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Nicotinamide

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CAS:98-92-0
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Nicotinamide Basic information
description Chemical Properties Uses Toxicity Synthesis
Product Name:Nicotinamide
Synonyms:NicotinamideForBiochemistry;NicotinamideB.P.,U.S.P.;Niacinamide/Nicotinamide;Nicotinamide(Niacinamide)Nicotinamide(Niacinamide)Bp/Usp;Nicotinamide,98%;Vitamin B3;Nicotinamidum;NIACINAMIDE USP GRANULAR
CAS:98-92-0
MF:C6H6N2O
MW:122.12
EINECS:202-713-4
Product Categories:Inhibitors;Cosmetics;Vitamin Ingredients;Vitamin series;food additive;Cosmeitc raw materials;Nutritional Supplements;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;vitamin;Other APIs;Biochemistry;Vitamins;Vitamins and derivatives;Miscellaneous Compounds;Aromatics;Nicotine Derivatives;Pharmaceutical intermediates
Mol File:98-92-0.mol
Nicotinamide Structure
Nicotinamide Chemical Properties
Melting point 128-131 °C(lit.)
Boiling point 150-160 °C
density 1.40
vapor density 4.22 (vs air)
refractive index 1.4660 (estimate)
Fp 182 °C
storage temp. 0-6°C
solubility 691g/l
form powder
pka3.3(at 20℃)
color white
OdorOdorless
PH6.0-7.5 (50g/l, H2O, 20℃)
PH Range9
Water Solubility 1000 g/L (20 ºC)
Decomposition >=200 °C
Merck 14,6523
BRN 383619
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyDFPAKSUCGFBDDF-UHFFFAOYSA-N
CAS DataBase Reference98-92-0(CAS DataBase Reference)
NIST Chemistry ReferenceNiacinamide(98-92-0)
EPA Substance Registry SystemNicotinamide (98-92-0)
Safety Information
Hazard Codes Xi,T,F
Risk Statements 36/37/38-39/23/24/25-23/24/25-11
Safety Statements 26-36-37/39-45-36/37-16-7
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 1
RTECS QS3675000
8
Autoignition Temperature480 °C
TSCA Yes
HS Code 29362990
Hazardous Substances Data98-92-0(Hazardous Substances Data)
ToxicityLD50 s.c. in rats: 1.68 g/kg (Brazda, Coulson)
MSDS Information
ProviderLanguage
3-Pyridinecarboxamide English
SigmaAldrich English
ACROS English
ALFA English
Nicotinamide Usage And Synthesis
descriptionNicotinamide is also called vitamin B3 or vitamin PP, is a kind of water-soluble vitamin, belong to B vitamin, as NAD (nicotinamide adenine dinucleotide, NAD) and NADP (nicotinamide adenine dinucleotide phosphate, NADP) composition, hydrogenation and dehydrogenation properties of nicotinamide in the body part of this two kinds of structure of coenzyme the reversible, play a role of hydrogen delivery in biological oxidation, can promote tissue respiration, biological oxidation process and the new supersedes the old, having a great significance in maintaining normal tissue, especially the integrity of the skin digestive tract and the nervous system. When the lack of B vitamins, due to respiration and metabolism of cells affected by pellagra, so this product is mainly used for the prevention and treatment of pellagra, stomatitis, glossitis and so on. In addition, this product has prevention of heart block and improving the sinoatrial node and anti-fast experimental arrhythmia function, can significantly improve Vera Pammy induced bradycardia and atrioventricular block. The clinical for coronary heart disease, viral myocarditis, rheumatic heart disease and a handful of digitalis poisoning associated with arrhythmia (mostly applied only when other medications fail), generally the degree atrioventricular block has obvious curative effect, basically after the treatment, all block can disappear, has obvious curative effect in sick sinus syndrome, right bundle branch block effect is poor. After the stomach intestinal absorption by the oral, intramuscular absorption faster, then absorption distribution to the body tissues, t1/2 is 45 min. The liver metabolism, most metabolize N-n-methylnicotinamide, only a small amount of treatment as the prototype from the urine was more than necessary. If the daily urinary excretion of N-methyl nicotinamide is lower than 4mg, suggesting that nicotinamide deficiency.
Nicotinamide and nicotinic acid are collectively referred to vitamin PP, nicotinic acid in the animal body is involved in metabolic processes in the form of nicotinamide, both have a common vitamin activity. It is white crystalline powder, odorless or almost odorless, bitter taste, easily soluble in water or ethanol, soluble in glycerol. Hygroscopic weak stable., acid, alkali and high temperature. The nature mainly exists in cereal skin, yeast, peanuts, meat, animal organs, milk and green leafy vegetables, in the body it is from tryptophan synthesis, but the efficiency is very low. Escherichia coli in the intestine (Escherichia coli) can be converted into synthesis of nicotinic acid, nicotinamide. Prevention and treatment of pellagra, exposed parts of symmetric dermatitis, stomatitis, glossitis, anorexia, dermatitis, liver disease, coronary heart disease, atrioventricular block, sick sinus syndrome, diarrhea, neuritis and dementia.
