Nicotinamide
Vue d'ensemble
Description
La nicotinamide, également connue sous le nom de niacinamide, est une forme de vitamine B3. C'est une vitamine hydrosoluble essentielle pour le corps humain. La this compound se trouve dans divers aliments, notamment la levure, la viande, le lait et les légumes verts. Elle est utilisée comme complément alimentaire et médicament pour prévenir et traiter la pellagre, une maladie causée par une carence en niacine .
Applications De Recherche Scientifique
Mécanisme D'action
Target of Action
Nicotinamide, also known as Vitamin B3, primarily targets the NAD+ synthesis pathway . It is a precursor to the co-factors NAD and NADP, which play a key role in biochemical reactions, including cellular energy production and glucose metabolism . It also targets the This compound phosphoribosyltransferase (NAMPT) , the rate-limiting enzyme in the NAD salvage pathway .
Mode of Action
This compound interacts with its targets to influence human DNA repair and cellular stress responses . It is involved in the cellular energy metabolism, DNA repair, and regulation of the transcription process . It also influences the activity of several enzymes critical to basic cellular activity, such as sirtuins and poly-(ADP-ribose) polymerases (PARP) .
Biochemical Pathways
This compound affects multiple biochemical pathways. It plays a pivotal role in NAD+ synthesis , contributing to redox reactions and energy production in cells . It is also involved in the NAD salvage pathway from this compound (NAM), where NAMPT catalyzes the condensation of NAM and phosphoribosyl pyrophosphate (PRPP) into this compound mononucleotide (NMN), followed by the production of NAD via this compound mononucleotide adenylyl-transferase (NMNAT) .
Pharmacokinetics
This compound is ingested in food as part of pyridine this compound adenine dinucleotide (NAD) and this compound adenine dinucleotide phosphate (NADP) in plant and animal tissues. After the co-enzymes have separated, this compound is absorbed almost completely in the small intestine . After absorption, this compound is stored as NAD in the liver and excretion occurs via kidneys .
Result of Action
The molecular and cellular effects of this compound’s action are significant. It has been shown to significantly reduce cutaneous oxidative stress, inflammation, and pigmentation . It also plays a role in protecting neurons from traumatic injury, ischemia, and stroke . In addition, it has been implicated in key neurodegenerative conditions: Alzheimer’s, Parkinson’s, and Huntington’s diseases .
Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound. For instance, the bioavailability of this compound can be influenced by dietary intake, as it is found in small amounts in natural foods such as cow’s milk, vegetables, and meats . Furthermore, the decline in cellular or tissue NAD levels has been associated with aging and the pathophysiology of a variety of human diseases or conditions such as neurodegeneration, metabolic syndrome, and cancer .
Analyse Biochimique
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 .
Méthodes De Préparation
Voies de synthèse et conditions réactionnelles : La nicotinamide peut être synthétisée par hydrolyse de la 3-cyanopyridine. Ce processus implique la dissolution de la 3-cyanopyridine dans de l'alcool, l'ajout d'eau et d'un catalyseur, et la réalisation d'une réaction d'hydrolyse . Une autre méthode consiste à mélanger la 3-cyanopyridine avec de l'hydroxyde de sodium et à laisser le mélange réagir à une température de 70 à 75 degrés Celsius .
Méthodes de production industrielle : Commercialement, la this compound est produite à partir d'acide nicotinique ou de nicotinonitrile. Le procédé implique l'hydrolyse de ces composés dans des conditions contrôlées pour obtenir de la this compound .
Analyse Des Réactions Chimiques
Types de réactions : La nicotinamide subit diverses réactions chimiques, notamment l'oxydation, la réduction et la substitution.
Réactifs et conditions courants :
Oxydation : La this compound peut être oxydée pour former de l'acide nicotinique.
Réduction : Elle peut être réduite pour former de la 1,4-dihydrothis compound.
