烟酰胺

Nicotinamide

HCID 936CAS 11032-50-1

基本信息

标准SMILES
NC(=O)c1cccnc1
InChIKey
DFPAKSUCGFBDDF-UHFFFAOYSA-N
分子式
C6H6N2O
平均分子量
122.12 g/mol
单同位素质量
122.04801281

概述

Nicotinamide is a white powder. (NTP, 1992)

名称与标识

首选名称
Nicotinamide
IUPAC
pyridine-3-carboxamide
中文名
烟酰胺
英文名
Nicotinamide
分子式
C6H6N2O
分子量
122.12

名称与别名

nicotinamideniacinamide98-92-03-Pyridinecarboxamidepyridine-3-carboxamideNicotinic acid amideAminicotinAmixicotynBenicotDipegylNicofortPapulex
展开更多名称
菸酰胺菸酸胺烟酰胺烟碱酰胺尼克酰胺菸鹼醯胺精烟酰胺维生素B3维生素PP尼古丁酰胺VITAMIN B3NicotinamidnicotineamideNiaciamideNicotamideNicotinamide Bp
Nicotinic amideDelonin amidePelonin amideInovitan PPNicotilamideNicotylamideEndobionHansamid

数据库标识

CAS
11032-50-1、98-92-0
PubChem CID
936
DTXSID
DTXSID2020929
ChEMBL
CHEMBL1140
ChEBI
CHEBI:17154
UNII
25X51I8RD4
EC Number
202-713-4、234-265-0
Nikkaji
J3.988H

性质

结构计算性质

XLogP
-0.4
极性表面积
56 Ų
氢键供体
1
氢键受体
2
可旋转键
1
重原子
9

实验与物化性质

Chemical ClassesBiological Agents -> Vitamins and Derivatives
Drugs · 3 条

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Metabolite of Nikethamide

Cosmetics · 3 条

Cosmetic ingredients (Niacinamide) -> CIR (Cosmetic Ingredient Review)

Smoothing

Personal care product -> emollient -> amide

pH10% "wt in vol" solution in water is neutral to litmus
SpringerMaterials PropertiesSchoenflies notation
LogP · 4 条

log Kow = -0.37

-0.37

-0.38

-0.34

物理化学性质

熔点
128 · 128-131 °C(lit.)
沸点
150 · 150-160 °C
堆积密度
360 kg/m3 · 360kg/m3
密度
1.4 · 1.40
蒸气密度
4.22 · 4.22 (vs air)
蒸气压
0 Pa · 0Pa at 25℃

化学性质

烟酰胺是一种白色针状结晶或结晶性粉末,无臭或稍有臭气,味微苦。相对密度1.4,熔点129-131℃。1g本品可溶于1mL水、1.5mL乙醇或10mL甘油,不溶于乙醚。10%的水溶液的PH为6.5-7.5。具有微弱的吸湿性。较稳定,可耐酸、碱及 高温在干燥空气中对光、热均稳定,在碱性或酸性溶液中加热则生成烟酸。大白鼠经口LD502.5-3.5g/kg,ADI值不作特殊规定(ECC,1990)。

安全与法规

GHS分类

GHS Classification · 6 条

This chemical does not meet GHS hazard criteria for 0.3% (3 of 1154) of reports.

Warning

H315 (28.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1154 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

危害信息

Regulatory Information · 4 条

Chemical: 3-Pyridinecarboxamide

3-Pyridinecarboxamide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 3-Pyridinecarboxamide are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14571

Nicotinamide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Fire PotentialThis chemical is a noncombustible solid.
Hazards SummarySee Nicotinic acid.
FDA Requirements · 4 条

Nicotinamide-ascorbic acid complex may be safely used in accordance with the following prescribed conditions: (a) The additive is the product of the controlled reaction between ascorbic acid and nicotinamide, melting in the range 141 °C to 145 °C. (b) It is used as a source of ascorbic acid and nicotinamide in multivitamin preparations. /Nicotinamide-Ascorbic Acid Complex/

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses ... . However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: niacinamide is included in orally administered menstrual drug products and weight control drug products.

