Amide, Nicotinic Acid

Morpholine-N-dithiocarbinate S- Methyl-isothiocarbohydrazide Picolinic acid Nicotinic acid amide... 

Nicotinic acid amide p-Substituted acetoacetanilides 5-Nitrosalicylate... 

Pharmacology Niacinamide is synonymous with nicotinamide, 3-pyridine carboxamide, and nicotinic acid amide. Niacinamide is the amide of nicotinic acid (niacin, vitamin B3). Although nicotinic acid and nicotinamide function identically as vitamins, their pharmacologic effects differ. Nicotinamide does not have the hypolipidemic or vasodilating effects characteristic of niacin (nicotinic acid). 

Fig. 7.2. Phosphorus pent-oxide-mediated dehydration of nicotinic acid amide (A) to nicotinic nitrile (B) with the reagent forming polyphospho-ric acid (HP0 )r...

Synonyms. Niacinamide Nicotinic Acid Amide Nicotylamide Vitamin PP. 

The peculiarities of tryptophan metabolism in the 15 individual members of this family were demonstrated by oral ingestion of 10 g DL-tryp-tophan per test case and quantitative determination of the urinary content of kynurenine, 3-hydroxykynurenine, xanthurenic acid, nicotinic acid amide and its N -methyl derivative, and 4-pyridoxic acid. Of the 15 members of the family examined 6 showed, repeatedly, abnormal levels of... 

Dibromoacetonitrile reacts with morpholine to form bis(morpholino)acetonitrile (510 Scheme 93) 28,29,35,977 acrylonitriles (511) are cyclized to the imidazolines (512) by treatment with NCS and nicotinic acid amide, ... 

Niacinamide, U5P. Niacinamide, nicotinamide, nicotinic acid amide, is prepared by the amidation of esters of nicotinic acid or by pa.ssing ammonia gas into nicotinic acid at 320°C. Nicotinamide is a white cry.stalline powder that is odorless, or nearly so, and bitter. One gram is soluble in about I mL of water, I.S mL of alcohol, and about 10 mL of glycerin. Aqueous solutions aie neutral to litmus. For occurrence, action, and uses, see nicotinic acid. Niacinamide has pK values of O.. and 3.35. 

An important characteristic is the considerable increase in the band in 0.1 M acid (for example pheniramine maleate [308], nicotine [3003]). Some of these characteristics persist in the presence of functional groups, as in nicotinic acid and nicotinic acid amide [1802, 2805]. The narrow bands disappear in isonicotinic acid [2907]. In hydroxy-pyridine compounds [2806] the character of the spectrum changes completely, similar in some respects to the phenols (e. g. -> shift in alkaline solution). 

Niacin and niacinamide (nicotinamide and nicotinic acid amide) are converted to the ubiquitous redox coenzymes nicotinamide-adenine dinucleotide (NAD)" and nicotinamide-adenine dinucleotide phosphate (NADP). ... 

Use Solvent in synthesis of pharmaceuticals, resins, dyestuffs, rubber accelerators, insecticides, preparation of nicotinic acid and nicotinic acid amide, waterproofing agents, laboratory reagent. 

Tryptophan is an essential amino acid involved in synthesis of several important compounds. Nicotinic acid (amide), a vitamin required in the synthesis of NAD+ and NADP+, can be synthesized from tryptophan (Figure 17-24). About 60 mg of tryptophan can give rise to 1 mg of nicotinamide. The synthesis begins with conversion of tryptophan to N-formylkynurenine by tryptophan pyrrolase, an inducible iron-porphyrin enzyme of liver. N-Formylkynurenine is converted to kynurenine by removal of formate, which enters the one-carbon pool. Kynurenine is hydroxylated to 3-hydroxykynurenine, which is converted to 3-hydroxyanthranilate, catalyzed by kynureninase, a pyridoxal phosphate-dependent enzyme. 3-Hydroxyanthranilate is then converted by a series of reactions to nicotinamide ribotide, the immedi-... 

Figure 2.1.33 Rhombic channels of nicotinic-acid amide 47 (P2,/c) [74] along [010],...

Very prominent rhombic channels are seen in Fig. 2.1.33 along [010] of nicotinic-acid amide (vitamin B3) 47 that also exhibits smaller channels along [2-10] and [201], which should make it a good candidate for solid-state reactions. 

Plants of many genera produce compounds called alkaloids (alkali-like), and indeed all the thousands of known alkaloids contain nitrogen, by definition, and most are basic, and many are also toxic. Nicotine, a structurally simple example of an alkaloid, is a highly toxic substance, and is the major active component in tobacco (Nicotiam sp.), and amongst the most addictive drugs - an extraordinary contrast to the vital role in life played by nicotinic acid amide (32.2.1). Coniine, the active ingredient of hemlock (Conium maculatum), is another stmcturally simple example. 

