3D Mol Similar

Nicotinic acid

: Iupac Name：pyridine-3-carboxylic acid; CAS No.: 59-67-6; Molecular Weight：123.111; Modify Date.: 2023-02-21 16:37; Introduction: Niacin is an additive to food on the basis of its nutrient supplement qualities as a vitamin (as an enzyme co-factor). This water-soluble vitamin of the B complex occurs in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. A deficiency of niacin results in the disease, pellagra. View more+

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1. Names and Identifiers

: 1.1 Name; Nicotinic acid; 1.2 Synonyms; 3-CARBOXYPYRIDINE 3-PICOLINIC ACID 3-Pyridinecarboxylic acid 3-Pyridylcarboxylic acid 5-22-02-00057 5-22-02-00057 (Beilstein Handbook Reference) ACIDUM-NICOTINICUM AKOS BBS-00003719 antipellagra vitamin BETA-PICOLINIC ACID EINECS 200-441-0 MFCD00006391 Niacin Nicotinamide P. P. Factor P.P. factor-pellagra preventive factor Pyridine-3-carboxylic acid Pyridine-Β-carboxylic acid RARECHEM AL BO 0217 T6NJ CVQ TIMTEC-BB SBB004279 Vitamin B3; View all

1.3 CAS No.: 59-67-6

1.4 CID: 938

1.5 EINECS(EC#): 200-441-0

1.6 Molecular Formula: C6H5NO2 (isomer)

1.7 Inchi: InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)

1.8 InChIkey: PVNIIMVLHYAWGP-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CN=C1)C(=O)O

1.10 Isomers Smiles: C1=CC(=CN=C1)C(=O)O

2. Properties

2.1 Density: 1.473

2.1 Melting point: 234-238℃

2.1 Boiling point: 457° F (NTP, 1992)

2.1 Refractive index: 1.4936

2.1 Flash Point: 193°C c.c.

2.1 Precise Quality: 123.03200

2.1 PSA: 50.19000

2.1 logP: 0.77980

2.1 Solubility: 18g/l

2.2 AnalyticLaboratory Methods: Spectrophotometry for determination of niacin;.

2.3 Appearance: Nicotinic acid is an odorless white crystalline powder with a feebly acid taste. pH (saturated aqueous solution) 2.7. pH (1.3% solution) 3-3.5. (NTP, 1992)

2.4 AutoIgnition: 580°C

2.5 Storage: Ambient temperatures.

2.6 Color/Form: Powder

2.7 Decomposition: When heated to decomposition it emits toxic fumes of nitroxides.

2.8 Odor: Odorless

2.9 PH: pH = 2.7 (saturated aq soln)

2.10 Physical: PHYSICAL DESCRIPTION: Odorless white crystalline powder with a feebly acid taste. pH (saturated aqueous solution) 2.7. pH (1.3% solution) 3-3.5. (NTP, 1992)

2.11 pKa: 4.85(at 25℃)

2.12 Water Solubility: H2O: 1000 g/L (20 oC)

2.13 Spectral Properties: SADTLER REFERENCE NUMBER: 434 (IR, PRISM); 120 (IR, GRATING)
Max absorption: 263 nm
IR: 5076 (Coblentz Society Spectral Collection)
UV: 161 (Sadtler Research Laboratories Prism Collection)
1H NMR: 14671 (Sadtler Research Laboratories Spectral Collection)
MASS: 40521 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 203 (National Bureau of Standards)
Intense mass spectral peaks: 78 m/z, 106 m/z, 137 m/z

2.14 Stability: Stable. Incompatible with strong oxidizing agents. May be light sensitive.

2.15 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.

