydroxymethyl)-l,3-propanediol... 

Hexyl-2-(hydroxymethyl)-1,3-propanediol Nicotinic acid p-Toluenesulfonyl chloride... 

HeprOllicate. 3 -Pyrtd i n eca rbo.tylic acid 2-hexyl-2.((<3.pyridinylcarbonyl>oxy]methyl]-l,3-propanediyl ester nicotinic acid triester wilh 2-hexyl-2-(hydroxy,nethyl)-1.3-propanediot 2-hexyl-2-(hydroxymethyl)- [.3-propanediol trinicotinate 2.2-dihydroxymethyl -n-octano trinicotinate 1,1,1-trimethylolheptane trinicotinate 1,1,1 -(trihydroxy. methyi)heptane trinicotinate Meg rin. mol wt... 

It is very important to note that the solution of 2-hexyl-2-(hydroxymethyl)-1,3-propanediol in pyridine must be added to the solution of nicotinic acid, p-toluene sulphonyl chloride in pyridine almost dropwise with frequent stirring (below 80°C). 

The first experiments were carried out with nicotinic acid (61), and it was found that mitochondrial oxidation of cholesterol was enhanced in rats fed this compound. It was later found (62) that addition of nicotinic acid (8 X 10 moles, 10 mg) to the incubation mixture enhanced oxidation of cholesterol. Of a large series of nicotinic acid and nicotinamide homologues tested, only 3-pyridylacetic acid also stimulated oxidation of cholesterol (62,63). This compound has also been shown to be hypocholesterolemic in man (64,65). Pyridinol carbamate, 2,6-bis(hydroxymethyl)pyridine-di-A -methylcarbamate, fed to rats as 1 % of their diet also enhanced in vitro oxidation of cholesterol by rat liver mitochondria (66). 

Giorgy and his associates demonstrated that the administration of a factor referred to as vitamin 85 cures a scaly dermatitis of rats produced for the first time by Golderburger and Lily in 1926. The pellagralike dermatitis proved to be resistant to the administration of thiamine, nicotinic acid, and riboflavin. During the first five months of 1938, five different laboratories reported the crystallization and chemical identification of the vitamin. The vitamin was shown to be the 4,5-di-(hydroxymethyl)-3-hydroxy-2-methyl-pyridine. 

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