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Nicotinamide(CAS No. 98-92-0)

Nicotinamide C6H6N2O (cas 98-92-0) Molecular Structure

98-92-0 Structure

Identification and Related Records

【Name】
Nicotinamide
【CAS Registry number】
98-92-0
【Synonyms】
Pyridine-3-carboxamide
niacinamide cell culture tested
Nicotinamide (1.06818)
Niacinamide
Vitamin PP
VB3
VPP
Pyridine-3-Carboxyamide
3-Pyridinecarboxyamide
Vitamin B3
Nicotinic acid amide
【EINECS(EC#)】
202-713-4
【Molecular Formula】
C6H6N2O (Products with the same molecular formula)
【Molecular Weight】
122.13
【Inchi】
InChI=1/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)
【InChIKey】
DFPAKSUCGFBDDF-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC(=CN=C1)C(=O)N
【MOL File】
98-92-0.mol

Chemical and Physical Properties

【Appearance】
White to off white powder
【Density】
1.204g/cm3
【Melting Point】
128-131℃
【Boiling Point】
150-160℃
【Refractive Index】
1.466 (20 C)
【Flash Point】
182℃
【Water】
1000 g/L (20℃)
【Solubilities】
Incompatible with strong oxidizing agents
【Color/Form】
white
【Stability】
Stable. Incompatible with strong oxidizing agents.
【HS Code】
29362990
【Storage temp】
0-6°C
【Spectral properties】
MAX ABSORPTION (ALCOHOL): 255 NM (LOG E= 3.4); 262.5 NM (LOG E= 3.4); INDEX OF REFRACTION: 1.466; SADTLER REFERENCE NUMBER: 860 (IR, PRISM); 8106 (IR, GRATING)
Index of refraction: 1.466
IR: 5080 (Coblentz Society Spectral Collection)
UV: 261 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 453 (Varian Associates NMR Spectra Catalogue)
13C NMR: 259 (Johnson and Jankowski, Carbon-13 NMR for Organic Chemists, John Wiley & Sons, New York)
MASS: 2279 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
Raman: 518 (Sadtler Research Laboratories spectral collection)
Intense mass spectral peaks: 78 m/z, 106 m/z, 122 m/z
【Computed Properties】
Molecular Weight:122.12464 [g/mol]
Molecular Formula:C6H6N2O
XLogP3:-0.4
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:1
Tautomer Count:2
Exact Mass:122.048013
MonoIsotopic Mass:122.048013
Topological Polar Surface Area:56
Heavy Atom Count:9
Formal Charge:0
Complexity:114
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Ring Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S36
【Safety】

Hazard Codes: Xi
Risk Statements: 36/37/38:?Irritating to eyes, respiratory system and skin?
Safety Statements: 26-36-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:?Wear suitable protective clothing
37/39: Wear suitable gloves and eye/face protection.
Nicotinamide rarely causes side effects, and is considered generally safe as a food additive, and as a component in cosmetics and medication.
?

【Cleanup Methods】
Evacuate persons not wearing protective equipment from area of spill or leak until clean up is complete. Remove all ignition sources. Use HEPA vacuum or wet method to reduce dust during cleanup. Do not dry sweep. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate after clean up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material of contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or regional office of the federal EPA for specific recommendations. If employees are expected to clean up spills, they must be trained and equipped. OSHA 1910.120 may be applicable.
【Transport】
25kgs
【Fire Fighting Procedures】
This chemical is a noncombustible solid. Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. Poisonous gases are produced in fire. If material of contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increase in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.
【Formulations/Preparations】
Oral: Tablets: 50 mg; 100 mg; 500 mg. (available by nonproprietary name).
Nicotinamide is sold in three grades: pharmaceutical (USP, NF, Ph. Eur.(European Pharmacopeia)), food (USP/FCC), and feed-technical.
【Exposure Standards and Regulations】
Niacinamide 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.
【Specification】

