Nicotinamide

Cat. No.: B372718

CAS No.: 98-92-0

M. Wt: 122.12 g/mol

InChI Key: DFPAKSUCGFBDDF-UHFFFAOYSA-N

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Overview

1. Description

8. Properties

2. Mechanism of action

9. Synthesis routes and methods I

3. Biochemical analysis

10. Synthesis routes and methods II

4. Preparation methods

11. Synthesis routes and methods III

5. Chemical reactions analysis

12. Synthesis routes and methods IV

6. Scientific research applications

13. Retrosynthesis analysis

7. Comparison with similar compounds

14. Disclaimer

Description

Nicotinamide, also known as niacinamide, is a form of vitamin B3. It is a water-soluble vitamin that is essential for the human body. This compound is found in various foods, including yeast, meat, milk, and green vegetables. It is used as a dietary supplement and medication to prevent and treat pellagra, a condition caused by niacin deficiency .

Mechanism of Action

Biochemical Analysis

Biochemical Properties

Nicotinamide plays a critical role in a myriad of important biological processes including metabolism, DNA damage response, inflammation, cancer, neurodegeneration, and aging . It interacts with enzymes such as this compound phosphoribosyltransferase (NAMPT), which converts this compound and 5-phosphoribosyl pyrophosphate into this compound mononucleotide (NMN), a precursor to NAD+.

Cellular Effects

This compound influences cell function by regulating numerous pathways, such as cell apoptosis, cell proliferation, and energy metabolism . It impacts cell signaling pathways, gene expression, and cellular metabolism .

Molecular Mechanism

This compound exerts its effects at the molecular level through binding interactions with biomolecules, enzyme inhibition or activation, and changes in gene expression . For instance, it is involved in the synthesis of NMN, which is then converted to NAD+.

Temporal Effects in Laboratory Settings

In laboratory settings, the effects of this compound can change over time. This includes information on the product’s stability, degradation, and any long-term effects on cellular function observed in in vitro or in vivo studies .

Dosage Effects in Animal Models

The effects of this compound vary with different dosages in animal models. This includes any threshold effects observed in these studies, as well as any toxic or adverse effects at high doses .

Metabolic Pathways

This compound is involved in several metabolic pathways. It interacts with enzymes or cofactors, and can also affect metabolic flux or metabolite levels .

Transport and Distribution

This compound is transported and distributed within cells and tissues. This includes any transporters or binding proteins that it interacts with, as well as any effects on its localization or accumulation .

Subcellular Localization

The subcellular localization of this compound and any effects on its activity or function could include any targeting signals or post-translational modifications that direct it to specific compartments or organelles .

Preparation Methods

Synthetic Routes and Reaction Conditions: Nicotinamide can be synthesized through the hydrolysis of 3-cyanopyridine. This process involves dissolving 3-cyanopyridine in alcohol, adding water and a catalyst, and performing a hydrolysis reaction . Another method involves mixing 3-cyanopyridine with sodium hydroxide and allowing the mixture to react at a temperature of 70 to 75 degrees Celsius .

Industrial Production Methods: Commercially, this compound is produced from either nicotinic acid or nicotinonitrile. The process involves the hydrolysis of these compounds under controlled conditions to yield this compound .

Chemical Reactions Analysis

Types of Reactions: Nicotinamide undergoes various chemical reactions, including oxidation, reduction, and substitution.

Common Reagents and Conditions:

Oxidation: this compound can be oxidized to form nicotinic acid.

Reduction: It can be reduced to form 1,4-dihydrothis compound.

Substitution: this compound can undergo substitution reactions where the amide group is replaced by other functional groups.

Major Products:

Oxidation: Nicotinic acid.

Reduction: 1,4-dihydrothis compound.

Substitution: Various substituted this compound derivatives.

Scientific Research Applications

Nicotinamide has a wide range of applications in scientific research:

Chemistry: It is used as a precursor in the synthesis of this compound adenine dinucleotide (NAD) and this compound adenine dinucleotide phosphate (NADP), which are essential coenzymes in redox reactions.

Biology: this compound plays a crucial role in cellular energy metabolism, DNA repair, and regulation of transcription processes.

Medicine: It is used in the treatment of pellagra, acne, and other skin conditions.

Industry: this compound is used in the formulation of skincare products and cosmetics due to its anti-inflammatory and anti-aging properties.

Comparison with Similar Compounds

Nicotinic acid
Nicotinamide riboside
This compound mononucleotide (NMN)

This compound stands out due to its broad range of applications and minimal side effects, making it a valuable compound in various fields.