3.2 General Description: Nicotinic acid, 3-pyridinecarboxylicacid (Niacin), is effective in the treatment of all types ofhyperlipoproteinemia except type I, at doses above thosegiven as a vitamin supplement. The drug reduces VLDLsynthesis and, subsequently, its plasma products, IDL andLDL. Plasma triglyceride levels are reduced because of thedecreased VLDL production. Cholesterol levels are lowered,in turn, because of the decreased rate of LDL formationfrom VLDL. Although niacin is the drug of choicefor type II hyperlipoproteinemias, its use is limited becauseof the vasodilating side effects. Flushing occurs inpractically all patients but generally subsides when thedrug is discontinued.The hypolipidemic effects of niacin may be caused byits ability to inhibit lipolysis (i.e., prevent the release ofFFAs and glycerol from fatty tissues). Therefore, there is areduced reserve of FFA in the liver and diminution oflipoprotein biosynthesis, which reduces the production ofVLDL. The decreased formation of lipoproteins leads to apool of unused cholesterol normally incorporated inVLDL. This excess cholesterol is then excreted throughthe biliary tract.; View all

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 344 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H319 (86.05%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H412 (13.37%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P273, P280, P305+P351+P338, P337+P313, and P501; View all

3.4 History: Huber first synthesized nicotinic acid in 1867. In 1914, Funk isolated nicotinic acid from rice polishings. Goldberger, in 1915, demonstrated that pellagra is a nutritional deficiency. In 1917, Chittenden and Underhill demonstrated that canine blacktongue is similar to pellagra. In 1935, Warburg and Christian showed that niacinamide is essential in hydrogen transport as diphosphopyridine nucleotide (DPN). In the following year, Euler et al. isolated DPN and determined its structure. In 1937, Elvhehjem et al. cured blacktongue by administration of niacinamide derived from liver. In the same year, Fouts et al. cured pellagra with niacinamide. In 1947, Handley and Bond established conversion of tryptophan to niacin by animal tissues.

3.5 Methods of Manufacturing: Preparation by oxidation of alkyl beta-substituted pyridines

3.6 Purification Methods: Crystallise the acid from *benzene, EtOH or H2O. It sublimes without decomposition. [McElvain Org Synth Coll Vol I 385 1941, Beilstein 22 III/IV 439, 22/2 V 57.] Nicotinic acid Preparation Products And Raw materials Raw materials

3.7 Usage: This product is a type of vitamin supplement, and it is called vitamin PP along with nicotinamide. It is used to treat pellagra and as a vasodilator, and it is widely used as an additive for food and feed.A medicine intermediate, used in the production of isoniazid, nicotinamide, nikethamide, inositol nicotinate, etc.Nicotinic acid is an important factor in delivering hydrogen and fighting pellagra in organisms; it helps maintain skin and nerve health and stimulate digestion.Coenzyme and cofactor; pyridine nucleotide coenzyme; decreases the amount of low density lipoproteins in the liver and slows the fibrosis of apolipoproteins.Biochemistry research, a nutritional component of tissue culture mediums.

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 Exposure Standards and Regulations: Substance added directly to human food affirmed as generally recognized as safe (GRAS).
Niacin used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

4.2 Octanol/Water Partition Coefficient: log Kow = 0.36

4.3 Fire Hazard: Flash point data for Nicotinic acid are not available; however, Nicotinic acid is probably combustible.

4.4 Hazard Declaration: H319

4.4 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.5 RIDADR: 25kgs

4.5 Safety Profile: Poison byintraperitoneal route. Moderately toxic byingestion, intravenous, and subcutaneousroutes. Human systemic effects: change inclotting factors, changes in platelet count.Questionable carcinogen with experimentalcarcinogenic data. When heated todecomposition it emits toxic fumes of NOx.

