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MedKoo Cat#: 464819 | Name: Nicotinamide-d4
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Description:

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

Nicotinamide-d4 is intended for use as an internal standard for the quantification of nicotinamide by GC- or LC-MS. Nicotinamide is an amide form of niacin, which is also known as vitamin B3, that can be biosynthesized in vivo or obtained through the diet. It is a precursor in the synthesis of the metabolic cofactor NAD+ and an inhibitor of sirtuin 1 (SIRT1; IC50 = <50 µM). Nicotinamide (10 µM) increases the activity of serine palmitoyltransferase (SPT) and the biosynthesis of ceramide, glucosylceramide, sphingomyelin, free fatty acids, and cholesterol in primary human keratinocytes. Nicotinamide (40 µM) induces apoptosis in SNU-398, SNU-739, and HepG2 hepatocellular carcinoma (HCC) cells, and it prevents the formation of neoplastic lesions in a diethylnitrosamine-induced mouse model of HCC. Unlike niacin, nicotinamide does not reduce plasma lipid levels or induce flushing.

Chemical Structure

Nicotinamide-d4
Nicotinamide-d4
CAS#347841-88-7

Theoretical Analysis

MedKoo Cat#: 464819

Name: Nicotinamide-d4

CAS#: 347841-88-7

Chemical Formula: C6H2D4N2O

Exact Mass: 126.0731

Molecular Weight: 126.15

Elemental Analysis: C, 57.13; H, 7.98; N, 22.21; O, 12.68

Price and Availability

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5mg USD 550.00 2 Weeks
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Synonym
Nicotinamide-d4; Nicotinamide d4; Niacinamide-d4; Niacinamide d4; Nicotinic Acid Amide-d4; Nicotinic Acid Amide d4; Vitamin B3 Amide-d4; Vitamin B3 Amide d4;
IUPAC/Chemical Name
nicotinamide-2,4,5,6-d4
InChi Key
DFPAKSUCGFBDDF-RHQRLBAQSA-N
InChi Code
InChI=1S/C6H6N2O/c7-6(9)5-2-1-3-8-4-5/h1-4H,(H2,7,9)/i1D,2D,3D,4D
SMILES Code
NC(C1=C(N=C(C([2H])=C1[2H])[2H])[2H])=O
Appearance
Solid powder
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nicotinamide-d4 is the deuterium labeled Nicotinamide. Nicotinamide is an inhibitor of SIRT1.
In vitro activity:
To determine the metabolic fate of the NF in blood, an in vitro study was conducted in which equal amounts of 13C‐ and deuterium‐labelled nicotinamide riboside chloride were added to water, heparinised whole blood, heparinised plasma, and serum at a concentration of 39 μM. The nicotinamide riboside and NAM contents of the samples were analysed immediately (T0) or after incubation at 37°C for 5 and 10 min. Compared to T0, there was no significant change in the amount of nicotinamide riboside or NAM in water, plasma, and serum samples over the course of the 10 min incubation period. In contrast, the amount of nicotinamide riboside in whole blood decreased within 5 min, while the amount of NAM increased. Similar results were obtained when the samples were incubated at 4°C, although the kinetics of the decrease in the amount of nicotinamide riboside and increase in the amount of NAM in whole blood were delayed compared to those observed at 37°C. Similar results have been reported by Liu et al. The Panel notes that these results indicate that the NF can be metabolised to NAM in a cellular component of whole blood. Reference: EFSA J. 2019 Aug; 17(8): e05775. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7009190/
