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Nicotinic acid amide is the pyridine 3 carboxylic acid amide form of niacin.
Nicotinic acid amide is a water‑soluble vitamin that is not stored in the body.
The main source of vitamin in diet is in the form of nicotinamide, nicotinic acid, and tryptophan.
CAS Number: 98-92-0
EC Number: 202-713-4
IUPAC Name: pyridine-3-carboxamide
Chemical Formula: C6H6N2O
Other names: 98-92-0, 3-Pyridinecarboxamide, pyridine-3-carboxamide, Nicotinic acid amide, vitamin PP, Papulex, Aminicotin, Amixicotyn, Nicobion, Nicotylamide, Nikotinamid, Savacotyl, Benicot, Dipegyl, Endobion, Hansamid, Pelmine, Nicotinic amide, Delonin amide, Pelonin amide, Vi-Nicotyl, Austrovit PP, Inovitan PP, Nicosylamide, Nicotilamide, Nicotililamido, Amnicotin, Niacevit, Nicamina, Nicamindon, Nicofort, Nicomidol, Nicotamide, Nicovitina, Nicovitol, Nicozymin, Niocinamide, Niozymin, Niamide, Nicasir, Nicogen, Nicota, Nicotol, Nicovit, Niko-tamin, 3-Carbamoylpyridine, Nicotine acid amide, Nandervit-N, Pyridine-3-carboxylic acid amide, Vitamin B, Niavit PP, Nicotinamidum, Nicosan 2, Nicotine amide, beta-Pyridinecarboxamide, Nikotinsaeureamid, Nicotylamidum, Mediatric, Nicotinsaureamid, Pyridine, 3-carbamoyl-, 3-Pyridinecarboxylic acid amide, m-(Aminocarbonyl)pyridine, Acid amide, Factor pp, Nicotinamida, Nicovel, Vitamin B (VAN), Pelmin, Amid kyseliny nikotinove, Witamina PP, PP-Faktor, Amide PP, Nicotinsaureamid [German], Nikotinsaeureamid [German], Amid kyseliny nikotinove [Czech], Nicotinamidum [INN-Latin], Nicotinamida [INN-Spanish], NAM, Niacinamid, Nictoamide, CCRIS 1901, Dipigyl, HSDB 1237, Vi-noctyl, AI3-02906, NSC 13128, b-Pyridinecarboxamide, Niacinamide [USP], Nicotinamide [INN], 3-(aminocarbonyl)pyridine, MFCD00006395, NSC-13128, NSC-27452, .beta.-Pyridinecarboxamide, Nicotinamide (Vitamin B3), CHEMBL1140, MLS000069714, CHEBI:17154, 25X51I8RD4, NSC13128, Niacinamide (USP), NCGC00093354-03, NCGC00093354-05, SMR000058212, Nicotinamide 10 microg/mL in Acetonitrile, DSSTox_CID_929, Niacinamide;Nicotinic acid amide;Vitamin B3, WLN: T6NJ CVZ, DSSTox_RID_75873, DSSTox_GSID_20929, Niacinamide [USAN], Enduramide, CAS-98-92-0, B3, Vitamin, Vitamin B 3, B 3, Vitamin, 3 Pyridinecarboxamide, SR-01000721872, Nicotinsaureamid Jenapharm, EINECS 202-713-4, Jenapharm, Nicotinsaureamid, Niacotinamide, Nicotinamid, nicotin-amide, UNII-25X51I8RD4, Nicotinsaeureamid, 3-Amidopyridine, DEA No. 1405, Nicotinamide,(S), Vitamin B3 amide, 3-yridinecarboxamide, Mediatric (Salt/Mix), niacin - Vitamin B3, 1yc5, Opera_ID_775, Niacin (as niacinamide), NIACINAMIDE [II], Niacinamide(Vitamin B3), NIACINAMIDE [FCC], NICOTINAMIDE [MI], NIACINAMIDE [HSDB], NIACINAMIDE [INCI], NICOTINAMIDE [JAN], bmse000281, MolMap_000061, EC 202-713-4, NIACINAMIDE [VANDF], SCHEMBL2926, Nicotinamide (JP17/INN), NICOTINAMIDUM [HPUS], NIACINAMIDE [USP-RS], NICOTINAMIDE [MART.], MLS001424246, NICOTINAMIDE [WHO-DD], NICOTINAMIDE [WHO-IP], Nicotinamide-(amide-[15N]), SCHEMBL6278767, SGCUT00176, ZINC5878, TPN COMPONENT NIACINAMIDE, DTXSID2020929, SCHEMBL19978192, BDBM27507, NIACINAMIDE [ORANGE BOOK], Nicotinamide, niacin, vitamin B3, HMS2052M21, HMS2090B05, HMS2093H03, HMS2236J03, HMS3370F21, HMS3394M21, HMS3655M20, HMS3713B22, HMS3884A16, NICOTINAMIDE [EP IMPURITY], Pharmakon1600-01505397, NIACINAMIDE [USP MONOGRAPH], NICOTINAMIDE [EP MONOGRAPH], BCP07322, HY-B0150, NIACINAMIDE COMPONENT OF TPN, Nicotinamide (Vitamin B3) solution, NSC27452, to_000073, Nicotinamide 1.0 mg/ml in Methanol, Nicotinamide, >=98.5% (HPLC), Nicotinamide, >=99.5% (HPLC), Tox21_111202, Tox21_201716, Tox21_302776, NICOTINAMIDUM [WHO-IP LATIN], NSC759115, s1899, STL163867, AKOS005715850, Tox21_111202_1, CCG-101149, CS-1968, DB02701, NC00399, NSC-759115, SB74497, Nicotinamide, >=98% (HPLC), powder, NCGC00093354-04, NCGC00093354-06, NCGC00093354-09, NCGC00256432-01, NCGC00259265-01, NIACIN (AS NIACINAMIDE) [VANDF], AS-13845, BN166252, Nicotinamide, puriss., 99.0-101.0%, SY024804, Nicotinamide, tested according to Ph.Eur., SBI-0206826.P001, DB-057754, FT-0631517, FT-0672696, FT-0773644, N0078, N1651, SW197779-3, EN300-15612, Niacinamide, meets USP testing specifications, C00153, D00036, Nicotinamide (Niacinamide), analytical standard, AB00373895-13, AB00373895_15, AB00373895_16, Nicotinamide, Vetec(TM) reagent grade, >=98%, A845925, AC-907/25014114, Q192423, Q-201470, SR-01000721872-3, SR-01000721872-4, SR-01000721872-5, Z33546463, F2173-0513
The main source of niacin include meat, liver, green leafy vegetables, wheat, oat, palm kernel oil, legumes, yeast, mushrooms, nuts, milk, fish, tea, and coffee.
Nicotinic acid amide is a component of coenzyme I (nicotinamide adenine dinucleotide, NADP) and coenzyme II (nicotinamide adenine dinucleotide phosphate, NADP).
The nicotinamide part of these two coenzyme structures in human body has reversible hydrogenation and dehydrogenation characteristics.
Nicotinic acid amide plays a hydrogen transfer role in biological oxidation, can promote tissue respiration, biological oxidation process and metabolism, and is of great significance to maintain the integrity of normal tissues, especially skin, digestive tract and nervous system.
When lacking, pellagra is caused by the influence of cell respiration and metabolism.
Nicotinic acid amide is a white, crystalline powder.
Nicotinic acid amide is odorless or nearly so, and has a bitter taste.
Nicotinic acid amide's solutions are neutral to litmus.
One g dissolves in about 1 mL of water, in about 1.5 mL of alcohol, and in about 10 mL of glycerin.
Vitamin B3 was formerly called nicotinic acid; however, the term niacin is now preferred to avoid any confusion with the alkaloid, nicotine.
Nicotinic acid amide, also known as nicotinamide, refers to the amide derivative of niacin that is equivalent in vitamin activity.
Some texts use niacin to refer to nicotinic acid, niacinamide, and any derivatives with vitamin activity comparable to niacin.