[Adverse reaction] Occasionally dizziness, nausea, abdominal discomfort, loss of appetite, disappear on their own, in early pregnancy overdose possible teratogenic intramuscular injection can cause pain, so less.
The above information is Chemicalbook Hanya edited.
Chemical PropertiesIt 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 the product 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. Rats by oral LD502.5-3.5g/kg ADI value does not make special provisions (ECC, 1990)
UsesSame as nicotinic acid. Water soluble is better than niacin acid, easy to generate complex agglomerate with vitamin C. The dosage is 30-80 mg/kg.
Nicotinamide and nicotinic acid are in common use generally and nicotinic acid can transform into nicotinamide in animals. Lack of nicotinic acid and nicotinamide, results in pellagra. So they can prevent pellagra. They also play a role in the metabolism of protein and sugar, which can improve human and animal nutrition. In addition to be used as a medicine, it can also be applied in food and feed additives. The production capacity is more than 30000 tons in the world. In Japan, niacinamide used in medicine (40%), feed additives (50%) and food additives (10%). Nicotinic acid and nicotinamide are non-toxic, naturally contains in liver, kidney, yeast and honey. The niacinamide LD50 of subcutaneous injection for rat is 1.7 g/kg.
It is of Vitamin drugs, and involved in metabolic process. Can be used in skin care products, to prevent coarse skin, maintain healthy skin cells, and promote skin whitening. In addition, it can also be used in hair care products, to promote scalp blood circulation, healthy hair follicles, promotes hair growth and prevent alopecia.
Used in biochemical research. To prepare tissue culture medium. The pharmaceutical industry.
ToxicityLD50 2.5~3.5 g/kg (rats, through the mouth).
GRAS(FDA,§182.5535,2000).
ADI is no special regulation (EEC, 1990).
Synthesis1.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.
2.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%.
3. From the nicotinic acid and ammonia react into salt and then dehydrated.
DescriptionA white, crystalline powder. It is odorless or nearly so, and has a bitter taste. Its 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.
Chemical PropertiesNiacinamide is a white crystalline powder or forms colorless needle-like crystals.
OriginatorNiacinamide,Twinlab
UsesA water-soluble vitamin B, incorporated within nicotinamide cofactors such as NADH and NADPH.
UsesVitamin B3; enzyme cofactor; anti-pellagra
UsesNiacinamide USP is used as food additive, for multivitamin preparations and as intermediate for pharmaceuticals and cosmetics.
Usesniacinamide is used as a skin stimulant and skin smoother. It is a derivative of niacin, and part of the vitamin B family.
UsesNiacinamide is a nutrient and dietary supplement that is an available form of niacin. Nicotinic acid is pyridine beta-carboxylic acid and nicotinamide, which is another term for niacinamide, is the corresponding amide. It is a powder of good water solubility, having a solubility of 1 g in 1 ml of water. Unlike niacin, it has a bitter taste; the taste is masked in the encapsulated form. Used in fortification of cereals, snack foods, and powdered beverages.
DefinitionChEBI: A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.
Manufacturing ProcessGaseous 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. obtained. 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.
Therapeutic FunctionEnzyme cofactor vitamin
Synthesis Reference(s)Journal of the American Chemical Society, 76, p. 5774, 1954 DOI: 10.1021/ja01651a043
Tetrahedron Letters, 36, p. 8657, 1995 DOI: 10.1016/0040-4039(95)01785-G
General DescriptionVitamin B3 was formerly called nicotinic acid; however, the term niacin is now preferred to avoid any confusion with the alkaloid, nicotine. Niacinamide, 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.
General DescriptionWhite powder.
Air & Water ReactionsWater soluble.
Reactivity ProfileAn amine and amide. Acts as a weak base in solution. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Clinical UseNiacin 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 niacin. 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. Niacin deficiency can also result from diarrhea, cirrhosis, alcoholism, or Hartnup disease. It is interesting that niacin deficiency can also, rarely, result from vitamin B6 deficiency (see Vitamin B6 section). Niacin, but not niacinamide, is also one of the few vitamins that are useful in the treatment of diseases unrelated to deficiencies.
Safety ProfileModerately toxic by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Potential ExposureUsed as a dietary supplement and food additive.
Purification MethodsCrystallise niacin from *benzene. It has solubility in g/ml: H2O (1), EtOH (0.7) and glycerol (0.1). [Methods in Enzymology 66 23 1980, UV: Armarego Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 83 1971, Beilstein 22 III/IV 389, 22/2 V 80.]
IncompatibilitiesCombustible solid; dust may form explosive mixture with air. Amides are incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
Tag:Nicotinamide(98-92-0) Related Product Information
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