In vivo activity:
Exposure to degeneration-inducing levels of light suppressed retinal NAD+ levels. Mice undergoing light-induced retinal degeneration exhibited significantly suppressed retinal function, severely disrupted photoreceptor cell layers, and increased apoptosis and inflammation in the outer retina. Treatment with NR increased levels of NAD+ in retina and prevented these deleterious outcomes. This study is the first to report the protective effects of NR treatment in a mouse model of retinal degeneration. The positive outcomes, coupled with human tolerance to NR dosing, suggest that maintaining retinal NAD+ via systemic NR treatment should be further explored for clinical relevance. Reference: Invest Ophthalmol Vis Sci. 2020 Aug; 61(10): 47. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7452859/
Solvent mg/mL mM
Solubility
DMF 15.0 118.90
DMSO 15.0 118.90
Ethanol 2.5 19.82
PBS (pH 7.2) 10.0 79.27
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 126.15 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. EFSA Panel on Nutrition, Novel foods and Food allergens (NDA), Turck D, Castenmiller J, de Henauw S, Hirsch-Ernst KI, Kearney J, Maciuk A, Mangelsdorf I, McArdle HJ, Naska A, Pelaez C, Pentieva K, Siani A, Thies F, Tsabouri S, Vinceti M, Cubadda F, Engel KH, Frenzel T, Heinonen M, Marchelli R, Neuhäuser-Berthold M, Pöting A, Poulsen M, Sanz Y, Schlatter JR, van Loveren Agnès de Sesmaisons-Lecarré H, Germini A, Knutsen HK. Safety of nicotinamide riboside chloride as a novel food pursuant to Regulation (EU) 2015/2283 and bioavailability of nicotinamide from this source, in the context of Directive 2002/46/EC. EFSA J. 2019 Aug 7;17(8):e05775. doi: 10.2903/j.efsa.2019.5775. PMID: 32626405; PMCID: PMC7009190. 2. Conze D, Brenner C, Kruger CL. Safety and Metabolism of Long-term Administration of NIAGEN (Nicotinamide Riboside Chloride) in a Randomized, Double-Blind, Placebo-controlled Clinical Trial of Healthy Overweight Adults. Sci Rep. 2019 Jul 5;9(1):9772. doi: 10.1038/s41598-019-46120-z. PMID: 31278280; PMCID: PMC6611812. 3. Zhang X, Henneman NF, Girardot PE, Sellers JT, Chrenek MA, Li Y, Wang J, Brenner C, Nickerson JM, Boatright JH. Systemic Treatment With Nicotinamide Riboside Is Protective in a Mouse Model of Light-Induced Retinal Degeneration. Invest Ophthalmol Vis Sci. 2020 Aug 3;61(10):47. doi: 10.1167/iovs.61.10.47. PMID: 32852543; PMCID: PMC7452859.
In vitro protocol:
1. EFSA Panel on Nutrition, Novel foods and Food allergens (NDA), Turck D, Castenmiller J, de Henauw S, Hirsch-Ernst KI, Kearney J, Maciuk A, Mangelsdorf I, McArdle HJ, Naska A, Pelaez C, Pentieva K, Siani A, Thies F, Tsabouri S, Vinceti M, Cubadda F, Engel KH, Frenzel T, Heinonen M, Marchelli R, Neuhäuser-Berthold M, Pöting A, Poulsen M, Sanz Y, Schlatter JR, van Loveren Agnès de Sesmaisons-Lecarré H, Germini A, Knutsen HK. Safety of nicotinamide riboside chloride as a novel food pursuant to Regulation (EU) 2015/2283 and bioavailability of nicotinamide from this source, in the context of Directive 2002/46/EC. EFSA J. 2019 Aug 7;17(8):e05775. doi: 10.2903/j.efsa.2019.5775. PMID: 32626405; PMCID: PMC7009190.
