View source for Nicotinamide mononucleotide/en

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{{Chembox
<!-- Images -->
| ImageFile = Nicotinamide mononucleotide.svg
| ImageSize = 220px
<!-- Names -->
| IUPACName = 3-Carbamoyl-1-(5-''O''-phosphono-β-<small>D</small>-ribofuranosyl)pyridin-1-ium
| SystematicName = [(2''R'',3''S'',4''R'',5''R'')-5-(3-Carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
| OtherNames = {{unbulleted list | Nicotinamide ribonucleoside 5′-phosphate | Nicotinamide <small>D</small>-ribonucleotide | β-Nicotinamide ribose monophosphate| Nicotinamide nucleotide }}
<!-- Sections -->
| Section1 = {{Chembox Identifiers
| CASNo =  1094-61-7 
| CASNo_Ref = {{cascite|correct|CAS}}
| Beilstein = 3570187
| ChEBI = 16171
| ChEMBL = 610238
| EINECS = 214-136-5
| KEGG = C00455
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2KG6QX4W0V
| PubChem = 16219737
| ChemSpiderID = 13553
| SMILES = c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)[O-])O)O)C(=O)N
| StdInChI = 1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/t7-,8-,9-,11-/m1/s1
| StdInChIKey = DAYLJWODMCOQEW-TURQNECASA-N
  }}
| Section2 = {{Chembox Properties
| C=11|H=15|N=2|O=8|P=1
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| Section3 = {{Chembox Hazards
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'''Nicotinamide mononucleotide''' ("'''NMN'''" and "'''β-NMN'''") is a [[nucleotide]] derived from [[ribose]], [[nicotinamide]], [[nicotinamide riboside]] and [[Niacin (substance)|niacin]]. In humans, several enzymes use NMN to generate [[nicotinamide adenine dinucleotide]] (NADH). 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 ([[Nicotinamide adenine dinucleotide|NAD+]]) through the [[SLC12A8|Slc12a8]] transporter. and the matter remains unsettled.

Because NADH is a [[Cofactor (biochemistry)|cofactor]] for processes inside [[mitochondria]], for [[sirtuin]]s and [[Poly (ADP-ribose) polymerase|PARP]], NMN has been studied in [[animal model]]s as a potential neuroprotective and [[anti-aging]] agent. The reversal of aging at the cellular level by inhibiting [[mitochondrial decay]] in presence of increased levels of NAD+ makes it popular among anti-aging products. Dietary supplement companies have [[Hard sell|aggressively marketed]] NMN products, claiming those benefits. 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 testing|animal models]]. Single-dose administration of up to 500 mg was shown safe in men in a study at [[Keio University]]. One 2021 clinical trial found that NMN improved muscular insulin sensitivity in prediabetic women, while another found that it improved aerobic capacity in amateur runners. A 2023 clinical trial showed that NMN improves performance on a six-minute walking test and a subjective general health assessment.

NMN is vulnerable to extracellular degradation by [[CD38]] enzyme, which can be inhibited by compounds such as [[CD38-IN-78c]].

== Dietary sources ==
NMN is found in fruits and vegetables such as [[edamame]], [[broccoli]], [[cabbage]], [[cucumber]] and [[avocado]] at a concentration of about 1 mg per 100g, making these natural sources impractical to acquire the quantities needed to accomplish the dosing currently being investigated for NMN as a pharmaceutical.

== Production ==
Production of nicotinamide mononucleotide has been redacted since the latter half of 2022 by the [[Food and Drug Administration|FDA]] because it is under investigation as a pharmaceutical drug.

== 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.

==Potential benefits and risks==

NMN is a precursor for [[Nicotinamide adenine dinucleotide|NAD<sup>+</sup>]] biosynthesis, and NMN dietary supplementation has been demonstrated to increase NAD<sup>+</sup> concentration and thus has the potential to mitigate aging-related disorders such as [[oxidative stress]], [[DNA damage (naturally occurring)|DNA damage]], [[Neurodegenerative disease|neurodegeneration]] and [[inflammation|inflammatory responses]]. Song Q, Zhou X, Xu K, Liu S, Zhu X, Yang J. The Safety and Antiaging Effects of Nicotinamide Mononucleotide in Human Clinical Trials: an Update. Adv Nutr. 2023 Nov;14(6):1416-1435. doi: 10.1016/j.advnut.2023.08.008. Epub 2023 Aug 22. PMID: 37619764; PMCID: PMC10721522</ref> The potential benefits and risks of NMN supplementation, as of 2023, are currently under investigation.

Certain enzymes are sensitive to the intracellular NMN/[[Nicotinamide adenine dinucleotide|NAD<sup>+</sup>]] ratio, such as [[SARM1]], a protein responsible for initiating cellular degeneration pathways such as [[MAP kinase]] and inducing [[axon|axonal]] loss and [[necrosis|neuronal death]]. [[NMNAT1|NMNAT]] is an enzyme with neurorescuing properties that functions to deplete NMN and produce NAD<sup>+</sup>, attenuating SARM1 activity and aiding neuronal survival ''in-vitro'', an effect that is reversed by applying exogenous NMN which promptly resumed axon destruction. The similar molecule nicotinic acid mononucleotide (NaMN) opposes the activating effect of NMN on [[SARM1]], and is a neuroprotector.

{{二次利用|date=5 April 2024}}
[[Category:Nucleotides]]
[[Category:Ribosides]]
[[Category:Nicotinamides]]
[[Category:Anti-aging substances]]