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.

安全与防护

Fire FightingUse water spray, foam, powder, carbon dioxide.
First Aid Measures · 4 条

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink.

First Aid · 1 条

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from oxidants.
Fire Fighting Procedures · 3 条

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

... Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. ... 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. The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

毒理信息

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Interactions · 5 条

Addition of 0.5 mg of nicotinamide reduced the action of dicrotophos on cultured chick embryo tibiae.

Nicotinamide will prevent depletion of NAD coenzymes by alkylating agents.

Renal oncogenic activity of Streptozotocin in male rats was significantly decreased by nicotinamide.

Oral or iv administered nicotinamide prevented Streptozotocin-induced diabetes in Rhesus monkeys and dogs.

For more Interactions (Complete) data for Nicotinamide (25 total), please visit the HSDB record page.

Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Ecotoxicity Values · 4 条

LC50; Species: Poecilia reticulata (Guppy) age 1.5-2.5 weeks; Conditions: freshwater, static, 22-23 °C, pH 7.8-8.2, dissolved oxygen >5 mg/L; Concentration: >1000 mg/L for 96 hr />99% purity/

EC50; Species: Daphnia magna (Water flea) age <24 hr; Conditions: freshwater, static, 18.5-20 °C, pH 8.1-8.2; Concentration: >1000 mg/L for 24 hr; Effect: immobilization />99% purity/

EC50; Species: Scenedesmus subspicatus (algae) strain CCAP 276/20; Conditions: freshwater, static, 21.5-25.5 °C, pH 8.1-9.9; Concentration: >1000 mg/L for 72 hr; Effect: growth inhibition />99% purity/

EC50; Species: Xenopus laevis (African clawed frog) embryos; Conditions: freshwater, renewal, 23 °C; Concentration: 340 ug/L for 96 hr (95% confidence interval: 310-360 ug/L); Effect: abnormal growth

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a structure estimation method(2), 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), developed using a fragment constant estimation method(2). Nicotinamide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.2X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Nicotinamide was determined to be readily biodegradable in an aerobic screening test(3) suggesting that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a structure estimation method(2), 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(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -0.37(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Nicotinamide was determined to be readily biodegradable in an aerobic screening test(6) suggesting that biodegradation may be an important environmental fate process in water(SRC).

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 4.2X10-4 mm Hg at 25 °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 6 days(SRC), calculated from its rate constant of 2.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase nicotinamide may be removed from the air by wet and dry deposition(SRC). Nicotinamide absorbs UV light at wavelengths >300 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 3 条

Nicotinamide is prevalent in many common foodstuffs and is especially concentrated in brewer's yeast, wheat germ and liver(1).

Nicotinic Acid and Nicotinamide (Vitamin B3) Foodstuff Content(1).

Nicotinic Acid and Nicotinamide (Vitamin B3) in Coffee(1).

法规信息

FDA Requirements · 4 条

Nicotinamide-ascorbic acid complex may be safely used in accordance with the following prescribed conditions: (a) The additive is the product of the controlled reaction between ascorbic acid and nicotinamide, melting in the range 141 °C to 145 °C. (b) It is used as a source of ascorbic acid and nicotinamide in multivitamin preparations. /Nicotinamide-Ascorbic Acid Complex/

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses ... . However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: niacinamide is included in orally administered menstrual drug products and weight control drug products.

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.

FIFRA Requirements · 1 条

Residues of nicotinamide are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Synergist. Limit: Maximum of 0.5% of formulation.

安全数据

F
8
wgk
1
tsca
TSCA listed
毒性
LD50 s.c. in rats: 1.68 g/kg (Brazda, Coulson)
RTECS号
QS3675000
存储类别
11 - Combustible Solids

毒性防护

毒性LD50 2.5~3.5g/kg(大鼠,经口)。GRAS(FDA,§182.5535,2000)。ADI不作特殊规定(EEC,1990)。

化学与工业

药理信息

ATC Code · 4 条

A11HA01

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

A11HA01

Bionecessity · 3 条

At high doses (up to 3.5 g/day), nicotinamide is protective against cell death and inhibits the production of inflammatory mediators in animal and in in vitro models of oxidant-induced cell injury.