Substitution : La this compound peut subir des réactions de substitution où le groupe amide est remplacé par d'autres groupes fonctionnels.
Principaux produits :
Oxydation : Acide nicotinique.
Réduction : 1,4-dihydrothis compound.
Substitution : Divers dérivés substitués de la this compound.
4. Applications de la recherche scientifique
La this compound a un large éventail d'applications dans la recherche scientifique :
Médecine : Elle est utilisée dans le traitement de la pellagre, de l'acné et d'autres affections cutanées.
5. Mécanisme d'action
La this compound exerce ses effets par plusieurs mécanismes :
Métabolisme énergétique cellulaire : C'est un précurseur du NAD et du NADP, qui sont impliqués dans la production d'énergie cellulaire et les réactions redox.
Réparation de l'ADN : La this compound influence l'activité d'enzymes telles que les sirtuines et les poly-ADP ribose polymérases (PARP), qui sont essentielles pour la réparation de l'ADN et les réponses au stress cellulaire.
Effets anti-inflammatoires : Elle inhibe l'activation de facteurs de transcription comme NF-κB et AP-1, réduisant l'inflammation.
Comparaison Avec Des Composés Similaires
La nicotinamide est souvent comparée à d'autres formes de vitamine B3, telles que l'acide nicotinique et le this compound riboside :
Acide nicotinique : Contrairement à la this compound, l'acide nicotinique peut provoquer des bouffées de chaleur cutanées.
This compound riboside : Ce composé est un précurseur du this compound mononucléotide (NMN) et du NAD.
Composés similaires :
- Acide nicotinique
- This compound riboside
- This compound mononucléotide (NMN)
La this compound se distingue par son large éventail d'applications et ses effets secondaires minimes, ce qui en fait un composé précieux dans divers domaines.
Propriétés
IUPAC Name |
pyridine-3-carboxamide |
Source
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|---|---|---|
| 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
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| 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
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| Record name | Niacinamide | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID2020929 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
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
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| 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 | 3-Pyridinecarboxamide | |
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| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0001406 | |
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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
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| Record name | NICOTINAMIDE | |
| Source | CAMEO Chemicals | |
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| Record name | Nicotinamide | |
| Source | DrugBank | |
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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
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| Record name | NICOTINAMIDE | |
| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
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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
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| 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 | |
| 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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| 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. | |
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| Source | ILO-WHO International Chemical Safety Cards (ICSCs) | |
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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 | |
| 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 | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/1237 | |
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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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| URL | https://www.ilo.org/dyn/icsc/showcard.display?p_version=2&p_card_id=1703 | |
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Vapor Pressure |
Vapor pressure, kPa at 35 °C: 3.1 |
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 | |
| 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. | |
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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 | |
| 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 | 3-Pyridinecarboxamide | |
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| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.002.467 | |
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| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | NIACINAMIDE | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/25X51I8RD4 | |
| Description | The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions. | |
| Explanation | Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required. | |
| 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 | |
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
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Retrosynthesis Analysis
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Feasible Synthetic Routes
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Veuillez noter que tous les articles et informations sur les produits présentés sur BenchChem sont destinés uniquement à des fins informatives. Les produits disponibles à l'achat sur BenchChem sont spécifiquement conçus pour des études in vitro, qui sont réalisées en dehors des organismes vivants. Les études in vitro, dérivées du terme latin "in verre", impliquent des expériences réalisées dans des environnements de laboratoire contrôlés à l'aide de cellules ou de tissus. Il est important de noter que ces produits ne sont pas classés comme médicaments et n'ont pas reçu l'approbation de la FDA pour la prévention, le traitement ou la guérison de toute condition médicale, affection ou maladie. Nous devons souligner que toute forme d'introduction corporelle de ces produits chez les humains ou les animaux est strictement interdite par la loi. Il est essentiel de respecter ces directives pour assurer la conformité aux normes légales et éthiques en matière de recherche et d'expérimentation.
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