Properties

IUPAC Name	pyridine-3-carboxamide	Source
Source	PubChem
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Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)	Source
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Description	Data deposited in or computed by PubChem

InChI Key	DFPAKSUCGFBDDF-UHFFFAOYSA-N	Source
Source	PubChem
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Description	Data deposited in or computed by PubChem

Canonical SMILES	C1=CC(=CN=C1)C(=O)N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C6H6N2O	Source
Record name	NICOTINAMIDE
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Record name	NICOTINAMIDE
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Record name	nicotinamide
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URL	https://en.wikipedia.org/wiki/Nicotinamide
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DSSTOX Substance ID	DTXSID2020929	Source
Record name	Niacinamide
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Molecular Weight	122.12 g/mol	Source
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Physical Description	Nicotinamide is a white powder. (NTP, 1992), Dry Powder; Other Solid, Colorless needles or white crystalline powder. Bitter taste., Solid, WHITE CRYSTALLINE POWDER.	Source
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Record name	NICOTINAMIDE
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Boiling Point	302 to 320 °F at 760 mmHg (NTP, 1992), BP: 157 °C at 5X10-4 atm, BP: 150-160 at 0.67 Pa. Sublimation range 80-100 °C	Source
Record name	NICOTINAMIDE
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Record name	Nicotinamide
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Flash Point	182 °C	Source
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Solubility	2.8 [ug/mL] (The mean of the results at pH 7.4), greater than or equal to 100 mg/mL at 70 °F (NTP, 1992), In water, 5X10+5 mg/L at 25 °C, Very soluble in water; 1 g is soluble in 1 mL water, 1 g dissolves in about 1 mL water, in 10 mL glycerol, in about 1.5 mL alcohol, Soluble in butanol, chloroform, For more Solubility (Complete) data for Nicotinamide (6 total), please visit the HSDB record page., 500 mg/mL at 25 °C, Solubility in water, g/100ml at 20 °C: 100 (very good)	Source
Record name	SID8139965
Source	Burnham Center for Chemical Genomics
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Description	Aqueous solubility in buffer at pH 7.4

Record name	NICOTINAMIDE
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Density	1.4 (NTP, 1992) - Denser than water; will sink, 1.400 g/cu cm at 25 °C, Specific heat = solid, 55 °C: 1.30 kJ/kg; heat of solution in water: -148 kJ/kg; heat of fusion: 381 kJ/kg; density of melt, at 150 °C: 1.19 g/cu cm, 1.4 g/cm³	Source
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Vapor Density	Relative vapor density (air = 1): 4.2	Source
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Vapor Pressure	Vapor pressure, kPa at 35 °C: 3.1	Source
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Color/Form	White, powder, needles from benzene, Colorless crystalline solid, White, crystalline powder, Colorless needles
CAS No.	98-92-0	Source
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Melting Point	264 to 268 °F (NTP, 1992), 128.8 °C, 130 °C, 127-131 °C	Source
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Synthesis routes and methods I

Procedure details

The reaction was carried out in a reaction mixture (30 ml), comprising 500 mM 3-cyanopyridine, 40 mM potassium phosphate buffer (pH 7.0) and resting cells (dry weight 2.3 mg). During the reaction, 3-cyanopyridine (500 mM) was added 7 times as soon as it was consumed. In this manner, 4.0 M 3-cyanopyridine was added in the course of 15 h and 3.89 M (475 g/l) nicotinamide was formed, corresponding to a yield of 97.3%. Nicotinic acid was not formed.

Name

3-cyanopyridine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

potassium phosphate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

[Compound]

Name

mixture

Quantity

30 mL

Type

solvent

Reaction Step Three

Name

nicotinamide

Yield

97.3%

Details

Synthesis routes and methods II

Procedure details

High performance liquid chromatography was used to detect Nampt reaction products. HPLC was performed with Waters 515 pumps and a 2487 detector (Waters, Mass.) with a Supelco LC-18-T column (15 cm×4.6 cm; Supelco, Pa.). The Nampt reaction was conducted at 37° C. for 15 min in 500 μl of reaction buffer (50 mM Tris-HCl [pH 7.5], 10 mM MgCl2, 50 mM nicotinamide, 0.2 mM PRPP) with 50 μg of the recombinant Nampt protein. The reaction was terminated by adding 125 μl of 1 M HClO4. Protein was then precipitated at 18,000 g, and 500 μl of the supernatant was neutralized with 40 μl of 3 M K2CO3. After centrifugation, 100 μl of sample was mixed with 400 μl of Buffer A (50 mM K2PO4/KHPO4, pH 7.0) and loaded into the HPLC system. The products from Nampt reaction were monitored by absorbance at 261 nm. Results of HPLC detection of Nampt reaction products showed that the mouse Nampt produced nicotinamide mononucleotide (NMN) from nicotinamide and PRPP (see, e.g., FIG. 4D). Nampt failed to catalyze the synthesis of nicotinic acid mononucleotide (NaMN) from nicotinic acid and PRPP (see, e.g., FIGS. 13A and 13B), confirming the substrate specificity of this enzyme. In isolated reactions, it was also confirmed that Nmnat catalyzed the synthesis of NAD from NMN and ATP.

