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Nicotinamide riboside chloride

Nicotinamide Riboside Chloride(NRC)

CAS: 23111-00-4

Molecular Formula: C11H15N2O5.Cl

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Nicotinamide riboside chloride - Names and Identifiers

Name Nicotinamide Riboside Chloride(NRC)
Synonyms Nicotinamide Riboside.Cl
Nicotimide riboside chloride
Nicotinamide riboside chloride
Nicotinamide Riboside Chloride(NRC)
Nicotinamide B-D Riboside Chloride(WX900111)
3-Carbamoyl-1-(β-D-ribofuranosyl)pyridinium chloride
3-Carbamoyl-1-beta-D-ribofuranosylpyridinium chloride
3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium chloride
CAS 23111-00-4
EINECS 200-184-4

Nicotinamide riboside chloride - Physico-chemical Properties

Molecular FormulaC11H15N2O5.Cl
Molar Mass290.7002
Solubility Soluble to 100 mM in DMSO and to 100 mM in water
Storage Conditionunder inert gas (nitrogen or Argon) at 2-8°C

Nicotinamide riboside chloride - Reference

Reference
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1. LI, Yan, et al. Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model. Neuroreport, 2018, 29.15: 1264-1268.

Nicotinamide riboside chloride - Reference Information

Introduction nicotinamide riboside is a precursor of nicotinamide adenine dinucleotide (NAD) and represents a source of vitamin B3. Recent studies have shown that new health benefits can be obtained by ingesting larger amounts of nicotinamide riboside than naturally occurring in food products.
nicotinamide mononucleotide plays an important role in the energy production of human cells. It is involved in the synthesis of intracellular NAD (nicotinamide adenine dinucleotide, an important coenzyme for cell energy conversion).
description nicotinamide riboside chloride is a crystalline form of nicotinamide riboside (NR) chloride, known as NIAGEN, it is generally considered safe (GRAS) and can be used in food and dietary supplements. Nicotinamide riboside is a source of vitamin B3 (niacin) that enhances oxidative metabolism and prevents metabolic abnormalities caused by a high-fat diet. Nicotinamide riboside is a newly discovered NAD (NAD) precursor vitamin.
uses nicotinamide riboside has been implicated in increasing tissue NAD concentrations and inducing insulin sensitivity as well as enhancing sirtuin function. Its ability to increase NAD production suggests that nicotinamide riboside can also improve mitochondrial health, stimulate mitochondrial function, and induce the production of new mitochondria. Other studies using nicotinamide riboside in models of Alzheimer's disease have shown that the molecule is bioavailable to the brain and may provide neuroprotection by stimulating NAD synthesis in the brain.
In addition, a study in 2012 observed a 60% reduction in body weight gain in mice fed a high fat diet supplemented with nicotinamide riboside compared to mice fed the same high fat diet without nicotinamide riboside. Nicotinamide riboside chloride (3-carbamoyl-1-[(2R,3R,4S5R)-3, 4-dihydroxy-5-(hydroxymethyl)) oxyheterocyclopentan-2-yl]-pyridin-1-ium chloride; Also known as 1-(β-D-ribofuranosyl) nicotinamide chloride) is a known salt form of nicotinamide riboside, despite the useful attributes of nicotinamide riboside and its chloride salts (e. G., in pharmaceutical or nutritional supplements), improvements are often needed.
production method The residue was transferred back to a 20L reactor with L of methanol. An ice bath was applied to the reactor to adjust the internal temperature to 3 °c. On the other hand, 3.75L(3.75mol) of 1m naoch3 in methanol was cooled to 3 °c, and then the solution was added to the reactor over 10 minutes. During the addition, the internal temperature was kept below 5 °c. After the addition was complete, the reaction mixture was stirred for 30 minutes, then 1.25L(3.75mol) of 3M HCl was added slowly, keeping the internal temperature below 5 °c. At the end of the addition of HCl, pH = 3. The solvent was removed under vacuum. (For convenience, the partially concentrated solution may be stored at 4 °c for up to 48h). After completion of the concentration, the residue can be stored at -20 °c for up to 18h. To remove residual methanol, the evaporation residue was dissolved in water and concentrated under vacuum (3x 1L). The residue was taken up in 5L of water and the pH was adjusted to 4 with 2M NaOH (aq). Sodium chloride (NaCl) was added to the solution and the mixture was stirred at room temperature until NaCl was saturated, leaving about 5g of undissolved NaCl.
with tetrahydrofuran (THF, 3x 5L) the saturated solution was extracted. The aqueous layer was monitored by 1H NMR to confirm that the acetic acid had been removed after the extraction was complete. The aqueous phase was adjusted to pH = 6-7 with 2M NaOH (AQ) and then extracted with THF(4x 5L). The aqueous layer was monitored by 1H NMR to confirm that the residual nicotinamide was <5mol% relative to the nicotinamide riboside. 19F NMR was also used to confirm the absence of triflate in the aqueous layer. The aqueous layer was then concentrated under vacuum to remove 2.5L of water. The residual suspension was diluted with 5L of ethanol, filtered, and the salt precipitate washed with 2.5L of ethanol. The combined filtrate and washings were concentrated to a viscous oil under vacuum. It was stirred with 1.5L of methanol, the precipitate was filtered, and the solution was concentrated under vacuum. The residue was additionally stirred with 1.5L of methanol, the precipitate was filtered and the solution was concentrated under vacuum. The residue was stirred with a third portion of 1.5L of methanol, the precipitate was filtered, and the solution was concentrated under vacuum to obtain 385g of an orange-red oil. The amount of residual methanol was confirmed to be 34g by 1H NMR, and the yield of the crude product was 77% g (). The THF extract was used to remove most of the excess nicotinamide.
biological activity Nicotinamide Riboside Chloride (NIAGEN) is the Chloride salt form of Nicotinamide ribose (NR). NR is a derivative of vitamin B3 and acts as NAD or a precursor of NAD. NIAGEN is generally recognized in the United States as safe for use in food
Cell Line: HEK293T cells
Concentration: 0.5 nM
Incubation Time: 24 hours
Result: Reduced the acetylation status of Ndufa9 and SOD2.
Increased plasma and intracellular NAD + content in a tissue-specific manner.
Animal Model: 10-week-old C57Bl/6J mice
Dosage: 400 mg/kg
Administration: PO; daily; for 16 weeks
Last Update：2024-04-10 22:29:15
Nicotinamide riboside chloride
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