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MedKoo Cat#: 564087 | Name: Nicotinamide Riboside Triflate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nicotinamide Riboside is a precursor of NAD+ and a source of vitamin B3 (niacin). Nicotinamide Riboside increases intracellular and mitochondrial NAD+ content in C2C12.

Chemical Structure

Nicotinamide Riboside Triflate
CAS#445489-49-6 (Triflate)

Theoretical Analysis

MedKoo Cat#: 564087

Name: Nicotinamide Riboside Triflate

CAS#: 445489-49-6 (Triflate)

Chemical Formula: C12H15F3N2O8S

Exact Mass: 0.0000

Molecular Weight: 404.31

Elemental Analysis: C, 35.65; H, 3.74; F, 14.10; N, 6.93; O, 31.66; S, 7.93

Price and Availability

Size Price Availability Quantity
1mg USD 150.00 Ready to ship
2mg USD 250.00 Ready to ship
5mg USD 550.00 Ready to ship
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Related CAS #
1341-23-7 (cation) 23111-00-4 (chloride) 445489-49-6 (Triflate)
Synonym
SRT647; SRT-647; SRT 647; Nicotinamide Ribose; Nicotinamide Riboside; Nicotinamide Riboside Triflate; Nicotinamide Ribonucleoside Triflate; NAR; Ribosylnicotinamide Triflate
IUPAC/Chemical Name
3-(Aminocarbonyl)-1-B-D-ribofuranosyl-pyridinium Trifluoromethanesulfonic Acid
InChi Key
ZEWRNTDQENDMQK-IVOJBTPCSA-N
InChi Code
InChI=1S/C11H14N2O5.CHF3O3S/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11;2-1(3,4)8(5,6)7/h1-4,7-9,11,14-16H,5H2,(H-,12,17);(H,5,6,7)/t7-,8-,9-,11-;/m1./s1
SMILES Code
O[C@H]1[C@H]([N+]2=CC=CC(C(N)=O)=C2)O[C@H](CO)[C@H]1O.O=S(C(F)(F)F)([O-])=O
Appearance
Solid powder
Purity
>87% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C9B11S20
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Nicotinamide riboside, also known as NR and SRT647, is a pyridine-nucleoside form of vitamin B3 that prevents muscle, neural and melanocyte stem cell senescence
In vitro activity:
In in vitro experiments, HepG2 cells (CYP2E1 over-expressing cells) were incubated with ethanol ± 0.5 mmol/L NR (nicotinamide riboside). Lipid accumulation and mitochondrial function were compared. Ethanol decreased the levels of NAD+ and ATP in HepG2 cells, which were upregulated by NR (Fig. 5A). The oxygen consumption rate (OCR) in HepG2 cells was abolished by ethanol. The basal OCR and reserve oxidative capacity, which is the FCCP-sensitive OCR, and respiratory capacity, which is the rotenone sensitive OCR, were all decreased by ethanol. These changes were reversed by NR, indicating that NR improved mitochondrial aerobic respiration (Fig. 5B, S5A). Next, a reduction in mtDNA abundance by ethanol was detected and NR increased the mtDNA copies (Fig. 5C). Consistently, the estrogen-related receptor α (ERRα), which mediates many of the downstream effects of PGC-1α on mitochondrial biosynthesis and energy metabolism, was markedly decreased by ethanol, as was the ERRα/PGC-1α target, nuclear respiratory factor-1 (NRF1) and its target, mitochondrial transcription factor A (TFAM), and nuclear respiratory factor-2 (NRF2). NR increased the expressions of ERRα, NRF1, NRF2 and TFAM, promoting mitochondrial biogenesis (Fig. 5D). Reference: Redox Biol. 2018 Jul; 17: 89–98. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6007172/
In vivo activity:
This study aimed to explore the effect of NR (nicotinamide riboside) on ethanol induced liver injuries and the underlying mechanisms. We fed C57BL/6 J mice with Lieber-DeCarli ethanol liquid diet with or without 400 mg/kg·bw NR for 16 days. Liver injuries and SirT1-PGC-1α-mitochondrial function were analyzed. Mice were pair-fed and there were no differences in body weight among the three groups (Fig. S1A, B). Fat accumulated in ethanol group, but only a small number of tiny lipid droplets were observed in NR treated mice as shown in H&E staining and Oil red O staining (Fig. 1A). Ethanol exposure elevated serum ALT and AST and liver triglycerides while NR significantly decreased their levels (Fig. 1B, C). The ratio of liver-to-body weight increased by ethanol compared to controls, while it was slightly reduced by NR (Fig. S1C). The expressions of sterol regulatory element binding protein-lc (SREBP-1c) and peroxisome proliferator-activated receptorγ2 (PPAR-γ2), as well as PPAR-γ mRNA, were markedly elevated by ethanol, which were reduced by NR (Fig. 1D, S1D). Ethanol increased the levels of hepatic MDA and 4-hydroxynonenal, two major products of lipid peroxidation, and NR markedly decreased them (Fig. 1C, D). SirT1 was significantly decreased in liver of ethanol fed mice compared to controls, and NR restored SirT1 to normal (Fig. 1D). There was also a decrease in the hepatic inflammatory transcripts TNF-α and IL-6 in NR-treated mice compared to mice of ethanol group (Fig. S1D). Reference: Redox Biol. 2018 Jul; 17: 89–98. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6007172/