4.6 Caution Statement: P280-P305 + P351 + P338-P337 + P313

4.6 Formulations/Preparations: GRADES: NATIONAL FORMULARY; FOOD CHEMICALS CODEX; BLENDED WITH SOY FLOUR (ANIMAL FEEDS)
Oral: Capsules, extended-release: 125 mg; 250 mg; 400 mg; 500 mg; Tablets: 50 mg 100 mg; 250 mg; 500 mg; (available by nonproprietary name). Tablets, extended-release: 250 mg Slo-Niacin, (Upsher-Smith); 500 mg Slo-Niacin, (Upsher-Smith); 750 mg Slo-Niacin, (Upsher-Smith).
Oral: Tablets, extended-release: 500 mg with Lovastatin 20 mg Advicor ( with povidone), (Kos); 750 mg with Lovastatin 20 mg Advicor ( with povidone), (Kos); 1 g with Lovastatin 20 mg Advicor ( with povidone), (Kos); 1 g with Lovastatin 40 mg Advicor ( with povidone), (Kos). /Niacin combinations/
Oral: Tablets: 500 mg Niacor (scored), (Upsher-Smith). Tablets, extended-release: 500 mg Niaspan, (Kos); 750 mg Niaspan, (Kos); 1000 mg Niaspan, (Kos).

4.7 WGK Germany: 1

4.7 RTECS: QS3675000

4.7 Protective Equipment and Clothing: In the workplace, single or repeated contact can lead to a flush effect on the skin, including the face. The reddening is the result of increased peripheral blood circulation from dilation of capillaires at the skin surface. The flush effect is accompanied by sensations of itching, tingling, and warmness of the skin. It vanishes after the exposure has ended and is thus reversible.

4.8 Reactivities and Incompatibilities: Dust explosion. Avoid contact with strong acids, alkaline solutions and oxidizing agents.

4.9 Report: Reported in EPA TSCA Inventory.

4.10 Skin, Eye, and Respiratory Irritations: In the workplace, single or repeated contact can lead to a flush effect on the skin, including the face. The reddening is the result of increased peripheral blood circulation from dilation of capillaires at the skin surface. The flush effect is accompanied by sensations of itching, tingling, and warmness of the skin. It vanishes after the exposure has ended and is thus reversible.

4.11 Safety: Poison by intraperitoneal route. Moderately toxic by ingestion, intravenous, and subcutaneous routes. Human systemic effects: change in clotting factors, changes in platelet count. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.?
S24/25: Avoid contact with skin and eyes.
WGK Germany of Niacin (CAS NO.59-67-6): 1

4.12 Specification: ?Niacin (CAS NO.59-67-6), its Synonyms are Nicotinic acid ; 3-Pyridinecarboxylic acid ; 3-Carboxypyridine ; Acide nicotinique ; Acido nicotinico ; Acidum nicotinicum ; Akotin ; Apelagrin ; Kyselina nikotinova ; Enduracin ; Daskil ; Davitamon PP ; Diacin ; Direktan ; Niaspan Titration Starter Pack ; Nicacid ; Nicagin ; Nicamin ; Nicangin ; Pyridine-3-carboxylic acid ; Pyridine-beta-carboxylic acid ; Pyridine-carboxylique-3 ; Pyridinecarboxylic acid, 3- . It is odorless white crystalline powder with a feebly acid taste.

4.13 Toxicity: LD50 s.c. in rats: 5 g/kg (Brazda, Coulson)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

ESR : UV IRRAD IN SOLUTION(H2O)

ESR : UV IRRAD. OF NA SALT IN H2O RICH MIXED SOLV.

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

1H NMR : Predict

Predict 1H proton NMR

gas

IR : KBr disc

IR : nujol mull

SOLID (1 mg / 200 mg KBr DISC) VS KBr

SOLID (NUJOL MULL)

Mass

7. Synthesis Route

59-67-6Total: 112 Synthesis Route

85-48-3 42 Suppliers

59-67-6 656 Suppliers

Literatures:
Sidorov, O. F.; Kosareva, M. A. J. Appl. Chem. USSR (Engl. Transl.), 1983 , vol. 56, # 1 p. 227 - 228,219 - 220
Yield: ~90%

89-00-9 297 Suppliers

59-67-6 656 Suppliers

Literatures:
Recueil des Travaux Chimiques des Pays-Bas, , vol. 1, p. 122
Yield: ~%

