In 1940 Najjar and Wood (1) detected the presence of an unknown substance appearing in human urine after the ingestion of nicotinic acid and nicotinamide.This material was isolated from urine by Huff and Perlzweig (2, 3) and was shown to be the ion N1-methylpyridinium-3carboxylic acid amide, designat,ed as N1-methylnicotinamide (I in Fig. 1).In an investigation of the chemical properties of this substance it was observed that the quaternary ion form (I) is relatively unreactive, but that the a-carbinol (II) produced by the action of alkali on the quaternary ion is a very reactive substance.It was found to condense with a variety of alcohols, aldehydes, and ketones to yield highly fluor.escentderivatives.'Those formed with the alcohols are readily decomposed on acidification and are presumably carbinol ethers (III) of the type described by Decker and Kaufmann (4)) as formed by the cu-carbinols of the N-methylpyridines and N-methylquinolines with alcohols.However, the condensation products of N1-methylnicotinamide with certain aldehydes and ketones are quite stable and can be isolated in crystalline form.There are presented here the synthesis, properties, and the possible structure of a compound obtained when the cr-carbinol of N'-methylnicotinamide is condensed with acetone.2This reaction is the basis of new fluorometric methods for the quantitative estimation of Nl-methylnicotinamide in urine (6) and of the pyridine nucleotides in the blood cells (7).
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Jesse W. Huff (1947) studied this question.