Preparing Stock Solutions

The following data is based on the product molecular weight 404.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wang S, Wan T, Ye M, Qiu Y, Pei L, Jiang R, Pang N, Huang Y, Liang B, Ling W, Lin X, Zhang Z, Yang L. Nicotinamide riboside attenuates alcohol induced liver injuries via activation of SirT1/PGC-1α/mitochondrial biosynthesis pathway. Redox Biol. 2018 Jul;17:89-98. doi: 10.1016/j.redox.2018.04.006. Epub 2018 Apr 5. PMID: 29679894; PMCID: PMC6007172. 2. Godek CP, Cynamon MH. In vitro evaluation of nicotinamide riboside analogs against Haemophilus influenzae. Antimicrob Agents Chemother. 1990 Aug;34(8):1473-9. doi: 10.1128/AAC.34.8.1473. PMID: 2145800; PMCID: PMC171855. 3. Diguet N, Trammell SAJ, Tannous C, Deloux R, Piquereau J, Mougenot N, Gouge A, Gressette M, Manoury B, Blanc J, Breton M, Decaux JF, Lavery GG, Baczkó I, Zoll J, Garnier A, Li Z, Brenner C, Mericskay M. Nicotinamide Riboside Preserves Cardiac Function in a Mouse Model of Dilated Cardiomyopathy. Circulation. 2018 May 22;137(21):2256-2273. doi: 10.1161/CIRCULATIONAHA.116.026099. Epub 2017 Dec 7. Erratum in: Circulation. 2018 May 22;137(21):e690. PMID: 29217642; PMCID: PMC6954688.
In vitro protocol:
1. Wang S, Wan T, Ye M, Qiu Y, Pei L, Jiang R, Pang N, Huang Y, Liang B, Ling W, Lin X, Zhang Z, Yang L. Nicotinamide riboside attenuates alcohol induced liver injuries via activation of SirT1/PGC-1α/mitochondrial biosynthesis pathway. Redox Biol. 2018 Jul;17:89-98. doi: 10.1016/j.redox.2018.04.006. Epub 2018 Apr 5. PMID: 29679894; PMCID: PMC6007172. 2. Godek CP, Cynamon MH. In vitro evaluation of nicotinamide riboside analogs against Haemophilus influenzae. Antimicrob Agents Chemother. 1990 Aug;34(8):1473-9. doi: 10.1128/AAC.34.8.1473. PMID: 2145800; PMCID: PMC171855.
In vivo protocol:
1. Wang S, Wan T, Ye M, Qiu Y, Pei L, Jiang R, Pang N, Huang Y, Liang B, Ling W, Lin X, Zhang Z, Yang L. Nicotinamide riboside attenuates alcohol induced liver injuries via activation of SirT1/PGC-1α/mitochondrial biosynthesis pathway. Redox Biol. 2018 Jul;17:89-98. doi: 10.1016/j.redox.2018.04.006. Epub 2018 Apr 5. PMID: 29679894; PMCID: PMC6007172. 2. Diguet N, Trammell SAJ, Tannous C, Deloux R, Piquereau J, Mougenot N, Gouge A, Gressette M, Manoury B, Blanc J, Breton M, Decaux JF, Lavery GG, Baczkó I, Zoll J, Garnier A, Li Z, Brenner C, Mericskay M. Nicotinamide Riboside Preserves Cardiac Function in a Mouse Model of Dilated Cardiomyopathy. Circulation. 2018 May 22;137(21):2256-2273. doi: 10.1161/CIRCULATIONAHA.116.026099. Epub 2017 Dec 7. Erratum in: Circulation. 2018 May 22;137(21):e690. PMID: 29217642; PMCID: PMC6954688.
1: Crisol BM, Veiga CB, Lenhare L, Braga RR, Silva VRR, da Silva ASR, Cintra DE, Moura LP, Pauli JR, Ropelle ER. Nicotinamide riboside induces a thermogenic response in lean mice. Life Sci. 2018 Sep 6. pii: S0024-3205(18)30560-5. doi: 10.1016/j.lfs.2018.09.015. [Epub ahead of print] PubMed PMID: 30195617. 2: Dellinger RW, Santos SR, Morris M, Evans M, Alminana D, Guarente L, Marcotulli E. Erratum: Author Correction: Repeat dose NRPT (nicotinamide riboside and pterostilbene) increases NAD(+) levels in humans safely and sustainably: a randomized, double-blind, placebo-controlled study. NPJ Aging Mech Dis. 2018 Aug 20;4:8. doi: 10.1038/s41514-018-0027-1. eCollection 2018. PubMed PMID: 30155270; PubMed Central PMCID: PMC6102308. 