Nicotinamide, via its major metabolite NAD+ (nicotinamide adenine dinucleotide), is involved in a wide range of biological processes, including the product of energy, the synthesis of fatty acids, cholesterol and steroids, signal transduction and the maintenance of the integrity of the genome.

In humans, niacinamide is required for lipid metabolism, tissue respiration, and glycogenolysis. In vivo, niacinamide is formed from conversion of niacin. In addition, some dietary tryptophan is oxidized to niacin and then to niacinamide in vivo. Niacinamide is incorporated into 2 coenzymes: nicotinamide adenine dinucleotide (NAD) and nicotinamide adenine dinucleotide phosphate (NADP). NAD and NADP act as hydrogen-carrier molecules in glycogenolysis, tissue respiration, and lipid metabolism.

Biological Half-LifeThe mean half life values were 2.7 hr, 5.9 hr, and 8.1 hr after taking 1, 3, or 6 g of Niacinamide, respectively.
Metabolism/Metabolites · 6 条

In amounts needed for physiologic function as a coenzyme (12-18 mg daily), niacin is converted to niacinamide; larger doses of niacin are converted to niacinamide to only a minor degree. Niacinamide is metabolized in the liver to N-methylniacinamide, other N-methylated derivatives, and nicotinuric acid (the glycine conjugate of niacin). These metabolites are excreted in urine. Following administration of physiologic doses of niacin or niacinamide, only a small amount of niacinamide is excreted unchanged in urine; however, following administration of larger doses, a greater proportion of niacin and niacinamide is excreted unchanged.

N1-Methyl-4-pyridone-3-carboxamide was detected on chromatograms of plasma extracts after oral administration of niacinamide to two human subjects.

6-Hydroxynicotinamide and 6-hydroxynicotinic acid /were detected/ as urinary metabolites by comparison of ultraviolet, infrared, and mass spectra following intraperitoneal injections of 14(C)Niacin or 14(C)Niacinamide into rats.

N1-methyl-4- pyridone-3-carboxamide is a major metabolite of niacin and niacinamide which has been found to be synthesized from N1- methylnicotinamide.

For more Metabolism/Metabolites (Complete) data for Nicotinamide (7 total), please visit the HSDB record page.

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.
Absorption, Distribution and Excretion · 5 条

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 is efficiently absorbed from the gastrointestinal tract. At low doses, absorption is mediated via sodium-dependent facilitated diffusion. Passive diffusion is the principal mechanism of absorption at higher doses. Doses of up to three to four grams of nicotinamide are almost completely absorbed. Nicotinamide is transported via the portal circulation to the liver and via the systemic circulation to the various tissues of the body. Nicotinamide enters most cells by passive diffusion and enters erythrocytes by facilitated transport.

Niacinamide is widely distributed /throughout/ 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.

For more Absorption, Distribution and Excretion (Complete) data for Nicotinamide (16 total), please visit the HSDB record page.

用途与制造

Uses · 6 条

CIR ingredient: Niacinamide

Nicotinamide is usually used to treat deficiency, because nicotinamide, unlike nicotinic acid (the most common form of niacin), does not cause flushing, itching, burning, or tingling sensations. [Merck Manual, p. 41]

Vitamin B Complex

Nicotinamide is ... used in cosmetics as hair and skin conditioning agent.

.../Has/ been used in the enrichment of bread, flour, and other grain-derived products. Animal feed is routinely supplemented with ... nicotinamide. Nicotinamide is also used in multivitamin preparations.

MEDICATION

U.S. Imports · 3 条

(1972) 1.45X10+9 GRAMS

(1975) 7.5X10+7 GRAMS (NICOTINAMIDE ONLY)

In 1980, 297.1 tons of nicotinamide were imported.

