1341-23-7 Usage
Description
Nicotinamide Riboside (NR) is a next-generation vitamin B3 that occurs naturally in trace amounts in milk. It is a pyridine nucleoside consisting of nicotinamide with a beta-D-ribofuranosyl moiety at the 1-position and is a metabolite found in or produced by Saccharomyces cerevisiae. NR is an orally available form of vitamin B3 and a precursor of nicotinamide adenine dinucleotide (NAD+). It has a unique metabolism compared to other forms of vitamin B3, such as nicotinamide and nicotinic acid, and has been shown to be the most effective form at increasing NAD+ levels. NR does not bind to the receptor responsible for flushing, making it a promising candidate for various applications.
Uses
Used in Biomedical Research:
Nicotinamide Riboside is used as a research tool for studying gene circadian reprogramming transcriptome in the liver, which helps identify metabolic pathways of aging in mice.
Used in Pharmaceutical Industry:
NR is used as a potential treatment for chemotherapy-induced peripheral neuropathy (CIPN) due to its role as a precursor of NAD+.
Used in Neurological Applications:
Nicotinamide Riboside is used as a neuroprotective agent for increasing NAD+ levels in the cerebral cortex, which helps reduce cognitive deterioration in transgenic mouse models of Alzheimer's disease.
Used in Nutritional Supplements:
NR can be used as an ingredient in nutritional supplements to boost NAD+ levels, which may have potential health benefits due to its role in various cellular processes.
Used in Aging Research:
Nicotinamide Riboside is used as a compound for studying the effects of NAD+ synthesis on aging and age-related diseases, as it can be used by cells to make NAD+ without the enzymatic step that requires NAMPT.
benefits
Nicotinamide riboside (NR) is one of the viable natural precursors for the biosynthesis of NAD+ via two alternative pathways involving the purine nucleoside phosphorylase or the nicotinamide riboside kinase enzymes. Therapeutic benefits of nicotinamide riboside supplementation:Constant dietary supplementation of nicotinamide riboside has been shown to increase the NAD+ levels in middle aged to elderly people.It may support mitochondrial function.It may enhance memory and combat cognitive decline.It might lengthen your life.It might promote muscle quality and strength.It might counter the effects of a high-fat diet.In 2016 NR received the GRAS (Generally Recognized As Safe) status from the FDA. NR also demonstrated the potential to slow aging processes in mice models.
Biological Functions
Nicotinamide adenine dinucleotide (NAD+) is a critical coenzyme that, when reduced to NADH, serves as a reducing agent to donate electrons for oxidative phosphorylation and ATP synthesis in mitochondria. NAD+ is a critical cofactor for enzymes such as sirtuins, ADP-ribosyltransferases (ARTs), and Poly [ADP- ribose] polymerases (PARPs) and is continuously consumed by these enzymes. The NAD+/NADH ratio is a critical component of the redox state of the cell. (Verdin 2015). By some counts, NAD or the related NADP participates in a quarter of all cellular reactions (Opitz Heiland 2015). There are separate compartments of NAD+ in the nucleus, mitochondria, and cytoplasm (Verdin 2015). Nicotinamide riboside (NR) can be converted into NAD+ through an intermediate step in which it is converted into nicotinamide mononucleotide (NMN) by NR kinase (Nrk) and then to NAD+ by NMNATs. NR is naturally found in some foods but at very low quantities (e.g. low micromolar range). Historically, NR was difficult to obtain in large purified amounts, but thanks to advances in synthesis methods (Yang 2007), as of June 2013, it is sold as a dietary supplement.
Clinical Use
Nicotinamide riboside is important because it is a potent and bioavailable pre-cursor to NAD+. NAD+ is essential to life and is known to be vital to functions that ensure proper cellular and energy metabolism. The most well-known function of NAD+ is the transferring of electrons to the machinery in the cell that produces ATP, the energy currency of all cells. NAD+ is increasingly being shown to have important functions beyond electron transfer. One of the most promising potential roles for NR as a pre-cursor to NAD+ is activation of sirtuins, enzymes associated with a wide variety of functions related to metabolism and longevity.
Side effects
No serious adverse effects have been reported in human studies, though most of the studies so far have been short in duration and low in participant numbers. The need for larger scale and more robust human studies is critical if NR is to be properly evaluated.To date, some people have reported mild to moderate side effects, including nausea, fatigue, headaches, diarrhea, stomach upset and indigestion. While that seems to suggest NR is likely safe, the lack of large scale long-term studies means that this cannot be confirmed.As always, if you do decide to take a NR supplement and experience any adverse effects, you should cease taking it immediately and consult your doctor.
Safety
Nicotinamide riboside has a successful New Dietary Ingredient Notification with FDA (NDIN 882) for daily recommended intake of not more than 180 mg/d.Nicotinamide riboside is generally recognized as safe (FDA GRAS Notice No. 635) for use in vitamin waters, protein shakes, nutrition bars, gum, chews, and powdered beverages. Maximum use level 0.0057% by weight.
