1341-23-7

Basic information

• Product Name: NICOTINAMIDE RIBOSIDE
• Synonyms: Nicotiamide Riboside;Nicotinamide ribonucleoside;NICOTINAMIDE RIBOSIDE(R)-5-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)cyclohexa-1,3-dienecarboxamide;NR(Nicotinamide Riboside);NICOTINAMIDE RIBOSIDE;Nicotinamide Ribose;1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyridine-5-carboxamide;nicotinamide-beta-riboside
• CAS NO: 1341-23-7
• Molecular Formula: C₁₁H₁₅N₂O₅
• Molecular Weight: 256.26
• EINECS: 1308068-626-2
• Mol File: 1341-23-7.mol

Chemical Properties

• Boiling Point: 646.2 °C at 760 mmHg
• Flash Point: 344.6 °C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 3.05E-07mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: NICOTINAMIDE RIBOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NICOTINAMIDE RIBOSIDE(1341-23-7)
• EPA Substance Registry System: NICOTINAMIDE RIBOSIDE(1341-23-7)

Safety Data

• Hazardous Substances Data: 1341-23-7(Hazardous Substances Data)

Usage

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

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)

Synthetic route

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

Conditions	Yield
Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose With hydrogen bromide; acetic acid In toluene at 0℃; for 2h; Stage #2: nicotinamide In toluene Stage #3: With ammonia In methanol at 0℃; Concentration;	86.8%

nicotinamide (98-92-0) + 1,2,3,5-tetraacetylribose (13035-61-5) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 1.5h; Stage #2: With methanol at 20℃; for 1h;
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 30 - 40℃; Large scale; Stage #2: With potassium carbonate In dichloromethane at 15℃; for 1h; Large scale;

2',3',5'-triacetyl ethyl nicotinate riboside trifluoroacetate → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With ammonium hydroxide In methanol at 4℃; for 16h;

2',3',5'-triacetyl ethyl nicotinate riboside → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With ammonia In methanol at 4℃; for 7h;
Stage #1: 2',3',5'-triacetyl ethyl nicotinate riboside With ammonia at -5 - 5℃; for 1h; Stage #2: With sodium ethanolate In ethanol at -5 - 5℃; for 1h;

NAD (53-84-9) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: zirconium(IV) chloride; water / 0.5 h / 80 °C 2: calcium L-ascorbate; water / 48 h / 80 °C View Scheme

nicotinamide mononucleotide (1094-61-7) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With water; calcium L-ascorbate at 80℃; for 48h; Reagent/catalyst;

5'-nicotinic acid ethyl ester ribose → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With ammonia In acetonitrile at -5 - 5℃; for 1h;

1-(2',3',5'-triacetyl-β-D-ribofuranosyl)nicotinamide → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With methanol at 25℃; for 0.5h; Large scale;	0.71 kg
With sodium ethanolate In ethanol at -5 - 5℃; for 1h;
With methanol; sodium methylate at -5 - 0℃; for 5h; Inert atmosphere;	8.5 g

nicotinamide riboside glycine → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) + glycine (56-40-6)

Conditions	Yield
In aq. buffer pH=7;

1,2,3,5-tetraacetylribose (13035-61-5) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: ammonia / 1 h / -5 - 5 °C 2.2: 1 h / -5 - 5 °C View Scheme
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: acetonitrile / 8 h / -5 °C / Inert atmosphere 2: sodium hydrogencarbonate; sodium hydroxide / water / 45 °C / Inert atmosphere 3: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 4: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme

3-pyridinecarboxylic acid ethyl ester (614-18-6) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2.1: ammonia / 1 h / -5 - 5 °C 2.2: 1 h / -5 - 5 °C View Scheme

nicotinamide (98-92-0) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 12 h / 0 - 20 °C 2: sodium ethanolate / ethanol / 1 h / -5 - 5 °C View Scheme
Multi-step reaction with 4 steps 1: acetonitrile / 8 h / -5 °C / Inert atmosphere 2: sodium hydrogencarbonate; sodium hydroxide / water / 45 °C / Inert atmosphere 3: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 4: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 0 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / water / 20 °C / Inert atmosphere 3: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 4: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

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

Conditions	Yield
With methanol; sodium methylate at -10 - 0℃; for 5h; Inert atmosphere;

C13H6F12O9 → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: dichloromethane / 10 h / 0 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / water / 20 °C / Inert atmosphere 3: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 4: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

CF3O3S(1-)*C17H12F9N2O8(1+) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium dithionite; potassium carbonate / water / 20 °C / Inert atmosphere 2: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 3: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