91-22-5 119 Suppliers

59-67-6 656 Suppliers

Literatures:
Mem. Muroran Univ. Eng., , vol. 3, p. 283,299
Yield: ~%

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8. Other Information

8.0 Usage: Vitamin of the B complex with hypolipidemic properties occurring in various animal and plant tissues. Required by the body for the formation of coenzymes NAD and NADP.Nicotinic acid is used as an antidyslipidemic agent. It is also used to improve all lipoproteins well above the vitamin requirement and lowers the total cholesterol, "bad" LDL-cholesterol, and triglyceride levels. Further, it is used as a food additive in food industries, cosmetics and pharmaceuticals. In addition to this, it is used in medication, nutrient, enriched flours and in electroplating baths.

8.1 Merck: 14,6525

8.2 BRN: 109591

8.3 Chemical Properties: Nicotinic acid, also known as niacin or vitamin B3, is a white crystal or crystalline powder, odorless or has a slight odor, slight sour taste. Melting point is 234-237℃. Easily soluble in hot water, hot ethanol, alkaline water, propylene glycol, and chloroform. Slightly soluble in water and ethanol; 100ml room temperature water can dissolve 1.6g. Insoluble in ether and ester solutions. The PH of 1% aqueous solution is 3.0-4.0. Stable in heat, acidity and alkalinity.
Nicotinic acid can produce a variety of adverse effects, depending on the intake and health of the consumer. The skin flushing reaction produced by nicotinic acid has been recognized for more than 70 years (Bean 1978). When taken on an empty stomach, crystalline nicotinic acid in doses as small as 10 mg may produce a mild and transient, but noticeable, flushing reaction. While not desirable, such reactions produce no known adverse consequences, and they are almost never perceptible when small amounts of nicotinic acid are taken in tablet or capsule form or consumed as part of food.; View all

8.4 Uses: Nicotinic acid is an important factor in delivering hydrogen and fighting pellagra in organisms; it helps maintain skin and nerve health and stimulate digestion.
Nicotinic acid or niacinamide are used to treat and prevent pellagra. This is a disease caused by niacin deficiency. Niacin is also used to treat high cholesterol. In some cases, niacin taken with colestipol can work as well as colestipol and a statin medicine.
Niacin USP granular is used for food fortification, as dietary supplement and as an intermediate of pharmaceuticals.
Niacin feed grade is used as vitamin for poultry, swines, ruminants, fish, dogs and cats, etc. It is also used as intermediate for nicotinic acid derivatives and technical applications.

8.5 Preparation

Nicotinic acid exists naturally in grain germs, meats and peanuts. It can also be synthesized artificially through the liquid phase method (potassium permanganate oxidation and nitric acid oxidation) and gas phase method (ozone oxidation, ammonia oxidation and air oxidation).

3-methyl pyridine method

In the gas phase ammonia oxidation process, add 3-methyl pyridine, air and ammonia into the fluidized bed reactor and catalyze the reaction at 290～360℃,V2O5 to produce nicotinonitrile; then hydrolyze in sodium hydroxide aqueous solution at 160℃ to produce sodium nicotinate; finally, add hydrochloric acid to acidify, creating nicotinic acid. In the potassium permanganate oxidation method, add potassium permanganate gradually at 80℃ to a mixture of 3-methyl pyridine and water, and then continue to mix for 30min at 85～90℃. Distill to collect and reuse the unreacted 3-methyl pyridine and filter away the produced manganese dioxide. Adjust the PH of the resulting nicotinic acid solution to 3.8～4.0 using hydrochloric acid, cool to 30℃ crystals, and filter to obtain crude nicotinic acid. Dissolve the crude nicotinic acid in hot water, add activated charcoal to eliminate the color, filter, cool, and obtain the crystalline end product. Yield is approximately 86%.

