9693. Trigonellamide Chloride

Nomenclature

CAS number: 1005-24-9
3-(Aminocarbonyl)-1-methylpyridinium chloride; N1-methylnicotinamide chloride; 1-methylpyridine-3-carboxylic acid amide chloride; nicotinamide chloromethylate; nicotinamide methyl chloride.
C7H9ClN2O; mol wt 172.61.
C 48.71%, H 5.26%, Cl 20.54%, N 16.23%, O 9.27%.

Description and references

One of the principal excretion products of the metabolism of nicotinic acid in man, dog, and rat. Coenzyme action: Warburg, Christian, Biochem. Z. 287, 291 (1936). Synthesis by refluxing nicotinamide with methyl iodide in methanol, then shaking the nicotinamide methiodide with AgCl: Karrer et al., Helv. Chim. Acta 19, 826 (1936); and isolation from urine: Huff, Perizweig, J. Biol. Chem. 150, 395 (1943). Differentiation from NAD: Carpenter, Kodicek, Biochem. J. 46, 421 (1950). In vitro metabolism: G. S. Johnson, Eur. J. Biochem. 112, 635 (1980); H. Hoshino et al., Biochim. Biophys. Acta 801, 250 (1984). HPLC determn in urine: M. A. Kutnink et al., J. Liq. Chromatogr. 7, 969 (1984).

Chemical structure

Properties

Crystals from methanol. Dec 240°. Moderately sol in water. More sol in alcohol, butanol, isobutanol. Insol in amyl alcohol, octyl alcohol, benzene, chlorobenzene, chloroform. Destroyed upon boiling the aq soln, more rapidly in the presence of alkali. At room temp it is destroyed in alkaline soln. Reacts with ketones in aq alkaline soln to produce a greenish-blue fluorescence; on acidification the fluorescence changes to blue, and is intensified by heating.