C17H13F9N2O8 → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium periodate / 1,4-dioxane / 20 °C / Inert atmosphere 2: sodium methylate; methanol / 8 h / -10 - 0 °C / Inert atmosphere View Scheme

C17H12F9N2O8(1+) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With methanol; sodium methylate at -10 - 0℃; for 8h; Inert atmosphere;

C32H24N5O14(1+) → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
With methanol; sodium methylate at -10 - 0℃; for 3h; Inert atmosphere;

3-carbamoyl-1-((2R,3R,4R,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium trifluoromethanesulfonate → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate; sodium hydroxide / water / 45 °C / Inert atmosphere 2: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 3: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme

[(2R,5R)-3,4-diacetoxy-5-(3-carbamoyl-4H-pyridin-1-yl)tetrahydrofuran-2-yl]methyl acetate → 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: chloranil / tetrahydrofuran / 0 °C / Inert atmosphere 2: sodium methylate; methanol / 5 h / -5 - 0 °C / Inert atmosphere View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → 1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide (19132-12-8)

Conditions	Yield
With dipotassium hydrogenphosphate; sodium dithionite at 0℃; for 0.5h; pH=8; Inert atmosphere;	70%

malic acid (617-48-1) + 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C11H15N2O5(1+)*C4H5O5(1-)*C4H6O5

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	60.51%

malic acid (617-48-1) + 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → nicotinamide ribose malate

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	60.51%

malic acid (617-48-1) + 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C11H15N2O5(1+)*C4H5O5(1-)

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	57%

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) + citric acid (77-92-9) → C11H15N2O5(1+)*C6H8O7*C6H7O7(1-)

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	56.82%

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) + citric acid (77-92-9) → nicotinamide ribose citrate

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	56.82%

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → nicotinamide mononucleotide (1094-61-7)

Conditions	Yield
With trichlorophosphate In tetrahydrofuran at 0 - 20℃; for 12h;	56%

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) + citric acid (77-92-9) → C11H15N2O5(1+)*C6H7O7(1-)

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	55.91%

10-hydroxy-2-decenoic acid (765-01-5) + 1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C11H15N2O5(1+)*C10H17O3(1-)*C10H18O3

Conditions	Yield
In methanol at -10 - -5℃; for 2h; Inert atmosphere;	50%

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → nicotinamide (98-92-0)

Conditions	Yield
With potassium hydroxide; CAPS buffer (pH > 7); potassium chloride In water at 37℃; Product distribution; Mechanism; Kinetics;
With human CD157; water In aq. phosphate buffer pH=7; Kinetics; Enzymatic reaction;

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

Conditions	Yield
With trichlorophosphate In various solvent(s) at 0℃; for 4h;
With human nicotinamide riboside kinase-1; ATP; magnesium chloride at 37℃; for 2h; pH=7.5; aq. phosphate buffer; Enzymatic reaction;

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → imidazolide nicotinamide monophosphate (938173-81-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C28H35N7O17P3(1+)

Conditions	Yield
Multi-step reaction with 4 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C 4: 22 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 0 °C View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → (C3H7)4Si2OOH(C10H10N5O4)(PO(OC7H7)2)(POOH)O(H2NCOC5H3NC5O4H9POOH)(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → nicotinamide adenine dinucleotide phosphate (604-79-5)

Conditions	Yield
Multi-step reaction with 5 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C 4: 22 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 0 °C 5: 77 percent / cyclohexadiene / Pd/C / methanol; H2O / 2 h / 20 °C View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → 1-[(2R,3R,4S,5R)-5-[[[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxyhydroxyphosphoryl]oxyhydroxyphosphoryl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyridin-1-ium-3-carboxylic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: POCl3 / various solvent(s) / 4 h / 0 °C 2: Et3N / dimethylformamide / 3 h / 20 °C 3: dimethylformamide / 24 h / 20 °C 4: 22 percent / TBAF; AcOH / tetrahydrofuran / 3 h / 0 °C 5: 77 percent / cyclohexadiene / Pd/C / methanol; H2O / 2 h / 20 °C 6: 63 percent / aq. NaOAc / Aplysia ADP-ribosyl cyclase / 5 h / 20 °C / pH 4 View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) + ATP (56-65-5) → nicotinamide adenine dinucleotide (865-05-4)

Conditions	Yield
With human nicotinamide mononucleotide adenylyltransferase 1; human nicotinamide riboside kinase 1 at 20℃; for 4h; Enzymatic reaction;

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → α-D-ribofuranosyl-1-phosphate + nicotinamide (98-92-0)

Conditions	Yield
With potassium dihydrogenphosphate; purine nucleoside phosphorylase In aq. buffer pH=7; Enzymatic reaction;

