Nicotinic Acid
Title: Nicotinic Acid
CAS Registry Number: 59-67-6
CAS Name: 3-Pyridinecarboxylic acid
Additional Names: pyridine-b-carboxylic acid; P. P. factor; pellagra preventive factor; antipellagra vitamin; niacin
Trademarks: Niacor (Upsher-Smith); Niaspan (Kos); Nicangin (AstraZeneca); Nicobid (Aventis); Nicolar (Aventis); Niconacid (Novartis)
Molecular Formula: C6H5NO2
Molecular Weight: 123.11
Percent Composition: C 58.54%, H 4.09%, N 11.38%, O 25.99%
Literature References: Precursor of the coenzymes NAD and NADP, q.q.v. Widely distributed in nature; appreciable amounts are found in liver, fish, yeast and cereal grains. Dietary deficiency is associated with pellagra. The term "niacin" has also been applied to nicotinamide, q.v., or to other derivatives exhibiting the biological activity of nicotinic acid. Prepn by oxidation of alkyl b-substituted pyridines: A. Ladenburg, Ann. 301, 152 (1898). Synthesis from pyridine: S. M. McElvain, M. A. Goese, J. Am. Chem. Soc. 63, 2283 (1941). Prepn by oxidation of nicotine: S. M. McElvain, Org. Synth. coll. vol. I, 385 (1941); C. F. Woodward et al., Ind. Eng. Chem. 36, 540, 544 (1944). Toxicity study: F. G. Brazda, R. A. Coulson, Proc. Soc. Exp. Biol. Med. 62, 19 (1946). LC determn in foods: G. W. Chase, Jr. et al., J. AOAC Int. 76, 390 (1993). Lipid-modifying effect in diabetic patients: M. B. Elam et al., J. Am. Med. Assoc. 284, 1263 (2000). Review of nutritional requirements, bioavailability and relationship with tryptophan: W. J. Darby et al., Nutr. Rev. 33, 289-297 (1975); of biosynthesis, metabolism and physiological effects: L. M. Henderson, Annu. Rev. Nutr. 3, 289-307 (1983); of pharmacology and therapeutic uses: J. R. DiPalma, W. S. Thayer, ibid. 11, 169-187 (1991). Review: "Niacin: Nicotinic Acid, Nicotinamide, NAD(P)" in Vitamins, W. Friedrich, Ed. (Walter de Gruyter, Berlin, 1988) pp 473-542.
Properties: Needles from alcohol or water, mp 236.6°. Nonhygroscopic and stable in air. Sublimes without decompn. pKa 4.85. pH of satd aq soln 2.7. uv max: 263 nm, Hünecke, Ber. 60, 1451 (1927). One gram dissolves in 60 ml water. Freely sol in boiling water and in boiling alcohol, in alkali hydroxides and carbonates; sol in propylene glycol. Insol in ether. LD50 s.c. in rats: 5 g/kg (Brazda, Coulson).
Melting point: mp 236.6°
pKa: pKa 4.85
Absorption maximum: uv max: 263 nm, Hünecke, Ber. 60, 1451 (1927)
Toxicity data: LD50 s.c. in rats: 5 g/kg (Brazda, Coulson)
 
Derivative Type: N-Oxide see Oxiniacic Acid
 
Derivative Type: Sodium salt sesquihydrate
Trademarks: Direktan (Gerot)
Molecular Formula: C6H4NNaO2.1½H2O
Molecular Weight: 154.10
Percent Composition: C 46.76%, H 3.27%, N 9.09%, Na 14.92%, O 25.96%
Properties: White crystals or crystalline powder; stable in air. One gram dissolves in ~1.4 ml water, in ~60 ml alc, in 10 ml glycerol. Insol in ether. pH of aq soln: ~7.
 
Therap-Cat: Antilipemic; vitamin (enzyme cofactor).
Therap-Cat-Vet: Vitamin (enzyme cofactor).
Keywords: Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B3 (Niacin).

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