Nicotinamide Riboside Chloride NRC

What is NRC?

NRC (Nicotinamide Riboside Chloride) is a precursor compound of nicotinamide adenine dinucleotide (NAD+) and nicotinamide adenine dinucleotide phosphate (NADP+). These compounds play key roles in cells, including participating in energy metabolism, DNA repair, signal transduction, etc. They can be used to study these biological processes and participate in certain enzyme catalytic reactions as coenzymes. It has been implicated in increasing tissue NAD concentrations and inducing insulin sensitivity and enhancing sirtuin function. Its ability to increase NAD production suggests that it can also improve mitochondrial health, stimulate mitochondrial function, and induce the production of new mitochondria. Other studies using nicotinamide riboside in Alzheimer's disease models have shown that the molecule is bioavailable to the brain and may provide neuroprotection by stimulating brain NAD synthesis.

Main effects and functions:

1. Anti-inflammatory effect
As a derivative of vitamin B3, it has a significant anti-inflammatory effect. It can reduce inflammatory responses
2. Increase NAD+ levels
It can increase the level of NAD+, which is a key coenzyme for maintaining cell function and energy metabolism. By increasing NAD+, it helps to improve mitochondrial health, stimulate mitochondrial function, and induce the production of new mitochondria.
3. Improve metabolic function
Studies have shown that it can improve mitochondrial function in muscle stem cells of aged mice and correct the non-choline fatty liver phenotype induced by NAD+ deficiency or high-fat diet in mice. In addition, it can improve insulin sensitivity and enhance the function of sirtuins.
4. Neuroprotective effect
Studies in Alzheimer's disease models have shown that it is bioavailable to the brain and may provide neuroprotection by stimulating brain NAD synthesis.
5. Anti-aging potential
By increasing NAD+ levels, SIRT1 and SIRT3 are activated, ultimately enhancing oxidative metabolism and protecting it from metabolic abnormalities caused by a high-fat diet. This mechanism gives it a potential anti-aging advantage.

Application areas:

1. Pharmaceutical intermediates
As an important pharmaceutical intermediate, it is widely used in drug development and production processes.
2. Nutritional supplements
Due to its multiple benefits to human health,, is also used as a dietary supplement to help improve metabolism and delay aging.

Production method:
The residue was transferred back to the 20L reactor with 7.5L 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 dissolved 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 1.25 L (3.75 mol) of 3M HCl was slowly added, 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 can be stored at 4°C for up to 48 h). After the concentration was complete, the residue could be stored at -20°C for up to 18 h. To remove residual methanol, the evaporation residue was dissolved in water and concentrated under vacuum (3x1 L). The residue was taken up in 5 L 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 5 g of undissolved NaCl.
The saturated solution was extracted with tetrahydrofuran (THF, 3x5 L). The aqueous layer was monitored by 1HNMR 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 (4x5 L). The aqueous layer was monitored by 1H NMR to confirm that the residual nicotinamide was <5 mol% relative to 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 2.5 L of water. The residual suspension was diluted with 5 L of ethanol, filtered, and the salt precipitate was washed with 2.5 L of ethanol. The combined filtrate and washings were concentrated under vacuum to a viscous oil. This was stirred with 1.5 L of methanol, the precipitate was filtered, and the solution was concentrated under vacuum. Another 1.5 L of methanol was stirred with the residue, the precipitate was filtered, and the solution was concentrated under vacuum. The residue was stirred with a third 1.5 L of methanol, the precipitate was filtered, and the solution was concentrated under vacuum to obtain 385 g of an orange-red oil. The amount of residual methanol was confirmed to be 34 g by 1H NMR, and the crude product yield was 351 g (77%). THF extraction was used to remove most of the excess nicotinamide.

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