Nicotinamide mononucleotide

Nicotinamide mononucleotide
Names
	IUPAC name 3-Carbamoyl-1-[5-O-(hydroxyphosphinato)-β-D-ribofuranosyl]pyridinium
	Other names Nicotinamide ribonucleoside 5'-phosphate; Nicotinamide D-ribonucleotide; β-Nicotinamide ribose monophosphate; Nicotinamide nucleotide;
Identifiers
CAS Number	1094-61-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	13553;
ECHA InfoCard	100.012.851
PubChem CID	16219737;
UNII	2KG6QX4W0V ;
CompTox Dashboard (EPA)	DTXSID50911152 ;
	InChI InChI=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 Key: DAYLJWODMCOQEW-TURQNECASA-N;
	SMILES c1cc(c[n+](c1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)[O-])O)O)C(=O)N;
Properties
Chemical formula	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).
	Infobox references

Nicotinamide mononucleotide ("NMN", "NAMN", and "β-NMN") is a nucleotide derived from ribose and nicotinamide.[1] Like nicotinamide riboside, NMN is a derivative of niacin[2], and humans have enzymes that can use NMN to generate nicotinamide adenine dinucleotide (NADH).[1] In mice, NMN enters cells via the small intestines within 10 minutes converting to NAD+ through the Slc12a8 NMN transporter.[3] Because NADH is a cofactor for processes inside mitochondria, for sirtuins, and for PARP, NMN has been studied in animal models as a potential neuroprotective and anti-aging agent.[4][5] Dietary supplement companies have aggressively marketed NMN products claiming those benefits.[6] Doses of up to 500 mg was shown safe in men in a recent human study[7] at Keio University School of Medicine, Shinjuku, Tokyo Japan. Multiple long-term human studies are underway.[8] [9]

References

Bogan, KL; Brenner, C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annual Review of Nutrition. 28: 115–30. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.
"About NMN (Beta-Nicotinamide Mononucleotide)".
"Slc12a8 is a nicotinamide mononucleotide transporter". Nature. January 2019.
Brazill, JM; Li, C; Zhu, Y; Zhai, RG (June 2017). "NMNAT: It's an NAD⁺ synthase… It's a chaperone… It's a neuroprotector". Current Opinion in Genetics & Development. 44: 156–162. doi:10.1016/j.gde.2017.03.014. PMC 5515290. PMID 28445802.
"Long-Term Administration of Nicotinamide Mononucleotide Mitigates Age-Associated Physiological Decline in Mice". Cell Metabolism. 13 December 2016.
Stipp, David (March 11, 2015). "Beyond Resveratrol: The Anti-Aging NAD Fad". Scientific American Blog Network.
"Effect of oral administration of nicotinamide mononucleotide on clinical parameters and nicotinamide metabolite levels in healthy Japanese men". Endocrine Journal. November 2019.
"Effect of long-term oral administration of nicotinamide mononucleotide (NMN) on human health".
"Assessment of the safety of long-term nicotinamide mononucleotide (NMN)".

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[Bogan2008-1] Bogan, KL; Brenner, C (2008). "Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition". Annual Review of Nutrition. 28: 115–30. doi:10.1146/annurev.nutr.28.061807.155443. PMID 18429699.

[2] "About NMN (Beta-Nicotinamide Mononucleotide)".

[3] "Slc12a8 is a nicotinamide mononucleotide transporter". Nature. January 2019.

[4] Brazill, JM; Li, C; Zhu, Y; Zhai, RG (June 2017). "NMNAT: It's an NAD⁺ synthase… It's a chaperone… It's a neuroprotector". Current Opinion in Genetics & Development. 44: 156–162. doi:10.1016/j.gde.2017.03.014. PMC 5515290. PMID 28445802.

[5] "Long-Term Administration of Nicotinamide Mononucleotide Mitigates Age-Associated Physiological Decline in Mice". Cell Metabolism. 13 December 2016.

[6] Stipp, David (March 11, 2015). "Beyond Resveratrol: The Anti-Aging NAD Fad". Scientific American Blog Network.

[7] "Effect of oral administration of nicotinamide mononucleotide on clinical parameters and nicotinamide metabolite levels in healthy Japanese men". Endocrine Journal. November 2019.

[8] "Effect of long-term oral administration of nicotinamide mononucleotide (NMN) on human health".

[9] "Assessment of the safety of long-term nicotinamide mononucleotide (NMN)".