1-Methylnicotinamide

1-Methylnicotinamide (trigonellamide) is a prototypic organic cation.[1] 1-Methylnicotinamide is the methylated amide of Nicotinamide (niacinamide, vitamin B3).

1-Methylnicotinamide
Names
Preferred IUPAC name
3-Carbamoyl-1-methylpyridin-1-ium
Other names
Trigonellamide; N1-Methylnicotinamide; NMN
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
SMILES
  • C[N+]1=CC=CC(=C1)C(=O)N
Properties
Chemical formula
 C7H9N2O+
Molar mass 137.161 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

1-Methylnicotinamide is an endogenic substance that is produced in the liver when Nicotinamide is metabolized. It is a typical substance secreted in the kidney.

Occurrence

The highest natural concentration of 1-methylnicotinamide found so far is in the alga Undaria pinnatifida.[2] 1-Methylnicotinamide is also present in the Judas' ear fungus and in green tea.[2]

Extraction and production

1-Methylnicotinamide can be produced in the liver by nicotinamide N-methyltransferase. The reaction takes place during the metabolism of NAD (nicotinamide adenine dinucleotide).

NNMT (nicotinamide N-methyltransferase) is an enzyme that in humans is encoded by the NNMT gene.[3] NNMT catalyzes the methylation of nicotinamide and similar compounds using the methyl donor S-adenosyl methionine (SAM-e) to produce S-adenosyl-L-homocysteine (SAH) and 1-methylnicotinamide.[4] NNMT is highly expressed in the human liver.[4]

Use

For a long time, 1-methylnicotinamide was considered a biologically inactive metabolite of nicotinamide. However, various studies show antithrombotic,[5] anti-inflammatory,[6] gastroprotective[7] and vasoprotective[7] properties.

1-Methylnicotinamide is an endogenous activator of prostacyclin synthesis and can therefore regulate thrombolytic and inflammatory processes in the cardiovascular system.[8] It inhibits platelet-dependent thrombosis through a mechanism involving[9] cyclooxygenase-2 and prostacyclin and increases nitric oxide bioavailability in the endothelium.[7][4]

Animal experiments with diabetic rats have shown that 1-methylnicotinamide has a positive effect on degenerative changes in the brain and cognitive performance can be thus longer maintained.[10]

Experiments with the nematode Caenorhabditis elegans showed that the addition of 1-methylnicotinamide can extend their lifespan. This may possibly be attributed to increased free radical binding and the resulting reduced oxidative stress.[11]

1-Methylnicotinamide is used in cosmetic products such as hair- and skincare products and as a dietary supplement.[12]

References
  1. Sokol, P. P.; Holohan, P. D.; Ross, C. R. (1986). "Essential disulfide and sulfhydryl groups for organic cation transport in renal brush-border membranes". Journal of Biological Chemistry. 261 (7): 3282–3287. doi:10.1016/S0021-9258(17)35779-4. PMID 2936734. Retrieved 5 March 2021.
  2. Taguchi, H.; Sakaguchi, M.; Shimabayashi, Y. (1986). 各種食品中のキノリン酸,トリゴネリンおよびN1-メチルニコチンアミドの含量ならびに加熱によるそれらのニコチン酸,ニコチンアミドへの変換 [Contents of quinolinic acid, trigonelline and N1-methylnicotinamide in various foods and thermal conversion of these compounds into nicotinic acid and nicotinamide]. ビタミン ビタミン [Vitamins] (in Japanese). 60 (11): 537–546. doi:10.20632/vso.60.11_537.
  3. Aksoy S, Brandriff BF, Ward A, Little PF, Weinshilboum RM (Mar 1996). "Human nicotinamide N-methyltransferase gene: molecular cloning, structural characterization and chromosomal localization". Genomics. 29 (3): 555–561. doi:10.1006/geno.1995.9966. PMID 8575745.
  4. Pissios P (2017). "Nicotinamide N-Methyltransferase: More Than a Vitamin B3 Clearance Enzyme". Trends in Endocrinology and Metabolism. 28 (5): 340–353. doi:10.1016/j.tem.2017.02.004. PMC 5446048. PMID 28291578.
  5. Gębicki, J.; Sysa-Jędrzejowska, A.; Adamus, J.; Woźniacka, A.; Rybak, M.; Zielonka, J. (2003). "1-Methylnicotinamide: A potent anti-inflammatory agent of vitamin origin" (PDF). Polish Journal of Pharmacology. 55 (1): 109–112. PMID 12856834.
  6. Bryniarski, K.; Biedron, R.; Jakubowski, A.; Chlopicki, S.; Marcinkiewicz, J. (2008). "Anti-inflammatory effect of 1-methylnicotinamide in contact hypersensitivity to oxazolone in mice; involvement of prostacyclin". European Journal of Pharmacology. 578 (2–3): 332–338. doi:10.1016/j.ejphar.2007.09.011. PMID 17935712.
  7. Domagala, T. B.; Szeffler, A.; Dobrucki, L. W.; Dropinski, J.; Polanski, S.; Leszczynska-Wiloch, M.; Kotula-Horowitz, K.; Wojciechowski, J.; Wojnowski, L.; Szczeklik, A.; Kalinowski, L. (2012). "Nitric oxide production and endothelium-dependent vasorelaxation ameliorated by N1-methylnicotinamide in human blood vessels". Hypertension. 59 (4): 825–832. doi:10.1161/HYPERTENSIONAHA.111.183210. PMID 22353616. S2CID 302943.
  8. Bartuś, M.; Łomnicka, M.; Kostogrys, R. B.; Kaźmierczak, P.; Watała, C.; Słominska, E. M.; Smoleński, R. T.; Pisulewski, P. M.; Adamus, J.; Gębicki, J.; Chlopicki, S. (2008). "1-Methylnicotinamide (MNA) prevents endothelial dysfunction in hypertriglyceridemic and diabetic rats" (PDF). Pharmacological Reports. 60 (1): 127–138. PMID 18276994.
  9. Chlopicki, S.; Swies, J.; Mogielnicki, A.; Buczko, W.; Bartus, M.; Lomnicka, M.; Adamus, J.; Gebicki, J. (2007). "1-Methylnicotinamide (MNA), a primary metabolite of nicotinamide, exerts anti-thrombotic activity mediated by a cyclooxygenase-2/prostacyclin pathway". British Journal of Pharmacology. 152 (2): 230–239. doi:10.1038/sj.bjp.0707383. PMC 1978255. PMID 17641676.
  10. Kuchmerovska, T.; Shymanskyy, I.; Chlopicki, S.; Klimenko, A. (2010). "1-Methylnicotinamide (MNA) in prevention of diabetes-associated brain disorders". Neurochemistry International. 56 (2): 221–228. doi:10.1016/j.neuint.2009.10.004. PMID 19837120. S2CID 21785102.
  11. Schmeisser, K.; Mansfeld, J.; Kuhlow, D.; Weimer, S.; et al. (2013). "Role of sirtuins in lifespan regulation is linked to methylation of nicotinamide". Nature Chemical Biology. 9 (11): 693–700. doi:10.1038/nchembio.1352. PMC 4076143. PMID 24077178.
  12. "Menavitin Produkte, die das Molekül 1-MNA beinhalten: das Novel Food mit natürlicher Intelligenz". Startup Valley (in German). 21 November 2019. Retrieved 29 January 2020.


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