3: Serrano A, Asnani-Kishnani M, Rodríguez AM, Palou A, Ribot J, Bonet ML. Programming of the Beige Phenotype in White Adipose Tissue of Adult Mice by Mild Resveratrol and Nicotinamide Riboside Supplementations in Early Postnatal Life. Mol Nutr Food Res. 2018 Aug 10:e1800463. doi: 10.1002/mnfr.201800463. [Epub ahead of print] PubMed PMID: 30095217. 4: Kourtzidis IA, Dolopikou CF, Tsiftsis AN, Margaritelis NV, Theodorou AA, Zervos IA, Tsantarliotou MP, Veskoukis AS, Vrabas IS, Paschalis V, Kyparos A, Nikolaidis MG. Nicotinamide riboside supplementation dysregulates redox and energy metabolism in rats: Implications for exercise performance. Exp Physiol. 2018 Oct;103(10):1357-1366. doi: 10.1113/EP086964. Epub 2018 Aug 28. PubMed PMID: 30007015. 5: Dollerup OL, Christensen B, Svart M, Schmidt MS, Sulek K, Ringgaard S, Stødkilde-Jørgensen H, Møller N, Brenner C, Treebak JT, Jessen N. A randomized placebo-controlled clinical trial of nicotinamide riboside in obese men: safety, insulin-sensitivity, and lipid-mobilizing effects. Am J Clin Nutr. 2018 Aug 1;108(2):343-353. doi: 10.1093/ajcn/nqy132. PubMed PMID: 29992272. 6: Schöndorf DC, Ivanyuk D, Baden P, Sanchez-Martinez A, De Cicco S, Yu C, Giunta I, Schwarz LK, Di Napoli G, Panagiotakopoulou V, Nestel S, Keatinge M, Pruszak J, Bandmann O, Heimrich B, Gasser T, Whitworth AJ, Deleidi M. The NAD+ Precursor Nicotinamide Riboside Rescues Mitochondrial Defects and Neuronal Loss in iPSC and Fly Models of Parkinson's Disease. Cell Rep. 2018 Jun 5;23(10):2976-2988. doi: 10.1016/j.celrep.2018.05.009. PubMed PMID: 29874584. 7: Fletcher RS, Lavery G. The Emergence of the Nicotinamide Riboside Kinases in the regulation of NAD+ Metabolism. J Mol Endocrinol. 2018 May 30. pii: JME-18-0085. doi: 10.1530/JME-18-0085. [Epub ahead of print] PubMed PMID: 29848626; PubMed Central PMCID: PMC6145238. 8: Hong G, Zheng D, Zhang L, Ni R, Wang G, Fan GC, Lu Z, Peng T. Administration of nicotinamide riboside prevents oxidative stress and organ injury in sepsis. Free Radic Biol Med. 2018 Aug 1;123:125-137. doi: 10.1016/j.freeradbiomed.2018.05.073. Epub 2018 May 24. PubMed PMID: 29803807. 9: Correction to: Nicotinamide Riboside Preserves Cardiac Function in a Mouse Model of Dilated Cardiomyopathy. Circulation. 2018 May 22;137(21):e690. doi: 10.1161/CIR.0000000000000581. PubMed PMID: 29784693. 10: Tran A, Yokose R, Cen Y. Chemo-enzymatic synthesis of isotopically labeled nicotinamide riboside. Org Biomol Chem. 2018 May 15;16(19):3662-3671. doi: 10.1039/c8ob00552d. PubMed PMID: 29714801; PubMed Central PMCID: PMC6054311. 11: Wang S, Wan T, Ye M, Qiu Y, Pei L, Jiang R, Pang N, Huang Y, Liang B, Ling W, Lin X, Zhang Z, Yang L. Nicotinamide riboside attenuates alcohol induced liver injuries via activation of SirT1/PGC-1α/mitochondrial biosynthesis pathway. Redox Biol. 2018 Jul;17:89-98. doi: 10.1016/j.redox.2018.04.006. Epub 2018 Apr 5. PubMed PMID: 29679894; PubMed Central PMCID: PMC6007172. 