3-CARBAMYL-1-METHYLPYRIDINIUM CHLORIDE Chemical Properties

Melting point:

207-209℃ (water acetone )

storage temp. 

room temp

solubility 

H2O: soluble15mg/mL, clear

form 

crystalline

color 

white

Water Solubility 

almost transparency

Merck 

14,9693

CAS DataBase Reference

1005-24-9(CAS DataBase Reference)

Safety Information

WGK Germany 

3

RTECS 

UU1925000

HS Code 

2933.39.9200

MSDS

• Language:English Provider:SigmaAldrich

3-CARBAMYL-1-METHYLPYRIDINIUM CHLORIDE Usage And Synthesis

Description

Nicotinamide is a precursor of NAD and NADP , which serve essential functions in modulating cellular redox status and controlling signaling and transcriptional events. 1-Methylnicotinamide (MNA) is a primary metabolite of nicotinamide produced by the action of nicotinamide N-methyltransferase (NNMT; ). It demonstrates antithrombotic and anti-inflammatory properties through direct action on the endothelium by a mechanism involving the prostacyclin pathway and by improving nitric oxide bioavailability. Aggressive cancer cell lines are reported to have higher levels of MNA due to increased NNMT-directed transfer of methyl groups from S-adenosyl-L-methionine to nicotinamide, implicating a role for MNA in cancer cell metabolism.

Uses

1-Methylnicotinamide chloride may be used as a standard in the quantification of 1-methylnicotinamide in urine samples using ion pairing reverse-phase high performance liquid chromatography (RP-HPLC).

Uses

Nicotinamide is a precursor of NAD and NADP , which serve essential functions in modulating cellular redox status and controlling signaling and transcriptional events. 1-Methylnicotinamide (MNA) is a primary metabolite of nicotinamide produced by the action of nicotinamide N-methyltransferase (NNMT; ). It demonstrates antithrombotic and anti-inflammatory properties through direct action on the endothelium by a mechanism involving the prostacyclin pathway and by improving nitric oxide bioavailability. Aggressive cancer cell lines are reported to have higher levels of MNA due to increased NNMT-directed transfer of methyl groups from S-adenosyl-L-methionine to nicotinamide, implicating a role for MNA in cancer cell metabolism.

General Description

1-Methylnicotinamide (MNA) is a primary metabolite of nicotinamide produced mainly by nicotinamide N-methyltransferase (NNMT) and exhibits antithrombotic and anti-inflammatory effects.

Biochem/physiol Actions

1-Methylnicotinamide (MNA) is a primary metabolite of nicotinamide produced mainly by nicotinamide N-methyltransferase (NNMT). 1-Methylnicotinamide (MNA) has been shown to have antithrombotic and anti-inflammatory effects. A recent study indicated that MNA may exert antithrombotic and anti-inflammatory effects through direct action on the endothelium, with a vasorelaxing effect by enhancement of NO bioavailability and reduction of eNOS-dependent oxidative stress. Enhanced NNMT activity is a feature of many types of cancer. How much direct involvement MNA has in the tumorigenesis associated with overexpression of NNMT is under investigation. MNA by itself increased mitochondrial Complex I activity and increased cancer cell viability in SH-SY5Y neuroblastoma cells that do not produce NNMT.

Purification Methods

Recrystallise it from MeOH. [Beilstein 22 III/IV 468, 22/2 V 80.]

References

[1] THEODORE A. ALSTON  Robert H A. Substrate specificity of nicotinamide methyltransferase isolated from porcine liver[J]. Archives of biochemistry and biophysics, 1988, 260 2: Pages 601-608. DOI: 10.1016/0003-9861(88)90487-0
[2] TERESA B DOMAGALA. Nitric oxide production and endothelium-dependent vasorelaxation ameliorated by N1-methylnicotinamide in human blood vessels.[J]. Hypertension, 2012, 59 4: 825-832. DOI: 10.1161/hypertensionaha.111.183210
[3] S CHLOPICKI. 1-Methylnicotinamide (MNA), a primary metabolite of nicotinamide, exerts anti-thrombotic activity mediated by a cyclooxygenase-2/prostacyclin pathway[J]. British Journal of Pharmacology, 2009, 152 2: 230-239. DOI: 10.1038/sj.bjp.0707383

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