U.S. Production · 4 条

2023: 1,000,000 - <8,500,000 lb

(1972) 2.49X10+9 GRAMS (NIACIN & NICOTINAMIDE)

(1975) 2.5X10+9 GRAMS (NIACIN & NICOTINAMIDE)

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Nicotinamide:

Consumption PatternsAPPROX 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)
Consumer UsesFlavoring and nutrient
Industry UsesBrightener
应用领域 · 6 条

简介烟酰胺又称尼克酰胺、维生素B3或维生素PP,是一种水溶性维生素,属于B族维生素,为辅酶Ⅰ(烟酰胺腺嘌呤二核苷酸,NAD)和辅酶Ⅱ(烟酰胺腺嘌呤二核苷酸磷酸,NADP)的组成成分,在人体内这两种辅酶结构中的烟酰胺部分具有可逆的加氢与脱氢特性,在生物氧化中起着递氢作用,能促进组织呼吸、生物氧化过程和新陈代谢,对维持正常组织特别是皮肤、消化道和神经系统的完整性具有重要意义。缺乏时,由于细胞的呼吸和代谢受影响而引起糙皮病,故本品主要用于防治糙皮病、口炎、舌炎等。

应用烟酰胺和烟酸在大多数声合下通用,烟酸在动物体内也生成烟酰胺。体内缺乏烟酸和烟酰胺时,会得糙皮病。因此它们可预防糙皮病。它们在蛋白质和糖的新陈代谢中起作用,可改善人类和动物的营养。除用作医药外,还大量用作食品和饲料添加剂。全世界的生产能力已超过3万吨。在日本,烟酰胺用于医药占40%,饲料添加剂占50%。食品添加剂占10%。烟酸和烟酰胺无毒,在自然介多含于动物肝脏、肾脏、酵母和米糖中,烟酰胺对大鼠皮下注射LD50为1.7克/公斤。

用途一种维生素B3 以及PARP抑制剂的酰胺衍生物

用途维生素类药,参与体内代谢过程,用于防治糙皮病等烟酸缺乏症

用途烟酰胺的水溶性较烟酸好,但易与维生素C生成复合物而结块。用量30-80mg/kg。其用于护肤品可防止皮肤粗糙,维护皮肤细胞健康,促进皮肤美白。用于护发中可促进头皮血液循环,健康毛囊,促进头发生长,防止秃发。

用途生化研究;组织培养基的营养成分;临床药物为维生素B族,用于防治糙皮病及口炎、舌炎等病症的治疗。

制备方法 · 4 条

生产方法β-甲基吡啶经空气氧化成烟酸,后者与氢氧化铵作用,再加热脱水制得。

生产方法将烟酸、硼酸和氨水投入反应锅,搅拌下通入氨气,升温溶解,然后蒸馏回收氨,至120℃后移入脱水锅内继续浓缩,当温度达到145℃后开始加入液氨,并在185-190℃下继续通氨反应20-30h。然后降温至130℃,加蒸馏水稀释,加入活性炭,并在70-80℃通氨脱色2h,反应后趁热过滤,滤液在水中冷析24h,分离结晶,并用乙醇洗涤、干燥得成品,收率89%

生产方法由烟酸与氨水成盐后再脱水而得。

生产方法将烟酸、硼酸和氨水投入反应锅,搅拌下通入氨气,升温溶解;然后蒸馏回收氨,至120~C后移入脱水锅内继续浓缩;当温度达145℃后开始加入液氨,并在185~190℃下继续通氨反应20~30h。然后降温至130℃,加蒸馏水稀释,加入活性炭,并在70~80~C下通氨脱色2h;反应后趁热过滤,滤液在水中冷析24h,分离结晶,并用乙醇洗涤、干燥得成品,收率89%。

试剂价格

A15970 · 250g
烟酰胺, 99% Nicotinamide, 99% — 376元
12827 · 2.5kg
烟酰胺Nicotinamide, 99% — 2737元

供应商50 家

珠海冀百康生物科技有限公司0756-6348118 13825639916 · [email protected]
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

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