12: Martens CR, Denman BA, Mazzo MR, Armstrong ML, Reisdorph N, McQueen MB, Chonchol M, Seals DR. Chronic nicotinamide riboside supplementation is well-tolerated and elevates NAD(+) in healthy middle-aged and older adults. Nat Commun. 2018 Mar 29;9(1):1286. doi: 10.1038/s41467-018-03421-7. PubMed PMID: 29599478; PubMed Central PMCID: PMC5876407. 13: Zhang N, Sauve AA. Synthesis of β-Nicotinamide Riboside Using an Efficient Two-Step Methodology. Curr Protoc Nucleic Acid Chem. 2017 Dec 24;71:14.14.1-14.14.9. doi: 10.1002/cpnc.43. PubMed PMID: 29275540; PubMed Central PMCID: PMC5965287. 14: Diguet N, Trammell SAJ, Tannous C, Deloux R, Piquereau J, Mougenot N, Gouge A, Gressette M, Manoury B, Blanc J, Breton M, Decaux JF, Lavery GG, Baczkó I, Zoll J, Garnier A, Li Z, Brenner C, Mericskay M. Nicotinamide Riboside Preserves Cardiac Function in a Mouse Model of Dilated Cardiomyopathy. Circulation. 2018 May 22;137(21):2256-2273. doi: 10.1161/CIRCULATIONAHA.116.026099. Epub 2017 Dec 7. Erratum in: Circulation. 2018 May 22;137(21):e690. PubMed PMID: 29217642. 15: Airhart SE, Shireman LM, Risler LJ, Anderson GD, Nagana Gowda GA, Raftery D, Tian R, Shen DD, O'Brien KD. An open-label, non-randomized study of the pharmacokinetics of the nutritional supplement nicotinamide riboside (NR) and its effects on blood NAD+ levels in healthy volunteers. PLoS One. 2017 Dec 6;12(12):e0186459. doi: 10.1371/journal.pone.0186459. eCollection 2017. PubMed PMID: 29211728; PubMed Central PMCID: PMC5718430. 16: Dellinger RW, Santos SR, Morris M, Evans M, Alminana D, Guarente L, Marcotulli E. Repeat dose NRPT (nicotinamide riboside and pterostilbene) increases NAD(+) levels in humans safely and sustainably: a randomized, double-blind, placebo-controlled study. NPJ Aging Mech Dis. 2017 Nov 24;3:17. doi: 10.1038/s41514-017-0016-9. eCollection 2017. Erratum in: NPJ Aging Mech Dis. 2018 Aug 20;4:8. PubMed PMID: 29184669; PubMed Central PMCID: PMC5701244. 17: Vaur P, Brugg B, Mericskay M, Li Z, Schmidt MS, Vivien D, Orset C, Jacotot E, Brenner C, Duplus E. Nicotinamide riboside, a form of vitamin B(3), protects against excitotoxicity-induced axonal degeneration. FASEB J. 2017 Dec;31(12):5440-5452. doi: 10.1096/fj.201700221RR. Epub 2017 Aug 21. PubMed PMID: 28842432. 18: Fletcher RS, Ratajczak J, Doig CL, Oakey LA, Callingham R, Da Silva Xavier G, Garten A, Elhassan YS, Redpath P, Migaud ME, Philp A, Brenner C, Canto C, Lavery GG. Nicotinamide riboside kinases display redundancy in mediating nicotinamide mononucleotide and nicotinamide riboside metabolism in skeletal muscle cells. Mol Metab. 2017 May 29;6(8):819-832. doi: 10.1016/j.molmet.2017.05.011. eCollection 2017 Aug. PubMed PMID: 28752046; PubMed Central PMCID: PMC5518663. 19: Teijeiro A, Djouder N. Nicotinamide riboside or IL-17A signaling blockers to prevent liver disorders. Oncoscience. 2017 Feb 24;4(1-2):1-2. doi: 10.18632/oncoscience.338. eCollection 2017 Jan. PubMed PMID: 28484725; PubMed Central PMCID: PMC5361639. 20: Hamity MV, White SR, Walder RY, Schmidt MS, Brenner C, Hammond DL. Nicotinamide riboside, a form of vitamin B3 and NAD+ precursor, relieves the nociceptive and aversive dimensions of paclitaxel-induced peripheral neuropathy in female rats. Pain. 2017 May;158(5):962-972. doi: 10.1097/j.pain.0000000000000862. PubMed PMID: 28346814.