Furthermore, research and chemistry-based resources use the terms nicotinic acid and nicotinamide; whereas pharmacy resources use niacin and niacinamide.
Nicotinic acid amide is a form of vitamin B3 found in food and used as a dietary supplement and medication.
As a supplement, Nicotinic acid amide is used by mouth to prevent and treat pellagra (niacin deficiency).
While Nicotinic acid amide may be used for this purpose, niacinamide has the benefit of not causing skin flushing.
As a cream, Nicotinic acid amide is used to treat acne.
Nicotinic acid amide is a water-soluble vitamin.
Nicotinic acid amide is the supplement name while Nicotinamide (NAM) is the scientific name.
Side effects are minimal.
At high doses liver problems may occur.
Normal amounts are safe for use during pregnancy.
Nicotinic acid amide is in the vitamin B family of medications, specifically the vitamin B3 complex.
Nicotinic acid amide is an amide of nicotinic acid.
Foods that contain Nicotinic acid amide include yeast, meat, milk, and green vegetables.
Nicotinic acid amide was discovered between 1935 and 1937.
Nicotinic acid amide is on the World Health Organization's List of Essential Medicines.
Nicotinic acid amide is available as a generic medication and over the counter.
Commercially, Nicotinic acid amide is made from either nicotinic acid (niacin) or nicotinonitrile.
In a number of countries grains have Nicotinic acid amide added to them.
Nicotinic acid amide Chemical Properties
Melting point: 128-131 °C(lit.)
Boiling point: 150-160 °C
Density: 1.40
Vapor density: 4.22 (vs air)
Vapor pressure: 0Pa at 25℃
Refractive index: 1.4660 (estimate)
Fp: 182 °C
Storage temp.: 2-8°C
Solubility: 691g/l
Form: powder
pka: 3.3(at 20℃)
Color: white
Odor: Odorless
PH: 6.0-7.5 (50g/l, H2O, 20℃)
PH Range: 9
Water Solubility: 1000 g/L (20 ºC)
Decomposition: >=200 °C
Merck: 14,6523
BRN: 383619
Stability: Stable. Incompatible with strong oxidizing agents.
InChIKey: DFPAKSUCGFBDDF-UHFFFAOYSA-N
LogP: -0.38 at 21℃
CAS DataBase Reference: 98-92-0(CAS DataBase Reference)
NIST Chemistry Reference:Nicotinic acid amide(98-92-0)
EPA Substance Registry System: Nicotinic acid amide (98-92-0)
Nicotinic acid amide is white needle crystal or crystalline powder, no smell or odor slightly, slightly bitter taste.
The relative density is 1.4, melting point is 131-132 ℃.
1 g of the above Nicotinic acid amide is soluble in 1 ml of water, 1.5 ml ethanol or 10 ml glycerin, insoluble in ether.
The pH of 10% aqueous solution is 6.5-7.5. in dry air to light and heat stability, in alkaline or acidic solution, heating generation to Nicotinic acid amide.
Rats by oral LD502.5-3.5g/kg ADI value does not make special provisions.
Uses
Nicotinic acid amide is a water-soluble B complex vitamin which is naturally present in animal products, whole cereals and legumes.
Together with Nicotinic acid amide, it belongs to vitamin B3 or vitamin PP, and is required as a nutrient to prevent the niacin deficiency disorder pellagra.
Nicotinic acid amide functions as a coenzyme or cosubstrate in many biological reduction and oxidation reactions required for energy metabolism in mammalian systems.
Nicotinic acid amide is used as a nutritional supplement, therapeutic agent, skin and hair conditioning agent in cosmetics, and a constituent of consumer household solvent and cleaning products and paints.
Nicotinic acid amide is approved for use by the FDA as a food additive to enrich corn meal, farina, rice, and macaroni and noodle products.
Nicotinic acid amide is also affirmed as GRAS (Generally Recognized as Safe) by the FDA as a direct human food ingredient which includes its use in infant formula.
Nicotinic acid amide is approved for use in pesticide products applied to growing crops only as a synergist with a maximum limitation of 0.5% of formulation.