?Nicotinamide , with CAS number of 98-92-0, can be called Niamide ; Niacinamide/Nicotinamide ; Austrovit PP ; beta.-Pyridinecarboxamide ; Nikotinsaeureamid ; Amid kyseliny nikotinove ; Nicotinamidum ; Pyridine-3-carboxylic acid amide ; Nikotinsaeureamid ; Nicotinamide(Vitamin B3) ; a-Alanine,N-[(2R)-2,4-dihydroxy-3,3- dimethyl-1-oxobutyl]- ; 3-Pyridinecarboxamide ; Nicotinamida ; Niacinamide ; 3-Pyridinecarboxylic acid amide ; Nicotine acid amide . Nicotinamide, also known as niacinamide and Nicotinic acid amide, is the amide of Nicotinic acid (vitamin B3). It is a water-soluble vitamin and is part of the vitamin B group.Nicotinic acid(also known as niacin)can be converte to niacinamide in vivo.?It is a?white to off white powder.

【Octanol/Water Partition Coefficient】
log Kow = -0.37
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

NICOTINAMIDE IS USUALLY PREPARED BY ESTERIFYING NICOTINIC ACID WITH METHANOL FOLLOWED BY AMMONOLYSIS.
Preparation from 3-cyanopyridine: E.J.Gasson, D.J. Hadley, US 2904552 (1959 to Distillers). Alternately prepared by passing ammonia gas into molten nicotinic acid: A. Truchan, J.B. Davidson, US 2993051 (1961 to Cowles Chem.).
Nicotinamide is available either from the amidation of nicotinic acid or from partial hydrolysis of 3-cyanopyridine.
Industrial production of nicotinic acid and nicotinamide are based on the raw materials 5-ethyl-2-methylpyridine and 3-methylpyridine (3-picoline).
Ammoxidation of 3-methylpyridine is carried out on a commercial scale in the gas phase using heterogeneous catalysts; oxides of antimony, vanadium, and titanium, or antimony, vanadium, and uranium are highly effective. With an antimony-vanadium-titanium catalyst, a reactor temperature of 360 deg C, and a molar feed ratio of 3-methylpyridine:NH3:air:water vapor of 1:6:30:6, a 96% conversion and a 93% yield of nicotinonitrile were obtained. The nitrile is then hydrolyzed to nicotinamide.
U.S. Imports

(1972) 1.45X10+9 GRAMS
(1975) 7.5X10+7 GRAMS (NICOTINAMIDE ONLY)
In 1980, 297.1 tons of nicotinamide were imported.
U.S. Production

(1972) 2.49X10+9 GRAMS (NIACIN & NICOTINAMIDE)
(1975) 2.5X10+9 GRAMS (NIACIN & NICOTINAMIDE)
Consumption Patterns

APPROX 80% BY ITSELF AS AN ESSENTIAL B VITAMIN; APPROX 20% AS AN ESSENTIAL B VITAMIN IN OTHER APPLICATIONS SUCH AS FLOUR, BAKED GOODS & CEREAL PRODUCTS, & PHARMACEUTICALS (1973)
【Usage】

Niacinamide USP is used as food additive, for multivitamin preparations and as intermediate for pharmaceuticals and cosmetics. WWW Link