6- hydroxyquinoline method

Add sulfuric acid and quinoline into a reaction kettle and mix while maintaining heat at 150～160℃ for 5h. Then with the temperature maintained at 180～220℃, slowly drop in nitric acid and the sulfuric acid mixture over the course of 36～40h. While maintaining the temperature, mix for 2～3h to obtain a nicotinic acid solution and add water to dilute the solution. Use 30％～33％ NaOH solution to neutralize the PH to 8～9. Cool and filter away the sodium sulfate and sodium nitrate crystals, add copper sulfate solution to the filtered liquid, and mix and heat to yield copper nicotinate precipitation. Cool, filter and add the copper nicotinate to an adequate amount of water, drop in NaOH solution until PH>9 and the liquid is no longer blue, and filter away the produced cupric oxide. Add a small amount of sodium sulfide solution to remove traces of copper and iron until the solution no longer produces black precipitate, and then filter. Use hydrochloric acid to adjust the PH of the filtered liquid to 3.5～3.9, filter to yield crystals as crude nicotinic acid. Dissolve the crude product in 12 times the amount of distilled water, add activated charcoal to eliminate the color, filter, cool, and obtain the crystalline end product. Yield is 35％～39％.

2-methyl-5-ethyl pyridine method

With 2-methyl-5-ethyl pyridine as the raw ingredient, oxidize with nitic acid under high pressure and high temperatures, then decarboxylate to yield nicotinic acid.

View all

8.6 Identifying tests: Add 2 portions of 2, 4-Dinitrochlorobenzene to the sample and process into powder. Place 10mg of the powder in a test tube, gently heat until melted, and continue to heat for a couple of seconds. Cool and add 3ml potassium hydroxide ethanol solution (TS-190). The solution should be dark red.
Dissolve 50mg of the sample solution in 20ml water, use 0.1mol/L sodium hydroxide to neutralize until a litmus paper reads neutral, and add 3ml copper sulfate solution (TS-78). Blue precipitate should begin forming slowly.
Dry the sample for 1h at 105℃ and collect its mineral oil dispersions. The peak wavelength of its infrared absorption spectrum should resemble the standard reference sample formulated using the same method.
Prepare an aqueous solution of the sample with a density of 20μg/ml, measure its absorbance at the wavelengths 237nm and 262nm in a 1cm pool, using water as a blank control. A237/A262 should be 0.35～0.39.

8.7 Content analysis: Precisely take a sample of 300mg and dissolve in 50ml water. Add a couple drops of phenolphthalein solution (TS-167) and titrate using 0.1mol/L sodium hydroxide. Conduct a control experiment at the same time. Every Ml0.1mol/L sodium hydroxide is equivalent to 12.31mg nicotinic acid (C6H5NO2).

8.8 Toxicity: LD50 7.0g/kg (Large mice, oral).
GRAS(FDA，§182.5530，2000)。
ADI has no special regulations (EEC, 1990).

8.9 Description: Niacin is an additive to food on the basis of its nutrient supplement qualities as a vitamin (as an enzyme co-factor). This water-soluble vitamin of the B complex occurs in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. A deficiency of niacin results in the disease, pellagra.

8.10 Chemical Properties: NIACIN is sometimes referred to as nicotinic acid or nicotinamide and earlier called the P-P factor, antipellagra factor, antiblacktongue factor, and vitamin B4, niacin is available in several forms (niacin, niacinamide, niacinamide ascorbate, etc.) for use as a nutrient and dietary supplement. Niacin is frequently identified with the B complex vitamin grouping. Early in the research on niacin, a nutritional niacin deficiency was identified as the cause of pellagra in humans, blacktongue in dogs, and certain forms of dermatosis in humans. Niacin deficiency is also associated with perosis in chickens as well as poor feathering of the birds.