In vivo protocol:
1. Conze D, Brenner C, Kruger CL. Safety and Metabolism of Long-term Administration of NIAGEN (Nicotinamide Riboside Chloride) in a Randomized, Double-Blind, Placebo-controlled Clinical Trial of Healthy Overweight Adults. Sci Rep. 2019 Jul 5;9(1):9772. doi: 10.1038/s41598-019-46120-z. PMID: 31278280; PMCID: PMC6611812. 2. Zhang X, Henneman NF, Girardot PE, Sellers JT, Chrenek MA, Li Y, Wang J, Brenner C, Nickerson JM, Boatright JH. Systemic Treatment With Nicotinamide Riboside Is Protective in a Mouse Model of Light-Induced Retinal Degeneration. Invest Ophthalmol Vis Sci. 2020 Aug 3;61(10):47. doi: 10.1167/iovs.61.10.47. PMID: 32852543; PMCID: PMC7452859.
1: Novak Kujundžić R, Prpić M, Đaković N, Dabelić N, Tomljanović M, Mojzeš A, Fröbe A, Trošelj KG. Nicotinamide N-Methyltransferase in Acquisition of Stem Cell Properties and Therapy Resistance in Cancer. Int J Mol Sci. 2021 May 26;22(11):5681. doi: 10.3390/ijms22115681. PMID: 34073600; PMCID: PMC8197977. 2: Gao Y, Martin NI, van Haren MJ. Nicotinamide N-methyl transferase (NNMT): An emerging therapeutic target. Drug Discov Today. 2021 May 21:S1359-6446(21)00242-7. doi: 10.1016/j.drudis.2021.05.011. Epub ahead of print. PMID: 34029690. 3: Khaidizar FD, Bessho Y, Nakahata Y. Nicotinamide Phosphoribosyltransferase as a Key Molecule of the Aging/Senescence Process. Int J Mol Sci. 2021 Apr 2;22(7):3709. doi: 10.3390/ijms22073709. PMID: 33918226; PMCID: PMC8037941. 4: Hosseini L, Mahmoudi J, Pashazadeh F, Salehi-Pourmehr H, Sadigh-Eteghad S. Protective Effects of Nicotinamide Adenine Dinucleotide and Related Precursors in Alzheimer's Disease: A Systematic Review of Preclinical Studies. J Mol Neurosci. 2021 Apr 28. doi: 10.1007/s12031-021-01842-6. Epub ahead of print. PMID: 33907963. 5: Navarro MN, Gómez de Las Heras MM, Mittelbrunn M. Nicotinamide adenine dinucleotide metabolism in the immune response, autoimmunity and inflammageing. Br J Pharmacol. 2021 Apr 5. doi: 10.1111/bph.15477. Epub ahead of print. PMID: 33817782. 6: Suchard MS, Savulescu DM. Nicotinamide pathways as the root cause of sepsis - an evolutionary perspective on macrophage energetic shifts. FEBS J. 2021 Mar 8. doi: 10.1111/febs.15807. Epub ahead of print. PMID: 33686748. 7: Giacalone S, Spigariolo CB, Bortoluzzi P, Nazzaro G. Oral nicotinamide: The role in skin cancer chemoprevention. Dermatol Ther. 2021 May;34(3):e14892. doi: 10.1111/dth.14892. Epub 2021 Mar 1. PMID: 33595161. 8: Fragoso-Morales LG, Correa-Basurto J, Rosales-Hernández MC. Implication of Nicotinamide Adenine Dinucleotide Phosphate (NADPH) Oxidase and Its Inhibitors in Alzheimer's Disease Murine Models. Antioxidants (Basel). 2021 Feb 2;10(2):218. doi: 10.3390/antiox10020218. PMID: 33540840; PMCID: PMC7912941. 9: Roberti A, Fernández AF, Fraga MF. Nicotinamide N-methyltransferase: At the crossroads between cellular metabolism and epigenetic regulation. Mol Metab. 