Biomedical Effects and Toxicity

【Pharmacological Action】
- A group of water-soluble vitamins, some of which are COENZYMES.
【Therapeutic Uses】
Nicotinamide is used to prevent the neurologic and endocrinologic toxicity associated with the ingestion of Vacor (PNU), a rodenticide that is believed to act by antagonizing nicotinamide. The best results are achieved when nicotinamide therapy is instituted within 3 hours of ingestion. It may also be effective for treatment of Vacor analogs such as alloxan and streptozocin.
Niacin and niacinamide are used to prevent niacin deficiency and to treat pellagra. Some clinicians prefer niacinamide for the treatment of pellagra because it lacks vasodilating effects. Pellagra may result from dietary deficiency, isoniazid therapy, or from decreased conversion of tryptophan to niacin in Hartnup disease or carcinoid tumors.
EXPTL: Although niacin and niacinamide have not been shown by well-controlled trials to have therapeutic value, the drugs have been used for the management of schizophrenic disorder, drug-induced hallucinations, chronic brain syndrome, hyperkinesis, unipolar depression, motion sickness, alcohol dependence, livedoid vasculitis, acne, and leprosy.
Niacin and niacinamide are indicated for prevention and treatment of vitamin B3 deficiency states. Vitamin B3 deficiency may occur as a result of inadequate nutrition or intestinal malabsorption but does not occur in healthy individuals receiving an adequate balanced diet. Simple nutritional deficiency of individual B vitamins is rare since dietary inadequacy usually results in multiple deficiencies. ... /Included in US product labeling/
MEDICATION (VET): As buffer for chloramphenicol preparation.
EXPL: Nicotinamide (vitamin B3) is a weak poly(ADP-ribose) polymerase inhibitor, antioxidant, and calcium modulator and can improve energy status and inhibit cell death in ischemic tissues. /The authors/ report the dose-dependent effects of nicotinamide in an established model of early diabetic peripheral neuropathy. Control and streptozotocin-diabetic rats were treated with 200 to 400 mg/kg/day nicotinamide (ip) for 2 weeks after 2 weeks of untreated diabetes. Sciatic endoneurial nutritive blood flow was measured by microelectrode polarography and hydrogen clearance, and sciatic motor and hind-limb digital sensory nerve conduction velocities and thermal and mechanical algesia were measured by standard electrophysiological and behavioral tests. Malondialdehyde plus 4-hydroxyalkenal concentration in the sciatic nerve and amino acid-(4)-hydroxynonenal adduct and poly(ADP-ribosyl)ated protein expression in human Schwann cells were assessed by a colorimetric method with N-methyl-2-phenyl indole and Western blot analysis, respectively. Nicotinamide corrected increased sciatic nerve lipid peroxidation in concert with nerve perfusion deficits and dose-dependently attenuated nerve conduction slowing, as well as mechanical and thermal hyperalgesia. Nicotinamide (25 mM) prevented high (30 mM) glucose-induced overexpression of amino acid-(4)-hydroxynonenal adducts and poly(ADP-ribosyl)ated proteins in human Schwann cells. In conclusion, /according to the authors/ nicotinamide deserves consideration as an attractive, nontoxic therapy for the treatment of diabetic peripheral neuropathy. [Stevens MJ et al; J Pharmacol Exp Ther 320 (1): 458-64 (2007)]
【Biomedical Effects and Toxicity】
14(C)Niacinamide was incorporated into an oil-in-water (o/w) skin cream and into a 30% (w/w) soap base and applied to the skin of female Colworth Wistar rats. The final concentration of niacinamide in the soap solution was approximately 0.3% (w/v) and was 1% (w/w) in the skin cream. Application of the skin cream and soap paste was made to rat skin at approximately 20 mg/sq cm. The cream was carefully massaged over 10 sq cm of skin for up to 5 min before covering with polythene-lined occlusive protective patches. The rats were placed in metabolism cages for 48 hr during which time all excreta was collected. At 48 hr, the animals were killed and the patch, carcass, and treated area of skin were assayed for 14(C). Up to 32% 14(C) was recovered in excreta and in the carcasses from rats treated with skin cream containing 14(C)Niacinamide and up to 30% from those treated with soap paste.
...Nicotinamide...readily absorbed from all portions of intestinal tract and from parenteral sites of administration. Vitamin is distributed in all tissues.
Niacinamide is widely distributed into body tissues.
Niacin and niacinamide are readily absorbed from the GI tract following oral administration, and niacinamide (no longer commercially available in the US) is readily absorbed from subcutaneous and IM injection sites.