8.11 Physical properties: Nicotinic acid and nicotinamide are colorless crystalline substances. Each is insol uble or only sparingly soluble in organic solvents. Nicotinic acid is slightly soluble in water and ethanol; nicotinamide is very soluble in water and moderately soluble in ethanol
Nicotinic acid is amphoteric and forms salts with acids as well as bases. Its car boxyl group can form esters and anhydrides and can be reduced. Both nicotinic acid and nicotinamide are very stable in dry form, but in solution nicotinamide is hydro lyzed by acids and bases to yield nicotinic ac
The coenzyme forms of niacin are the pyridine nucleotides, NAD(H) and NADP(H). In each of these compounds, the electron-withdrawing effect of the N-1 atom and the amide group of the oxidized pyridine nucleus enables the pyridine C-4 atom to react with many nucleophilic agents (e.g., sulfite, cyanide, and hydride ions). It is the reaction with hydride ions (H?) that is the basis of the enzymatic hydrogen transfer by the pyridine nucleotides; the reaction involves the transfer of two electrons in a single step
Several substituted pyridines are antagonists of niacin in biological systems: pyridine-3-sulfonic acid, 3-acetylpyridine, isonicotinic acid hydrazine, 17 and 6-aminonicotinamide; View all

8.12 History: Huber first synthesized nicotinic acid in 1867. In 1914, Funk isolated nicotinic acid from rice polishings. Goldberger, in 1915, demonstrated that pellagra is a nutritional deficiency. In 1917, Chittenden and Underhill demonstrated that canine blacktongue is similar to pellagra. In 1935, Warburg and Christian showed that niacinamide is essential in hydrogen transport as diphosphopyridine nucleotide (DPN). In the following year, Euler et al. isolated DPN and determined its structure. In 1937, Elvhehjem et al. cured blacktongue by administration of niacinamide derived from liver. In the same year, Fouts et al. cured pellagra with niacinamide. In 1947, Handley and Bond established conversion of tryptophan to niacin by animal tissues.

8.13 Uses: niacin is also known as vitamin B3. It is a water-soluble conditioning agent that improves rough, dry, or flaky skin, helping smooth the skin and improve its suppleness. niacin enhances the appearance and feel of hair, by increasing body, suppleness, or sheen, or by improving the texture of hair that has been damaged physically or by chemical treatment. When used in the formulation of skin care products, niacinamide and niacin enhance the appearance of dry or damaged skin by reducing flaking and restoring suppleness.

8.14 Uses: Nicotinic acid. It is a precursor of the coenzymes NAD and NADP. 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.
Niacin is a water-soluble b-complex vitamin that is necessary for the growth and health of tissues. It prevents pellagra. It has a solubility of 1 g in 60 ml of water and is readily soluble in boiling water. It is relatively stable in storage and no loss occurs in ordinary cooking. Sources include liver, peas, and fish. It was originally termed nicotinic acid and also functions as a nutrient and dietary supplement.

8.15 Uses: Nicotinic acid. It is a precursor of the coenzymes NAD and NADP. 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 or to other derivatives exhibiting the biological activity of nicotinic acid. Vitamin (enzyme cofactor).

8.16 Definition: ChEBI: A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.

8.17 Brand name: Niacor (Upsher Smith); Niaspan (KOS); Nicolar (Sanofi Aventis); Wampocap (Medpointe).

8.18 General Description: Odorless white crystalline powder with a feebly acid taste. pH (saturated aqueous solution) 2.7. pH (1.3% solution) 3-3.5.

8.19 General Description: Nicotinic acid, 3-pyridinecarboxylicacid (Niacin), is effective in the treatment of all types ofhyperlipoproteinemia except type I, at doses above thosegiven as a vitamin supplement. The drug reduces VLDLsynthesis and, subsequently, its plasma products, IDL andLDL. Plasma triglyceride levels are reduced because of thedecreased VLDL production. Cholesterol levels are lowered,in turn, because of the decreased rate of LDL formationfrom VLDL. Although niacin is the drug of choicefor type II hyperlipoproteinemias, its use is limited becauseof the vasodilating side effects. Flushing occurs inpractically all patients but generally subsides when thedrug is discontinued.
The hypolipidemic effects of niacin may be caused byits ability to inhibit lipolysis (i.e., prevent the release ofFFAs and glycerol from fatty tissues). Therefore, there is areduced reserve of FFA in the liver and diminution oflipoprotein biosynthesis, which reduces the production ofVLDL. The decreased formation of lipoproteins leads to apool of unused cholesterol normally incorporated inVLDL. This excess cholesterol is then excreted throughthe biliary tract.; View all

8.20 Air & Water Reactions: Water soluble.

8.21 Reactivity Profile: Nicotinic acid is incompatible with strong oxidizers. Nicotinic acid is also incompatible with sodium nitrite.