Name

Tris-HCl

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

MgCl2

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

nicotinamide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

PRPP

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

nicotinamide mononucleotide

Name

nicotinamide

Name

PRPP

Details

Synthesis routes and methods III

Procedure details

0.096 mole of 3-cyanopyridine was dissolved in 5.556 mole of water and 0.0115 mole of MnO2, prepared by above method, was added to this. The mixture was refluxed at 105° C. for 8 hrs. The reaction mixture was cooled and filtered. The filtrate was evaporated in dryness to get solid nicotinamide 0.095 mole. Yield of isonicotinamide was 98.9 mole %.

Name

3-cyanopyridine

Quantity

0.096 mol

Type

reactant

Reaction Step One

Name

water

Quantity

5.556 mol

Type

reactant

Reaction Step One

Name

MnO2

Quantity

0.0115 mol

Type

catalyst

Reaction Step Two

Name

nicotinamide

Details

Synthesis routes and methods IV

Procedure details

In this Example a USP grade nicotinamide product was recovered from a crude nicotinamide product medium. The crude contained 39.7% nicotinamide, 2.15% sodium nicotinate and 0.14% 3-cyanopyridine. These and all other percentages given in this Example are percentages by weight unless indicated otherwise. The total sodium content of the medium was 0.38%. On a dry basis, the reaction crude contained 93.7% nicotinamide, 5.07% sodium nicotinate, 0.33% 3-cyanopyridine, and 0.9% total sodium. Cation and weak base resins were utilized in the recovery process. The cation exchange resin was Dowex Marathon C, a sulfonated copolymer of styrene and divinylbenzene (gel form). The weak base resin was Dowex Marathon WBA, a dimethylamine-functionalized chloromethylated copolymer of styrene and divinylbenzene (macroporous form with a monodisperse size distribution). After washing with deionized water, these resins were loaded into columns each having an inner diameter of 15 mm and a height of 30 cm, leaving about 1.5 inches head space at the top of the columns. The reaction crude was then successively treated over the cation-exchange resin (at 28 ml/min), the weak base resin (20 ml/min), the cation-exchange resin (28 ml/min), and the weak base resin (20 ml/min). The cation-exchange resin was regenerated after every ten bed volumes of reaction crude, by a cycle that included a water wash (20 ml/min, 1.25 bed volumes), a 12% sulfuric acid strip (7 ml/min, 1 bed volume), and another water wash (20 ml/min, 1.25 bed volumes). The weak base resin was regenerated after every five bed volumes of reaction crude, by a cycle including a water wash (20 ml/min, 1.6 bed volumes), a 4% sodium hydroxide strip (20 ml/min, 1 bed volume), and another water wash (2.6 bed volumes). The feeds were analyzed by HPLC after the first pass cation-exchange and weak base, and second pass cation-exchange and weak base. Typical results from such experiments are presented in Table 1 below, top. The lower section of Table 1 gives a typical product analysis on a water free basis. The extreme right hand column of Table 1 sets out the results of an analysis of the product after recovery by evaporation (no crystallization performed). As can be seen, this processing reduced the 0.9% initial sodium to an undetectable level, and the initial 5.07% nicotinate to 0.13% (as nicotinic acid) on a dry weight basis, providing a USP grade nicotinamide.

Name

sodium nicotinate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

3-cyanopyridine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

sodium

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Three

Name

styrene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

divinylbenzene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Five

Name

dimethylamine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Six

Name

styrene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Seven

Name

divinylbenzene

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Eight

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Nine

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Ten

Name

water

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Eleven

Name

nicotinamide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Twelve

Name

nicotinamide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Thirteen

Name

nicotinamide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Fourteen

Name

sodium nicotinate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Fifteen

Name

3-cyanopyridine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step 16

Name

sodium

Quantity

0 (± 1) mol

Type

reactant

Reaction Step 17

Name

nicotinamide

Quantity

0 (± 1) mol

Type

reactant

Reaction Step 18

Name

nicotinate

Yield

5.07%

Name

nicotinic acid

Name

nicotinamide

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.

Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Nicotinamide

Reactant of Route 2

Nicotinamide

Reactant of Route 3

Nicotinamide

Reactant of Route 4

Nicotinamide

Reactant of Route 5

Nicotinamide

Reactant of Route 6

Nicotinamide

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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.

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