Nicotinic acid amide is a nutrient and dietary supplement that is an available form of niacin.
Nicotinic acid amide is pyridine beta-carboxylic acid and nicotinamide, which is another term for niacinamide, is the corresponding amide.
Nicotinic acid amide is a powder of good water solubility, having a solubility of 1 g in 1 ml of water.
Unlike niacin, Nicotinic acid amide has a bitter taste; the taste is masked in the encapsulated form.
Used in fortification of cereals, snack foods, and powdered beverages.
Nicotinic acid amide is used as food additive, for multivitamin preparations and as intermediate for pharmaceuticals and cosmetics.
Manufacturing Process
Gaseous ammonia was passed into nicotinic acid at a temperature between 200-235°C until the conversion to nicotinamide was 85%.
The reaction mixture was colored light brown.
The reaction mass was cooled and grounds to a fine powder.
Fifty grams of this crude nicotinamide were boiled with 500 ml of anhydrous ethyl acetate until a dark solution was.
A little solid remained in suspension.
Gaseous ammonia was passed in below the surface of the ethyl acetate at a temperature between 60-70°C.
After a short time ammonium nicotinate started to precipitate out of solution as a brown solid.
Sufficient gaseous ammonia, was passed into the ethyl acetate solution to insure complete precipitation of the nicotinic acids as ammonium nicotinate.
The solution was filtered at about 60-70°C.
The filter cake consisted of ammonium nicotinate, which, upon drying, weighed 12.4 grams.
The filtrate was stirred arid boiled for 20 minutes with one-half gram of activated carbon and two grams of activated adsorbent clay.
The mixture was filtered hot.
The filtrate was boiled twenty minutes with one-half gram of activated carbon and two grams of activated adsorbent clay and then filtered hot.
The carbon and clay treatment was repeated once more.
The final filtrate was cooled slowly with stirring to room temperature to precipitate white crystalline nieocinamide which, upon drying, weighed 26.7 grams and had a melting point of 129.5°C, and was over 99 percent pure.
The mother liquor from the above filtration was boiled down to one-third of its volume and cooled to room temperature.
A second crop of nicotinamide of three grams was obtained.
Synthesis
β-methyl pyridine is oxidized to nicotinic acid by air, and the latter is produced by the action of ammonium hydroxide, and then heating and dehydration.
Nicotinic acid, boric acid and ammonia into reaction pot, stirring at the condition of ammonia gas, heating dissolution; then distilled ammonia recovery, to 120℃ after the immigration dewatering pot continues to enrich; when the temperature reached 145 ℃, start adding liquid ammonia, and in 185 to 190℃ to ammonia reaction 20～30h.
And then cooled to 130℃, diluted with distilled water, activated carbon was added, and in 70~80℃through ammonia decolorization 2h; reaction after filtered, , filtrate in 24 hours after analysis of cold water, fractional crystallization and washing with ethanol, and drying to obtain the finished product.
The yield was 89%.
From the nicotinic acid and ammonia react into salt and then dehydrated.
Clinical Use
Nicotinic acid amide is used in the treatment of niacin deficiency, which is referred to as pellagra (from the Italian, pelle for “skin” and agra for “dry”).
The major systems affected are the gastrointestinal tract (diarrhea, enteritis and stomatitis), the skin (dermatitis), and the CNS (generalized neurological deficits including dementia). Pellagra has become a rare condition in the United States and other countries that require or encourage enrichment of wheat flour or fortification of cereals with Nicotinic acid amide.
Because the nucleotide form can be synthesized in vivo from tryptophan, pellagra is most often seen in areas where the diet is deficient in both niacin and tryptophan.
Typically, maize (corn)-based diets meet this criteria.
Nicotinic acid amide deficiency can also result from diarrhea, cirrhosis, alcoholism, or Hartnup disease.
Nicotinic acid amide is interesting that niacin deficiency can also, rarely, result from vitamin B6 deficiency (see Vitamin B6 section).
Nicotinic acid amide, but not niacinamide, is also one of the few vitamins that are useful in the treatment of diseases unrelated to deficiencies.