8.22 Fire Hazard: Flash point data for Nicotinic acid are not available; however, Nicotinic acid is probably combustible.

8.23 Biological Activity: Nicotinic acid can be converted to nicotinamide in the animal body and, in this form, is found as a component of two oxidation-reduction coenzymes, NAD and NADP.The nicotinamide portion of the coenzyme transfers hydrogens by alternating between an oxidized quaternary nitrogen and a reduced tertiary nitrogen. Enzymes that contain NAD or NADP are usually called dehydrogenases. They participate in many biochemical reactions of lipid, carbohydrate, and protein metabolism. An example of an NAD-requiring system is lactic dehydrogenase which catalyzes the conversion of lactic acid to pyruvic acid.

8.24 Biochem/physiol Actions: Nicotinic is an antioxidant and acts as a coenzyme in the form of nicotinamide adenine nucleotides(NAD). It modulates lipid metabolism and may be useful in treating dyslipidemia. Nicotinic acid reduces the low-density lipoprotein (LDL) synthesis and improves high-density lipoprotein (HDL) levels. Deficiency of niacin leads to enhanced lipid peroxidation and is implicated in Crohn′s disease Deficiency also impacts DNA repair and also leads to skin and gastrointestinal disorder pellagra.

8.25 Mechanism of action: Nicotinic acid decreases formation and secretion of VLDL by the liver.This action appears secondary to its ability to inhibit fatty acid mobilization from adipose tissue. Circulating free fatty acids provide the main source of fatty acids for hepatic triglyceride synthesis, and lowering triglyceride synthesis lowers VLDL formation and secretion by the liver. Since plasma VLDL is the source of LDL, lowering VLDL can ultimately lower LDL. In addition, nicotinic acid shifts LDL particles to larger (more buoyant) sizes. The larger LDL particles are thought to be less atherogenic. Nicotinic acid can also significantly increase plasma HDL levels; the mechanism is unknown.

8.26 Pharmacokinetics: Nicotinic acid is readily absorbed. Peripheral vasodilation is seen within 20 minutes, and peak plasma concentrations occur within 45 minutes. The half-life of the compound is approximately one hour, thus necessitating frequent dosing or an extended-release formulation. Extended release tablets produce peripheral vasodilation within 1 hour, reach peak plasma concentrations within 4 to 5 hours, and have a duration of 8 to 10 hours.
Dosing of nicotinic acid should be titrated to minimize adverse effects. An initial dose of 50 to 100 mg t.i.d. often is used with immediaterelease tablets. The dose then is gradually increased by 50 to 100 mg every 3 to 14 days, up to a maximum of 6 g/day, as tolerated. Therapeutic monitoring to assess efficacy and prevent toxicity is essential until a stable and effective dose is reached. Similar dosing escalations are available for extended-release products, with doses normally starting at 500 mg once daily at bedtime..

8.27 Clinical Use: Nicotinic acid has been esterified to prolong itshypolipidemic effect. Pentaerythritol tetranicotinate hasbeen more effective experimentally than niacin in reducingcholesterol levels in rabbits. Sorbitol and myo-inositolhexanicotinate polyesters have been used in the treatment ofpatients with atherosclerosis obliterans.The usual maintenance dose of niacin is 3 to 6 g/daygiven in three divided doses. The drug is usually given atmealtimes to reduce the gastric irritation that often accompanieslarge doses.

