Nicotinamide riboside

Base Information

• Chemical Name: Nicotinamide riboside
• CAS No.: 1341-23-7
• Molecular Formula: C11H15 N2 O5
• Molecular Weight: 255.25
• European Community (EC) Number: 811-511-0
• UNII: 0I8H2M0L7N
• DSSTox Substance ID: DTXSID501010039
• Nikkaji Number: J490.568G
• Wikipedia: Nicotinamide_riboside
• Wikidata: Q3334152
• NCI Thesaurus Code: C158078
• Metabolomics Workbench ID: 37466
• ChEMBL ID: CHEMBL438497
• Mol file: 1341-23-7.mol

Synonyms:Niagen;nicotinamide ribonucleoside;nicotinamide ribose;nicotinamide riboside;nicotinamide-beta-riboside;pyridinium, 3-(aminocarbonyl)-1-beta-D-ribofuranosyl-;ribosylnicotinamide;SRT 647;SRT-647;SRT647;TruNiagen

Chemical Property of Nicotinamide riboside

Chemical Property:

• Vapor Pressure: 3.05E-07mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 646.2 °C at 760 mmHg
• Flash Point: 344.6 °C
• PSA: 116.25000
• Density: 1.201g/cm³
• LogP: -1.69540
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 255.09809658
• Heavy Atom Count: 18
• Complexity: 314

Purity/Quality:

NicotinamideRiboside ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C[N+](=C1)C2C(C(C(O2)CO)O)O)C(=O)N
• Isomeric SMILES: C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
• Recent ClinicalTrials: The Effect of NAD Supplementation on Brain Vascular Health in Aging
• Recent NIPH Clinical Trials: Cross-over trial to verify safety and effectiveness of nicotinamide riboside for patients with Werner syndrome
• Description: Nicotinamide Riboside (NR) is a next-generation vitamin B3 that has been found to be naturally-occurring in milk in trace amounts. The metabolism of NR is unique from that of other more commonly known forms of vitamin B3 , nicotinamide and nicotinic acid. Specifically, NR has been shown in a pre-clinical study to be the most effective form of vitamin B3 at increasing nicotinamide adenine dinucleotide (NAD+)2 .Nicotinic acid (also known as niacin) and nicotinamide (also known as niacinamide) were discovered in the 1930’s to be the factors that cured pellagra . Niacin is known to cause severe flushing . In 2004, nicotinamide riboside emerged as a newly discovered NAD+ precursor and does not bind to the receptor responsible for flushing.NR has pre-clinically demonstrated that it is superior to both niacin and nicotinamide, both of which are standard forms of vitamin B3 commonly used in vitamin supplements and foods, at boosting NAD+2 . This is due to the fact that NR is not reliant upon a conversion step requiring the enzyme “NAMPT” , see Figure below. The activity level of NAMPT determines the amount of nicotinamide that is converted into NAD+ , which is why this particular step in the process is often referred to as the “rate limiting step”. As normal aging occurs, the activity of NAMPT is thought to decrease. NR can be used by the cell to make NAD+ without this enzymatic step.NAD+ synthesis from nicotinic acid, nicotinamide, and nicotinamide riboside
• Uses: Nicotinamide Riboside can be used in biological study of gene circadian reprogramming transcriptome in liver identified metabolic pathways of aging in mouse. It also increases NAD+ in the cerebral cortex and reduces cognitive deterioration in a transgenic mouse model of Alzheimer’s disease.
• 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.

Technology Process of Nicotinamide riboside

There total 21 articles about Nicotinamide riboside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.6%

1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-carbamoyl-pyridinium (69216-50-8) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Guidance literature:

With triethylamine; In ethanol; at -5 - 35 ℃; for 4.5h; Reagent/catalyst;

Reference yield: 86.8%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose + nicotinamide (98-92-0,1255150-40-3) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Guidance literature:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; With hydrogen bromide; acetic acid; In toluene; at 0 ℃; for 2h;

nicotinamide; In toluene;

With ammonia; In methanol; at 0 ℃; Concentration;

Reference yield:

→ 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Guidance literature:

NMN⁺ (oxyd. Nicotinamid-mononucleotid), enzymatische Bldg.;

upstream raw materials:

nicotinamide

1,2,3,5-tetraacetylribose

2',3',5'-triacetyl ethyl nicotinate riboside

NAD

Downstream raw materials:

nicotinamide

nicotinamide mononucleotide

β-D-ribofuranose

3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside)

Refernces

• 1、 Garavaglia, Silvia,Bruzzone, Santina,Cassani, Camilla,Canella, Laura,Allegrone, Gianna,Sturla, Laura,Mannino, Elena,Millo, Enrico,De Flora, Antonio,Rizzi, Menico. "The high-resolution crystal structure of periplasmic Haemophilus influenzae NAD nucleotidase reveals a novel enzymatic function of human CD73 related to NAD metabolism". . p. 131 - 141. Retrieved 2012.
• 2、 -. "NICOTINAMIDE MONONUCLEOTIDE AND NICOTINAMIDE RIBOSIDE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF VIRAL INFECTIONS AND RESPIRATORY COMPLICATIONS, IN PARTICULAR CAUSED BY INFLUENZAVIRUS OR CORONAVIRUS". Page/Page column 66; 67. . Retrieved 2021/10/30.
• 3、 -. "Crystal form 1A and crystal form 1B of beta-nicotinamide ribose chloride and preparation method of crystal form 1A and crystal form 1B". Paragraph 0056-0060; 0074-0077. . Retrieved 2020/11/02.