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
• Article Data: 14

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

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

Chemical Properties

Nicotinamide riboside (NR) is part of the B3 vitamin family. Like other forms of vitamin B3, nicotinamide riboside gets converted into nicotinamide adenine dinucleotide (NAD+), a coenzyme essential for life. For this reason, it is often called a NAD+ precursor because it is part of the series of chemical steps that are required to create NAD+.Different biosynthetic pathways are responsible for converting the different B3 vitamins into NAD+. The enzyme nicotinamide phosphoribosyltransferase (Nampt) catalyzes the rate-limiting step of the two-step pathway converting nicotinamide to NAD+. NR kinase enzymes can also function as a salvage pathway for NAD+, but this pathway is not essential.

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.

Definition

ChEBI: Nicotinamide riboside is a pyridine nucleoside consisting of nicotinamide with a beta-D-ribofuranosyl moiety at the 1-position. It is a metabolite found in or produced by Saccharomyces cerevisiae. It is an orally available form of vitamin B3 and precursor of nicotinamide adenine dinucleotide (NAD+) with potential use in the treatment of chemotherapy induced peripheral neuropathy (CIPN).

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

• 936945-09-4 2',3',5'-triacetyl ethyl nicotinate riboside 
• 53-84-9 NAD 
• 1094-61-7 nicotinamide mononucleotide 
• 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 

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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SummaryWhile mitochondrial dysfunction is emerging as key in Parkinson’s disease (PD), a central question remains whether mitochondria are actual disease drivers and whether boosting mitochondrial biogenesis and function ameliorates pathology. We address these questions using patient-derived in...detailed

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SummaryConditions of metabolic stress dysregulate the NAD metabolome. By restoring NAD, nicotinamide riboside (NR) provides resistance to such conditions. We tested the hypotheses that postpartum might dysregulate maternal NAD and that increasing systemic NAD with NR might benefit mothers and of...detailed

ArticleThe NAD-Booster NICOTINAMIDE RIBOSIDE (cas 1341-23-7) Potently Stimulates Hematopoiesis through Increased Mitochondrial Clearance09/05/2019

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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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Relevant articles and documents

Syntheses of nicotinamide riboside and derivatives: Effective agents for increasing nicotinamide adenine dinucleotide concentrations in mammalian cells

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

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

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