8.28 Side effects: Compliance with nicotinic acid therapy can be poor because the drug can produce an intense cutaneous flush. This can be reduced by beginning the drug in stepped doses of 250 mg twice daily and increasing the dose monthly by 500 to 1000 mg per day to a maximum of 3000 mg per day.Taking nicotinic acid on a full stomach (end of meal) and taking aspirin before dosage can reduce the severity of flushing. Time-release forms of nicotinic acid may also decrease cutaneous flushing. Nicotinic acid can cause gastrointestinal (GI) distress，liver dysfunction (especially at high doses), decreased glucose tolerance, hyperglycemia, and hyperuricemia. Thus, it is contraindicated in patients with hepatic dysfunction, peptic ulcer, hyperuricemia, or diabetes mellitus. A paradox associated with nicotinic acid is that it is the most widely available hypolipidemic drug (it is sold over the counter), yet its use requires the closest management by the physician.

8.29 Safety Profile: Poison by intraperitoneal route. Moderately toxic by ingestion, intravenous, and subcutaneous routes. Human systemic effects: change in clotting factors, changes in platelet count. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx.

8.30 Chemical Synthesis: Nicotinic acid, pyridine-3-carboxylic acid (20.2.9) is synthesized industrially by heating a paraldehyde trimer of acetaldehyde, under pressure with ammonia, which leads to the formation of 2-methyl-5-ethylpyridine, followed by oxidation with nitric acid which gives the desired product.

8.31 Metabolism: Nicotinic acid is a B-complex vitamin that is converted to nicotinamide, NAD+ , and NADP+ .The latter two compounds are coenzymes and are required for oxidation/reduction reactions in a variety of biochemical pathways. Additionally, nicotinic acid is metabolized to a number of inactive compounds, including nicotinuric acid and N-methylated derivatives. Normal biochemical regulation and feedback prevent large doses of nicotinic acid from producing excess quantities of NAD+ and NADP+ .Thus, small doses of nicotinic acid, such as those used for dietary supplementation, will be primarily excreted as metabolites, whereas large doses, such as those used for the treatment of hyperlipoproteinemia, will be primarily excreted unchanged by the kidney.

8.32 Purification Methods: Crystallise the acid from *benzene, EtOH or H2O. It sublimes without decomposition. [McElvain Org Synth Coll Vol I 385 1941, Beilstein 22 III/IV 439, 22/2 V 57.]

8.33 Storage features: Store in an area without drain or sewer access. Separated from strong acids, bases and oxidants.

9. Computational chemical data

Molecular Weight: 123.111g/mol
Molecular Formula: C₆H₅NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 123.032028402
Monoisotopic Mass: 123.032028402
Complexity: 114
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 50.2
Heavy Atom Count: 9
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBiMAAAAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgAACAAADADBmgQ8iJIIEgCoAjD3TACCgCA1AiAI2CE4bNgIJvrAlZGEcYhmwAHI2caYEQIMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What is the mechanism of action of Nicotinic Acid? Jul 05 2024
Introduction: Nicotinic Acid, as a member of vitamin B3 family, is known for its many important biological functions. It participates in a variety of key metabolic channels in the human body, includi..
What are the benefits of nicotinic acid in health and wellness? Jul 05 2024
Introduction: Nicotinic Acid, or vitamin B3, is a nutrient that is vital to human health. It plays a key role in energy metabolism, cell repair and nervous system functions. Although Nicotinic Acid c..
What is the role of Nicotinic Acid in the body? Jul 05 2024
Introduction: Nicotinic Acid, also known as vitamin B3, is one of the important nutrients required by the human body. It plays a variety of key role in the body, including the regulation of energy me..
What are the Mechanisms and Effects of Nicotinic Acid on Lipid Profile and Cardiovascular Risk? May 14 2024
General Description Nicotinic acid, also known as niacin, impacts lipid profile and cardiovascular risk through various mechanisms. It reduces triglycerides and LDL cholesterol levels while increasing..

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