Nicotinamide mononucleotide
Chemical compound
From Wikipedia, the free encyclopedia
Nicotinamide mononucleotide ("NMN" and "β-NMN") is a nucleotide derived from ribose, nicotinamide, nicotinamide riboside and niacin.[citation needed] In humans, several enzymes use NMN to generate nicotinamide adenine dinucleotide (NADH).[citation needed][1] In mice, it has been proposed that NMN is absorbed via the small intestine within 10 minutes of oral uptake and converted to nicotinamide adenine dinucleotide (NAD+ form)[2] through the Slc12a8 transporter.[3] However, this observation has been challenged,[4] and the matter remains unsettled.[5]
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| Names | |
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| IUPAC name
3-Carbamoyl-1-(5-O-phosphono-β-D-ribofuranosyl)pyridin-1-ium | |
| Systematic IUPAC name
[(2R,3S,4R,5R)-5-(3-Carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| 3570187 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.012.851 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C11H15N2O8P | |
| Molar mass | 334.221 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Because NADH is a cofactor for processes inside mitochondria, for sirtuins and PARP, NMN has been studied in animal models as a potential neuroprotective and anti-aging agent.[6][7] The alleged anti-aging effect at the cellular level by inhibiting mitochondrial decay in presence of increased levels of NAD+ makes it popular among anti-aging products.[8] Dietary supplement companies have aggressively marketed NMN products, claiming those benefits.[9][10] However, no human studies to date have properly proven its anti-aging effects with proposed health benefits only suggested through research done in vitro or through animal models.[11] Single-dose administration of up to 500 mg was shown safe in men in a study at Keio University.[12] One 2021 clinical trial found that NMN improved muscular insulin sensitivity in prediabetic women,[13] while another found that it improved aerobic capacity in amateur runners.[14] A 2023 clinical trial showed that NMN improves performance on a six-minute walking test and a subjective general health assessment.[15]
NMN is vulnerable to extracellular degradation by CD38 enzyme,[16] which can be inhibited by compounds such as CD38-IN-78c.[17]
Dietary sources
Production
Different expressions of NMN across human organs
The synthesizing enzymes and consumption enzymes of NMN also exhibit tissue specificity: NMN is widely distributed in tissues and organs throughout the body and has been present in various cells since embryonic development.[22]
Potential benefits and risks
NMN is a precursor for NAD+ biosynthesis, and NMN dietary supplementation has been demonstrated to increase NAD+ concentration and thus has the potential to mitigate aging-related disorders such as oxidative stress, DNA damage, neurodegeneration and inflammatory responses.[26] The potential benefits and risks of NMN supplementation, as of 2023, are under investigation.[26]
Certain enzymes are sensitive to the intracellular NMN/NAD+ ratio, such as SARM1,[27] a protein responsible for initiating cellular degeneration pathways such as MAP kinase and inducing axonal loss and neuronal death.[28][29] NMNAT is an enzyme with neurorescuing properties that functions to deplete NMN and produce NAD+, attenuating SARM1 activity and aiding neuronal survival in vitro,[30][31] an effect that is reversed by applying exogenous NMN which promptly resumed axon destruction.[28] The similar molecule nicotinic acid mononucleotide (NaMN) opposes the activating effect of NMN on SARM1, and is a neuroprotector.[32]