1-methyl nicotinamide

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of 1-methylnicotinamide
General
Surname 1-methyl nicotinamide
other names
  • 1-methylpyridin-1-ium-3-carboxamide ( IUPAC )
  • Trigonellinamide
  • N1-methyl nicotinamide
  • Tria-662
Molecular formula
  • C 7 H 9 N 2 O +
  • C 7 H 9 N 2 OCl (chloride)
Brief description

White dust

External identifiers / databases
CAS number
  • 3106-60-3
  • 1005-24-9 (chloride)
  • 6456-44-6 (iodide)
PubChem 457
ChemSpider 444
DrugBank DB11710
Wikidata Q16891873
properties
Molar mass
  • 137.16 g mol −1
  • 172.61 g mol −1 (chloride)
Physical state

firmly

Melting point

207-209 ° C (chloride)

solubility

easily in water (15 mg ml −1 at 20 ° C) (chloride)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

2400 mg kg −1 ( LD 50 ,  rat , subcutaneous )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-methylnicotinamide is the methylated amide of nicotinic acid (niacin, vitamin B 3 ). It is a substance produced by the body when nicotinic acid is metabolized in the liver.

Occurrence

The highest natural concentration of 1-methylnicotinamide can be found in the alga Undaria pinnatifida . It is also found in the Judas ear mushroom and green tea .

Extraction and presentation

1-methylnicotinamide is primarily produced in the liver by the nicotinamide N-methyltransferase. The reaction takes place during the metabolism of NAD ( nicotinamide adenine dinucleotide ). 1-Methylnicotinamide can be produced synthetically with methylation reagents and nicotinamide .

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 trombolytic and inflammatory processes in the cardiovascular system. It inhibits platelet-dependent thrombosis through a mechanism involving cyclooxygenase-2 and prostacyclin and increases nitric oxide bioavailability in the endothelium .

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

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

1-methylnicotinamide is used in cosmetics, such as hair and skin care products, and as a dietary supplement.

Individual evidence

  1. ↑ a b c d e data sheet 1-Methylnicotinamide Chloride from Sigma-Aldrich , accessed on January 29, 2020 ( PDF ).
  2. ↑ External identifiers of or database links to 3-carbamoyl-1-methylpyridinium chloride : CAS number: 1005-24-9, EC number: 463-670-7, ECHA InfoCard: 100.104.777 , PubChem : 70495 , ChemSpider : 63668 , Wikidata : Q27282725 .
  3. ↑ External identifiers or database links to 3-carbamoyl-1-methylpyridinium iodide: CAS number: 6456-44-6, EC number: 229-263-1 , ECHA InfoCard: 100.026.603 , PubChem : 72660 , ChemSpider : 65521 , Wikidata : Q82970083 .
  4. ↑ Kosower, EM; Klinedinst, PE: "Additions of pyridinium rings. II. Charge-transfer complexes as intermediates" in J. Am. Chem. Soc. 78 (1956) 3493-3497.
  5. ↑ a b Taguchi, H .; Sakaguchi, M .; Shimbabayashi, Y .: "Contents of quinolinic acid trigonelline and N-1 methylnicotinamide in various foods and thermal conversion of these compounds into nicotinic acid and nicotinamide" in [Vitamins] 60 (1986) 537-546.
  6. ↑ Gebicki, J .; Sysa-Jedrzejowska, A .; Adamus, J .; Wozniacka, A .; Rybak, M .; Zielonka, J .: "1-methylnicotinamide: a potent anti-inflammatory agent of vitamin origin" in Pol. J. Pharmacol. 55 (2003) 109-112.
  7. ↑ Bryniarski, K .; Biedron, R .; Jakubowski, A .; Chlopicki, S .; Marcinkiewicz, J .: "Anti-inflammatory effect of 1-methylnicotinamide in contact hypersensitivity to oxazolone in mice; involvement of prostacyclin" in Eur. J. Pharmacol. 578 (2008) 332-338.
  8. ↑ a b c Domagala, TB; Szeffler, A .; Dobrucki, LW; Dropinski, J .; Polanski, S .; Leszczynska-Wiloch, M .; Kotula-Horowitz, K .; Wojciechowski, J .; Wojnowski, L .; Szczeklik, A .; Kalinowski, L .: "Nitric oxide production and endothelium-dependent vasorelaxation ameliorated by N1-methylnicotinamide in human blood vessels" in Hypertension 59 (2012) 825-832.
  9. ↑ Bartus, M .; Lomnicka, M .; Kostogrys, RB; Kazmierczak, P .; Watala, C .; Slominska, EM; Smolenski, RT; Pisulewski, PM; Adamus, J .; Gebicki, J .; Chlopicki, S .: "1-Methylnicotinamide (MNA) prevents endothelial dysfunction in hypertriglyceridemic and diabetic rats" in Pharmacol. Rep. 60 (2008) 127-138.
  10. ↑ Chlopicki, S .; Swies, J .; Mogielnicki, A .; Buczko, W .; Bartus, M .; Lomnicka, M .; Adamus, J .; Gebicki, J .: "1-Methylnicotinamide (MNA), a primary metabolite of nicotinamide, exerts anti-thrombotic activity mediated by a cyclooxygenase-2 / prostacyclin pathway" in Br. J. Pharmacol. 152 (2007) 230-239.
  11. ↑ Kuchmerovska, T .; Shymanskyy, I .; Chlopicki, S .; Klimenko, A.: "1-methylnicotinamide (MNA) in prevention of diabetes-associated brain disorders." in Neurochem. Int. 56 (2010) 221-228.
  12. ↑ Schmeisser, K .; Mansfeld, J .; Kuhlow, D .; Weimer, S .; Priebe, S .; Savior, I .; Birringer, M .; Groth, M .; Segref, A .; Kanfi, Y .: "Role of Sirtuins in Lifespan Regulation is Linked to Methylation of Nicotinamide" in Nat. Chem. Biol. 9 (2013) 693-700.
  13. ↑ Entry of 1-methylnicotinamide on startupvalley.de , accessed on January 29, 2020.