Niacinamide is actively transported to the fetus. Higher concentrations are found in the fetus and newborn, rather than in the mother.
In a group of patients with superficial recurrent or metastatic cancer, plasma nicotinamide levels were dose dependent, showing a maximum 30 minutes after oral treatment with 3 and 6 g (Cmax 0.9-1.0 umol/mL and 0.6-2.2 umol/mL, respectively). Plasma levels dropped quickly in three hours after treatment. At 10 g the maximum plasma level (0.9-2.2 umol/mL) was reached after 2-4 hours and afterwards the decrease was more gradually compared to the lower dose levels (with a plateau phase).
In human volunteers (n=6) given a single dose of nicotinamide (3-9 g) as a tablet or in a liquid form plasma peak concentration (Cmax) was between 0.3 and 1.7 umol/mL and was reached after 0.5-3.0 hours (Tmax). Similar values were found in patients who received 80mg/kg bw nicotinamide during radiotherapy for 12 consecutive days (Tmax = 0.8-4 hr; Cmax = 0.5-1.4 umol/mL; T1/2 = 7.1 hr). In patients, that received nicotinamide daily (oral administration of 80 mg/kg bw/day during 5-7 weeks) a Cmax of > 0.7 umol/mL was found. Maximum plasma concentrations were reached within 0.25-3 hours after administration
Niacin includes two vitamers nicotinic acid and nicotinamide. Humans are able to synthesize nicotinic acid from tryptophan. Another source for nicotinic acid is the gut flora. In humans there is no deamidation of nicotinamide to nicotinic acid in the gut. Nicotinamide is rapidly absorbed in stomach and small intestine. In plasma both the acid and the amide form are found. Erythrocytes take up the acid by a sodiumdependent saturable transport system. Both the acid and the amide are able to pass the blood-brain barrier, however separate systems for uptake have been identified. Brain cells have a high affinity for nicotinamide, but not for nicotinic acid. Nicotinamide is the main substance that is transported between the different tissues as a precursor of NAD synthesis. The liver, kidneys, brain and erythrocytes prefer nicotinic acid as a precursor for NAD synthesis, but testes and ovaries prefer nicotinamide. NAD nucleosidase cleaves NAD with nicotinamide as one of the products. This can be deamidated to form nicotinic acid (and re-converted to NAD) or methylated and released via urine. Excretion of the amide (and its metabolites) tends to be more extensively compared to the acid.
Doses of 1000 mg/kg /of nacinamide/ were given to rabbits ip and orally, doses of 2000 mg/kg were given to rabbits orally. Doses of 500 mg/kg iv were given to cats and dogs. Rats were dosed at 750 mg/kg sc and 1000 mg/kg ip. The blood concentration of niacinamide in cats and dogs was high initially and decreased linearly over several hours. The blood concentration of niacinamide in rabbits increased over several hours and plateaued. No data were given for the rats. /It was/ concluded that niacinamide is rapidly absorbed and distributed throughout the extracellular fluid.
The in vitro absorption of niacinamide from a wide variety of complex matrices was investigated using split thickness human cadaver skin. Non-occluded topical doses of Niacinamide (2-20%), dissolved in various product types including moisturizers, foundations and lipsticks, were applied to skin explants and the rate of penetration was measured for up to 48 hr. ... The rate of penetration was found to be inversely associated with the dose, although the absolute amount of niacinamide transported across the skin increased with starting concentration of niacinamide. At 24 hr, approximately 1.3% of the starting dose was measured in the receptor fluid after application of an oil/water emulsion containing niacinamide. At 48 hr, approximately 10% and 6% niacinamide was absorbed from formula containing 2% and 10%, respectively. In addition, these studies found that the rate of penetration of Niacinamide was relatively independent of the vehicle
Niacinamide was dissolved in acetone and applied at a dose of 4 g/sq cm. The absorption of niacinamide into the receptor fluid at 24 hr was calculated to be 28.8% of the starting dose. Buccal absorption was studied by a method involving circulation of a pre-incubated buffered solution of niacin and niacinamide in the human mouth for 5 min. The samples were analyzed by spectrophotometry. Buccal absorption rates were linear with respect to initial concentration between 2 and 10 mM.