UV-trace at 254 nm, (c) UV-trace at 340 nm, the wavelength of excitation, and (d) fluorescence emission above 350 nm. Approximately 1 nmole each of the following separands were injected 1 = thiamine Bl, 2 = pyrldoxamine B6, 3 = pyridoxine B6, 4 = pyridoxal B6 and 5 = nicotinic acid amide. Operational conditions appear in Table II. Reproduced with permission from Ref. 25. Copyright 1983 Elsevier. 

Benzonitrile acts in a similar way to form benzoic acid but requires sulfuric acid in the reacting mixture. Nicotinic acid amide (nicotinamide) has been prepared by the mild hydrolysis of 3-cyanopyridine, and acrylamide by the partial hydrolysis of acrylonitrile. Acrylonitrile may also be hydrolyzed to acrylic acid with mineral acids or with alkalies. Polyacrylonitrile is partially converted to the amide by nitric acid, and the nitrile oups of a number of polymers and copolymers have been hydrolyzed to amide and carboxylic acid groups to produce water-soluble polyelectrolytes. Isooyanides are stable toward alkalies but hydrolyze in the presence of acids to form an acid and an amine ... 

Anions of CH-acidic compounds add to pyridinium ions mainly at C-4. Substituents already present on pyridine can bring about interesting reaction sequences. This is exemplified by the formation of the 2,7-naphthyridine derivative 53 from the quaternary salt of the nicotinic acid amide 52 and malonic... 

A/-Alkyl-substituted nicotinic acid amides used as NAD models are selectively reduced in the 1,4-positions by Na2S204, e.g. 130 to 131. Initially, reaction with dithionite to give the base-stable sulfmate occurs ... 

Relation of nicotinic acid and nicotinic acid amide to canine black tongue. J. Amer. chem. Soc. 59, 1767 (1937). 

Vitamin B5 (nicotinic acid amide) and vitamin B6 (pyridoxal) are pyridine-based molecules, whereas vitamin B7 (biotin) is a bi-heterocycle fusing reduced imidazole and thiophene. 

Beta-picoline is similar to the olpho compound. It is soluble in water with which it forms o constant-boiling mixture it is also soluble in ethyl olcohol and ethyl ether. Suggested uses for it are in the manufacture of alkaloids, pharmaceuticals and rubber occeleratars. It is also o starting moterial for the production of nicotinic acid and nicotinic acid amide. 

CAS 98-92-0 EINECS/ELINCS 202-713-4 Synonyms Nicotinamide Nicotine acid amide Nicotinic acid amide Nicotinic amide Nicotylamidel... 

Nicotine acid. See Nicotinic acid Nicotine acid amide. See Niacinamide Nicotine alkaloid Nicotine liquid Nicotine solid. See Nicotine Nicotinic acid... 

Nickei carbonate, basic Nickel oxide (ous) nickei separation, from Co Dimethyi giyoxime nicotinamide source, multivitamins Niacinamide ascorbate nicotinic acid amide mfg. 

Synonyme Nicotinic acid amide niacinamide vitamin PP Trade namea ... 

Among 24 compounds containing the tetrazole function prepared by Holland and Pereira [70], 5-(3-pyridyl)-tetrazole (XIII) was found to depress plasma-free fatty acid levels in the fasted dog most effectively. The hypoHpidemic activity of XIII was comparable to that of nicptinic and 3-pyridyl-acetic acids. In fact, the duration of activity was approximately 5 hours which is three times longer than that of nicotinic acid. Moreover, no rebound effect was observed after the hypoHpidemic activity of XIII, while the short inhibitory action of nicotinic acid was followed by a rise of plasma-free fatty acid concentration above the control level in the fasted dog. In contrast, compound XIII was found to be about 3,000 times less potent than nicotinic acid in the in vitro test in which the inhibition of norepinephrine-induced free fatty acid release from isolated adipose tissue was measured. In this assay, 3-pyridyl-acetic acid (IV) was approximately 600 times less active than nicotinic acid. PicoHnic acid and isonicotinic acid were even less active. The metaboHtes of nicotinic acid in man, namely, nicotinic acid amide, iV -methylnicotinamide and nicotinuric acid, were found to be about 10,000 times less active as Hpolysis inhibitors than nicotinic acid. Based on these findings, 5-(3-pyridyl)-tetrazole... 

The name niacin is often used for two compounds, namely pyridine-3-carboxylic acid and pyridine-3-carboxylic acid amide. This confusion occurs because there is no consistency in the empirical nomenclature used in nutrition literature. Harris 1 lists niacin and niacinamide as the terms preferred in the United States, and nicotinic acid and nicotinic acid amide in the British literature. A convenient solution to the problem would be to use the term niacin to refer generically to the two compounds of nutritional significance as anti-pellagra factor and adopt the names nicotinic acid and nicotinamide to refer specifically to each. Nicotinamide has been adopted by the Commission for the Reform of Nomenclature in Biological Chemistry of the International Union of Pure and Applied Chemistry, and nicotinic acid is already in current use in most British, United States and other scientific literature in English. 

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