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C4H5O5(1-)*C4H6O5*(x)C6H4NO2(1-)*C11H15N2O5(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / -10 - -5 °C / Inert atmosphere 2: 0.17 h / 16 °C / Inert atmosphere View Scheme

1-(β-D-ribofuranosyl)-nicotinamide (1341-23-7) → C4H5O5(1-)*C4H6O5*(x)C5H8NO4(1-)*C11H15N2O5(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 2 h / -10 - -5 °C / Inert atmosphere 2: 0.17 h / Inert atmosphere View Scheme

Upstream product

• 69216-50-8 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-carbamoyl-pyridinium 
• 98-92-0 nicotinamide 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 1094-61-7 nicotinamide mononucleotide 
• 53-84-9 NAD 
• 936945-09-4 2',3',5'-triacetyl ethyl nicotinate riboside 

Downstream Products

• 98-92-0 nicotinamide 
• 1094-61-7 nicotinamide mononucleotide 
• 36468-53-8 β-D-ribofuranose 
• 23111-00-4 3-carbamoyl-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyridin-1-ium (β-D-nicotinamide riboside) 
• 19132-12-8 1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-1,4-dihydropyridine-3-carboxamide 

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Original ArticleNICOTINAMIDE RIBOSIDE (cas 1341-23-7) kinases display redundancy in mediating nicotinamide mononucleotide and NICOTINAMIDE RIBOSIDE (cas 1341-23-7) metabolism in skeletal muscle cells09/01/2019

ObjectiveAugmenting nicotinamide adenine dinucleotide (NAD+) availability may protect skeletal muscle from age-related metabolic decline. Dietary supplementation of NAD+ precursors nicotinamide mononucleotide (NMN) and nicotinamide riboside (NR) appear efficacious in elevating muscle NAD+. Here ...detailed

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The present invention relates to Nicotinamide mononucleotide derivatives of formula (I) or (Ia) for use in the treatment and/or prevention of viral infections, such as respiratory infections. The present invention further relates to pharmaceutical composi

Β - nicotinamide mononucleotide preparation method

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.

Preparation method of nicotinamide ribose, reduction state and salt of nicotinamide ribose

The invention belongs to the technical field of organic synthesis. The invention discloses a preparation method of nicotinamide ribose. The method comprises the following steps: reacting an intermediate A with nicotinamide in the presence of TMSOTf to obt

Process preparation method of beta-nicotinamide mononucleotide

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.

Nicotinamide riboside-amino acid conjugates that are stable to purine nucleoside phosphorylase

The nutraceutical Nicotinamide Riboside (NR), an efficacious biosynthetic precursor to NAD, is readily metabolized by the purine nucleoside phosphorylase (PNP). Access to the PNP-stable versions of NR is difficult because the glycosidic bond of NR is easily cleaved. Unlike NR, NRH, the reduced form of NR, offers sufficient chemical stability to allow the successful functionalisation of the ribosyl-moiety. Here, we report on a series of NRH and NR derived amino acid conjugates, generated in good to excellent yields and show that O5′-esterification prevents the PNP-catalyzed phosphorolysis of these NR prodrugs.

Crystal form 1A and crystal form 1B of beta-nicotinamide ribose chloride and preparation method of crystal form 1A and crystal form 1B

The invention discloses a crystal form 1A and a crystal form 1B of beta-nicotinamide ribose chloride and preparation methods of the crystal form 1A and the crystal form 1B. In an X-ray powder diffraction pattern, the crystal form 1A has diffraction peaks with 2 theta of 13.0+/-0.2 degrees, 14.0+/-0.2 degrees, 23.8+/-0.2 degrees, 24.5+/-0.2 degrees and 25.4+/-0.2 degrees. In an X-ray powder diffraction pattern, the crystal form 1B has diffraction peaks with 2 theta of 5.0+/-0.2 degrees, 15.6+/-0.2 degrees, 21.6+/-0.2 degrees and 26.4+/-0.2 degrees. These two crystal forms of nicotinamide ribosehave more advantageous properties including substance morphology, stability (e.g., low content of solvent residue, low hygroscopicity, storage stability, polymorph transformation stability), solubility, chemical purity, and the like. The change of the properties is more beneficial to industrial production of high-purity nicotinamide ribose, and a wide space is provided for development of dosage forms of nicotinamide ribose.

Preparation method of nicotinamide ribose

The invention relates to a preparation method of nicotinamide ribose. The method comprises the steps that nicotinamide and 1,2,3,5-tetraacethyl-beta-D-ribofuranose serve as a synthetic starting material, and a finished nicotinamide ribose product is obtai