Nicotinamide
Title: Nicotinamide
CAS Registry Number: 98-92-0
CAS Name: 3-Pyridinecarboxamide
Additional Names: niacinamide; nicotinic acid amide
Trademarks: Nicobion (Merck KGaA); Papulex (Euroderma)
Molecular Formula: C6H6N2O
Molecular Weight: 122.12
Percent Composition: C 59.01%, H 4.95%, N 22.94%, O 13.10%
Literature References: Precursor of the coenzymes NAD and NADP, q.q.v. The terms niacin, Vitamin B3, and Vitamin PP have been used to refer to both nicotinamide and nicotinic acid, q.v. Isolation: H. v. Euler et al., Z. Physiol. Chem. 258, 212 (1939); P. Karrer, H. Keller, Helv. Chim. Acta 22, 1292 (1939). Prepn from 3-cyanopyridine: E. J. Gasson, D. J. Hadley, US 2904552 (1959 to Distillers). Alternately prepd by passing NH3 gas into molten nicotinic acid: A. Truchan, J. B. Davidson, US 2993051 (1961 to Cowles Chem.). Isoln and analysis by liquid chromatography: C. Bernofsky, Methods Enzymol. 66, 23 (1980). Extraction from cereal products: R. B. Roy, J. J. Merten, J. Assoc. Off. Anal. Chem. 66, 291 (1983). Toxicity data: F. G. Brazda, R. A. Coulson, Proc. Soc. Exp. Biol. Med. 62, 19 (1946). Clinical trial in acne: A. R. Shalita et al., Int. J. Dermatol. 34, 434 (1995); to preserve beta cell function in diabetes: P. Pozzilli et al., Diabetologia 38, 848 (1995). Review: "Niacin: Nicotinic Acid, Nicotinamide, NAD(P)" in Vitamins, W. Friedrich, Ed. (Walter de Gruyter, Berlin, 1988) pp 473-542. Comprehensive description: E. M. Abdel Moety et al., Anal. Profiles Drug Subs. 20, 475-555 (1991).
Properties: Needles from benzene, mp 128-131°. Distills at 150-160° at 5´10-4 mm Hg. Absorption spectrum: Kuhn, Vetter, Ber. 68, 2374 (1935). uv max: 261 nm (A1cm1% 451). pK (20°C): 3.3. One gram dissolves in about one ml water, in about 1.5 ml alcohol, in 10 ml glycerol. A 10% w/v soln in water is neutral to litmus. Forms cryst salts with acids. LD50 s.c. in rats: 1.68 g/kg (Brazda, Coulson).
Melting point: mp 128-131°
pKa: pK (20°C): 3.3
Absorption maximum: uv max: 261 nm (A1cm1% 451)
Toxicity data: LD50 s.c. in rats: 1.68 g/kg (Brazda, Coulson)
 
Derivative Type: Compd with ascorbic acid
CAS Registry Number: 1987-71-9
Additional Names: Nicotinamide ascorbate; nicoscorbine
Molecular Formula: C12H14N2O7
Molecular Weight: 298.25
Percent Composition: C 48.32%, H 4.73%, N 9.39%, O 37.55%
Literature References: Prepn: W. Wenner, J. Org. Chem. 14, 22 (1949).
Properties: Yellow crystals, mp 141-145°. [a]D20 +27.5° (c = 8 in H2O). pH of 5% aq soln ~4.0. Soly (20°): water 40%; abs ethanol 2.4%; methanol 10%. Sparingly sol in acetone. Practically insol in benzene, ether.
Melting point: mp 141-145°
Optical Rotation: [a]D20 +27.5° (c = 8 in H2O)
 
Therap-Cat: Antiacne; vitamin (enzyme cofactor).
Therap-Cat-Vet: Vitamin (enzyme cofactor).
Keywords: Enzyme Cofactor; Vitamin/Vitamin Source; Vitamin B3 (Niacin).

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