/It was/ reported that 11.08% of the total applied dose of Niacinamide was absorbed after application to the ventral forearm of humans over 5 days (approximately 2-3% of the dose of Niacinamide absorbed per day). In this experiment, 14(C)-labeled niacinamide was dissolved in acetone and applied to a 13 sq cm area of skin, i.e., 4 ug/sq cm. The area was washed 24 hr after application and this procedure was repeated for 4 consecutive days. Urine was collected for 5 days and the concentration of (14)C-labeled Niacinamide was determined. The results were corrected for extra-renal excretion which was determined in a separate experiment in which an intravenous dose of niacinamide (4 ug/sq cm) was administered and the fraction excreted in urine was calculated. The results of these studies demonstrate that niacinamide absorption continues for up to 5 days after topical application, with the maximum absorption rate occurring between 48 hr and 72 hr.
Pregnant JCL:ICR mice received a single intraperitoneal injection of 0.18 uCi of (carbonyl-14(C))Niacinamide/g of bw on day 9 of gestation. Mice were killed 0.5, 1, 3, 6, or 12 hr after injection. Radioactivity was detected in the maternal organs, placenta, and fetus shortly after injection, and decreased gradually. The time to reduce the radioactivity in each organ by a factor of two was approximately 6 hr. However, there were large differences in the radioactivity in each organ. Levels of radioactivity in the placenta and fetus were about 16 and 5 times higher than in the maternal blood, respectively. Small amounts of nicotinamide adenine dinucleotide (NAD+) were detected in the placenta and fetus shortly after injection. Nicotinamide adenine dinucleotide phosphate (NADP-) was mainly found in the liver at 12 hr after injection. Niacin was not detected.
... Male C3H mice /were/ administered aqueous solutions of 13N-Niacinamide via tail vein injections. 13(N)-Niacinamide is transported throughout the body, mainly by simple diffusion, where part of the tracer is metabolized into hydrophilic compounds, i.e., 13N-NAD, etc., and trapped. Most radioactivity was found in the small intestine, where the level continuously increased for 30 min after administration, despite a rapidly decreasing blood level.
When large doses (500 mg/kg bw) of niacin or niacinamide were given by intraperitoneal injection to female Sprague-Dawley rats, the compounds were excreted largely unchanged in the urine. However, at low doses (5 mg/kg bw), N1-methylnicotinamide was the main excretory product of niacinamide. Small amounts of niacinamide and pyridone derivatives were also excreted. In case of injected niacin, about equal amounts of N1-methylnicotinamide and nicotinuric acid were excreted alone with small quantities of niacin, niacinamide, nicotinamide N-oxide, and pyridone derivatives.
The unidirectional influx of niacinamide across cerebral capillaries, the anatomical locus of the blood-brain barrier, was measured with an in situ rat brain perfusion technique employing [14C]niacinamide. Niacinamide was transported rapidly across the blood-brain barrier by a system that was not saturable with 10 mM niacinamide in the perfusate. However, with periods of perfusion longer than 30 seconds, there was substantial backflow of [14C]niacinamide into the perfusate. Niacinamide (1.7 uM) transport through the blood-brain barrier was not significantly inhibited by 3-acetylpyridine. Thus, niacinamide is transported rapidly and bidirectionally through the blood-brain barrier by a high capacity transport system. Although involved in the transfer of niacinamide between blood and brain, this transport system does not play an important regulatory role in the synthesis of NMN, NAD, and NADP from niacinamide in brain. [Spector R; Neurochem Res 12 (1): 27-31(1987)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a log Kow of -0.37(2) and a regression-derived equation(3), indicates that nicotinamide is expected to have very high mobility in soil(SRC). Volatilization of nicotinamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Nicotinamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.2X10-4 mm Hg(SRC), determined from a fragment constant method(5). Nicotinamide was determined to be readily biodegradable in an aerobic screening test(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a log Kow of -0.37(2) and a regression-derived equation(3), indicates that nicotinamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.9X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Nicotinamide was determined to be readily biodegradable in an aerobic screening test(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nicotinamide, which has an estimated vapor pressure of 4.20X10-4 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase nicotinamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7 days(SRC), calculated from its rate constant of 2.3X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase nicotinamide may be removed from the air by wet or dry deposition(SRC). Nicotinamide does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight.

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