2021 Mar;45:101165. doi: 10.1016/j.molmet.2021.101165. Epub 2021 Jan 14. PMID: 33453420; PMCID: PMC7868988. 10: Hussain S, Singh A, Alshammari TM, Habib A, Hussain MS, Jha R, Akhtar M, Najmi AK. Nicotinamide Therapy in Dialysis Patients: A Systematic Review of Randomized Controlled Trials. Saudi J Kidney Dis Transpl. 2020 Sep- Oct;31(5):883-897. doi: 10.4103/1319-2442.301195. PMID: 33229753. 11: Maiese K. Nicotinamide: Oversight of Metabolic Dysfunction Through SIRT1, mTOR, and Clock Genes. Curr Neurovasc Res. 2020;17(5):765-783. doi: 10.2174/1567202617999201111195232. PMID: 33183203; PMCID: PMC7914159. 12: Immanuel S, Sivasubramanian R, Gul R, Dar MA. Recent Progress and Perspectives on Electrochemical Regeneration of Reduced Nicotinamide Adenine Dinucleotide (NADH). Chem Asian J. 2020 Dec 14;15(24):4256-4270. doi: 10.1002/asia.202001035. Epub 2020 Nov 19. PMID: 33164351. 13: Badawy AA. Immunotherapy of COVID-19 with poly (ADP-ribose) polymerase inhibitors: starting with nicotinamide. Biosci Rep. 2020 Oct 30;40(10):BSR20202856. doi: 10.1042/BSR20202856. PMID: 33063092; PMCID: PMC7601349. 14: Elamin M, Ruskin DN, Sacchetti P, Masino SA. A unifying mechanism of ketogenic diet action: The multiple roles of nicotinamide adenine dinucleotide. Epilepsy Res. 2020 Nov;167:106469. doi: 10.1016/j.eplepsyres.2020.106469. Epub 2020 Sep 14. PMID: 33038721. 15: King E, Maxel S, Li H. Engineering natural and noncanonical nicotinamide cofactor-dependent enzymes: design principles and technology development. Curr Opin Biotechnol. 2020 Dec;66:217-226. doi: 10.1016/j.copbio.2020.08.005. Epub 2020 Sep 18. PMID: 32956903; PMCID: PMC7744333. 16: Aghelan Z, Kiani S, Nasiri A, Sadeghi M, Farrokhi A, Khodarahmi R. Factors Influencing Mitochondrial Function as a Key Mediator of Glucose-Induced Insulin Release: Highlighting Nicotinamide Nucleotide Transhydrogenase. Int J Mol Cell Med. 2020 Spring;9(2):107-122. doi: 10.22088/IJMCM.BUMS.9.2.107. Epub 2020 Aug 10. PMID: 32934948; PMCID: PMC7489113. 17: Salech F, Ponce DP, Paula-Lima AC, SanMartin CD, Behrens MI. Nicotinamide, a Poly [ADP-Ribose] Polymerase 1 (PARP-1) Inhibitor, as an Adjunctive Therapy for the Treatment of Alzheimer's Disease. Front Aging Neurosci. 2020 Aug 13;12:255. doi: 10.3389/fnagi.2020.00255. PMID: 32903806; PMCID: PMC7438969. 18: Tannous C, Booz GW, Altara R, Muhieddine DH, Mericskay M, Refaat MM, Zouein FA. Nicotinamide adenine dinucleotide: Biosynthesis, consumption and therapeutic role in cardiac diseases. Acta Physiol (Oxf). 2021 Mar;231(3):e13551. doi: 10.1111/apha.13551. Epub 2020 Sep 21. PMID: 32853469. 19: Griffiths HBS, Williams C, King SJ, Allison SJ. Nicotinamide adenine dinucleotide (NAD+): essential redox metabolite, co-substrate and an anti-cancer and anti-ageing therapeutic target. Biochem Soc Trans. 2020 Jun 30;48(3):733-744. doi: 10.1042/BST20190033. PMID: 32573651. 20: Ramsden DB, Waring RH, Parsons RB, Barlow DJ, Williams AC. Nicotinamide N-Methyltransferase: Genomic Connection to Disease. Int J Tryptophan Res. 2020 Jun 4;13:1178646920919770. doi: 10.1177/1178646920919770. PMID: 32547055; PMCID: PMC7273554.

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