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| Names | |
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Preferred IUPAC name
3-Carbamoyl-1-methylpyridin-1-ium | |
| Other names
Trigonellamide; N1-Methylnicotinamide; NMN
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
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PubChem CID
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| UNII | |
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CompTox Dashboard (EPA)
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| Properties | |
| C7H9N2O+ | |
| Molar mass | 137.161 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Methylnicotinamide (trigonellamide) is a prototypic organic cation. 1-Methylnicotinamide is the methylated amide of Nicotinamide (niacinamide, vitamin B3).
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. 1-Methylnicotinamide is also present in the Judas' ear fungus and in green tea.
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. 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.NNMT is highly expressed in the human liver.
Use
For a long time, 1-methylnicotinamide was considered a biologically inactive metabolite of nicotinamide. However, various studies show antithrombotic, anti-inflammatory, gastroprotective and vasoprotective properties.
1-Methylnicotinamide is an endogenous activator of prostacyclin synthesis and can therefore regulate thrombolytic and inflammatory processes in the cardiovascular system. It inhibits platelet-dependent thrombosis through a mechanism involvingcyclooxygenase-2 and prostacyclin and increases nitric oxide bioavailability in the endothelium.
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.
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.
1-Methylnicotinamide is used in cosmetic products such as hair- and skincare products and as a dietary supplement.