Names | |
---|---|
Preferred IUPAC name
3-Carbamoyl-1-methylpyridin-1-ium | |
Other names
Trigonellamide; N1-Methylnicotinamide; NMN
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
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).
|
1-Methylnicotinamide (trigonellamide) is a prototypic organic cation. [1] 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.
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]
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]
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[ check spelling] 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]
Names | |
---|---|
Preferred IUPAC name
3-Carbamoyl-1-methylpyridin-1-ium | |
Other names
Trigonellamide; N1-Methylnicotinamide; NMN
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
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).
|
1-Methylnicotinamide (trigonellamide) is a prototypic organic cation. [1] 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.
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]
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]
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[ check spelling] 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]