Nicotinamide
Número de catálogo:
B372718
Número CAS:
98-92-0
Peso molecular:
122.12 g/mol
Clave InChI:
DFPAKSUCGFBDDF-UHFFFAOYSA-N
Atención:
Solo para uso de investigación. No para uso humano o veterinario.
Descripción general
Descripción
La nicotinamida, también conocida como niacinamida, es una forma de vitamina B3. Es una vitamina soluble en agua que es esencial para el cuerpo humano. La nicotinamida se encuentra en varios alimentos, incluidos la levadura, la carne, la leche y las verduras de hoja verde. Se utiliza como suplemento dietético y medicamento para prevenir y tratar la pelagra, una condición causada por la deficiencia de niacina .
Mecanismo De Acción
La nicotinamida ejerce sus efectos a través de varios mecanismos:
Metabolismo energético celular: Es un precursor de NAD y NADP, que participan en la producción de energía celular y las reacciones redox.
Efectos antiinflamatorios: Inhibe la activación de factores de transcripción como NF-κB y AP-1, reduciendo la inflamación.
Análisis Bioquímico
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 .
Métodos De Preparación
Rutas sintéticas y condiciones de reacción: La nicotinamida se puede sintetizar mediante la hidrólisis de 3-cianopiridina. Este proceso implica disolver 3-cianopiridina en alcohol, agregar agua y un catalizador, y realizar una reacción de hidrólisis . Otro método consiste en mezclar 3-cianopiridina con hidróxido de sodio y dejar que la mezcla reaccione a una temperatura de 70 a 75 grados Celsius .
Métodos de producción industrial: Comercialmente, la nicotinamida se produce a partir de ácido nicotínico o nicotinonitrilo. El proceso implica la hidrólisis de estos compuestos en condiciones controladas para producir nicotinamida .
Análisis De Reacciones Químicas
Tipos de reacciones: La nicotinamida experimenta diversas reacciones químicas, incluidas la oxidación, la reducción y la sustitución.
Reactivos y condiciones comunes:
Oxidación: La nicotinamida se puede oxidar para formar ácido nicotínico.
Reducción: Se puede reducir para formar 1,4-dihidronicotinamida.
Sustitución: La nicotinamida puede sufrir reacciones de sustitución en las que el grupo amida es reemplazado por otros grupos funcionales.
Productos principales:
Oxidación: Ácido nicotínico.
Reducción: 1,4-dihidronicotinamida.
Sustitución: Diversos derivados de nicotinamida sustituidos.
Aplicaciones Científicas De Investigación
Comparación Con Compuestos Similares
La nicotinamida se compara a menudo con otras formas de vitamina B3, como el ácido nicotínico y la nicotinamida ribósido:
Ácido nicotínico: A diferencia de la nicotinamida, el ácido nicotínico puede causar enrojecimiento de la piel.
Nicotinamida ribósido: Este compuesto es un precursor del mononucleótido de nicotinamida (NMN) y el NAD.
Compuestos similares:
- Ácido nicotínico
- Nicotinamida ribósido
- Mononucleótido de nicotinamida (NMN)
La nicotinamida destaca por su amplia gama de aplicaciones y efectos secundarios mínimos, lo que la convierte en un compuesto valioso en varios campos.
Propiedades
IUPAC Name |
pyridine-3-carboxamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| 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
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
DFPAKSUCGFBDDF-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| 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 | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20736 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | NICOTINAMIDE | |
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| Record name | nicotinamide | |
| Source | Wikipedia | |
| URL | https://en.wikipedia.org/wiki/Nicotinamide | |
| Description | Chemical information link to Wikipedia. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID2020929 |
Source
|
| Record name | Niacinamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID2020929 | |
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Molecular Weight |
122.12 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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
|
| 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 | |
| Source | CAMEO Chemicals | |
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| Record name | Nicotinamide | |
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| Record name | Nicotinamide | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1237 | |
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Flash Point |
182 °C |
Source
|
| Record name | NICOTINAMIDE | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=1703 | |
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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 | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | NICOTINAMIDE | |
| Source | CAMEO Chemicals | |
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| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Nicotinamide | |
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| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001406 | |
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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
|
| Record name | NICOTINAMIDE | |
| Source | CAMEO Chemicals | |
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| Record name | NICOTINAMIDE | |
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Vapor Density |
Relative vapor density (air = 1): 4.2 |
Source
|
| Record name | NICOTINAMIDE | |
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Vapor Pressure |
Vapor pressure, kPa at 35 °C: 3.1 |
Source
|
| Record name | NICOTINAMIDE | |
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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
|
| Record name | NICOTINAMIDE | |
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| URL | https://cameochemicals.noaa.gov/chemical/20736 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| URL | http://www.hmdb.ca/metabolites/HMDB0001406 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
| Record name | NICOTINAMIDE | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=1703 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
Melting Point |
264 to 268 °F (NTP, 1992), 128.8 °C, 130 °C, 127-131 °C |
Source
|
| Record name | NICOTINAMIDE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20736 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
| Explanation | CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data. | |
| Record name | Nicotinamide | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB02701 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Nicotinamide | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1237 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Niacinamide | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001406 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
| Record name | NICOTINAMIDE | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=1703 | |
| Description | The International Chemical Safety Cards (ICSCs) are data sheets intended to provide essential safety and health information on chemicals in a clear and concise way. The primary aim of the Cards is to promote the safe use of chemicals in the workplace. | |
| Explanation | Creative Commons CC BY 4.0 | |
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
potassium phosphate
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two
[Compound]
Name
mixture
Quantity
30 mL
Type
solvent
Reaction Step Three
Name
Yield
97.3%
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
Name
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
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.
Retrosynthesis Analysis
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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
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Reactant of Route 3
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Reactant of Route 5
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Reactant of Route 6
Nicotinamide
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