Mode of action
NAD+ is a critical and often rate-limiting factor in many aspects of mitochondrial and cellular function including DNA repair by PARPs, widespread acetylation and epigenetic effects by sirtuins, efficient production of ATP, and other pathways (Stein & Imai 2012). NAD+ levels decline with age as does the ratio of NAD+/NADH, with numerous studies suggesting that blunting this decline with NAD+ precursors or genetic manipulations can blunt fundamental features of aging (see below). The levels also decline with the high-fat diet but increase with calorie restriction and fasting (Stein & Imai 2012), leading some to argue that it can function as a calorie restriction mimetic.www.alzdiscovery.org
Check Digit Verification of cas no
The CAS Registry Mumber 1341-23-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,3,4 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1341-23:
(6*1)+(5*3)+(4*4)+(3*1)+(2*2)+(1*3)=47
47 % 10 = 7
So 1341-23-7 is a valid CAS Registry Number.
InChI:InChI=1/C11H13NO3/c13-10(6-7-12-8-11(14)15)9-4-2-1-3-5-9/h1-5,12H,6-8H2,(H,14,15)
1341-23-7Relevant articles and documents
Syntheses of nicotinamide riboside and derivatives: Effective agents for increasing nicotinamide adenine dinucleotide concentrations in mammalian cells
Yang, Tianle,Chan, Noel Yan-Ki,Sauve, Anthony A.
, p. 6458 - 6461 (2007)
A new two-step methodology achieves stereoselective synthesis of β-nicotinamide riboside and a series of related amide, ester, and acid nucleosides. Compounds were prepared through a triacetylatednicotinate ester nucleoside, via coupling of either ethylnicotinate or phenylnicotinate with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose. Nicotinamide riboside, nicotinic acid riboside, O-ethylnicotinate riboside, O-methylnicotinate riboside, and several N-alkyl derivatives increased NAD+ concentrations from 1.2-2.7-fold in several mammalian cell lines. These findings establish bioavailability and potent effects of these nucleosides in stimulating the increase of NAD+ concentrations in mammalian cells.
Chemical synthesis method of beta-nicotinamide mononucleotide
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Paragraph 0040; 0044-0045, (2021/11/10)
The invention provides a chemical synthesis method of beta-nicotinamide mononucleotide. The method comprises the following steps: taking 1, 2, 3, 5-tetrabenzoyloxy-2-C-methyl-beta-D-ribofuranose and nicotinamide as initial raw materials, and sequentially carrying out condensation reaction, benzoyl protecting group removal and phosphorylation reaction, so as to prepare the beta-nicotinamide mononucleotide. The high-purity beta-nicotinamide mononucleotide can be obtained through three steps of reaction (each step of reaction does not need purification) and one step of desalination purification. The method has the advantages of easily available raw materials, short reaction route, simple post-treatment, environmental protection and high total reaction yield, and is suitable for industrial production.
Β - nicotinamide mononucleotide preparation method
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, (2021/10/27)
The invention discloses a preparation method of β - nicotinamide mononucleotide. The preparation method of β - nicotinamide mononucleotide comprises the following steps: S1: in the presence of first solvent and catalyst, nicotinate and tetraacetyl - D - ribose undergo condensation reaction in first microchannel reactor to obtain the material A. The temperature of the condensation reaction is 51 - 80 °C, and the residence time of the condensation reaction is 0.5 - 10 min. S2: Material A Removal first of the solvent gives material B. S3: In the presence of second solvent, the material B and the liquid ammonia are subjected to an ammonolysis reaction to obtain the material C. S4: The mixture of material C and third solvent removed second solvent and unreacted liquid ammonia to give material D. S5: The material D phosphorylates and reacts with the phosphorylation auxiliary to obtain. The β - nicotinamide mononucleotide preparation method can effectively shorten the reaction time, improve the production efficiency, lower the side reaction and improve the product yield.
Process preparation method of beta-nicotinamide mononucleotide
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, (2020/08/26)
The invention provides a process preparation method of beta-nicotinamide mononucleotide. With tetraacetylribose and niacinamide or ethyl nicotinate as starting materials, through main process steps ofcondensation, ammonolysis, chemical resolution, phosphorylation and the like, and through optimization of the process method, the beta-nicotinamide mononucleotide is prepared; the method is based onthe purposes of quality control and safety of the beta-nicotinamide mononucleotide, industrial batch production feasibility of a preparation process and the like; the preparation method is improved onthe basis of an original process route, optimizes the selected materials and reagents, controls the material amount and the like, and has the advantages of simplicity in operation, easiness in process amplification, higher yield, controllable final product quality, controllable safety and the like compared with the original preparation process.