1005-24-9

Basic information

• Product Name: 3-CARBAMYL-1-METHYLPYRIDINIUM CHLORIDE
• Synonyms: NICOTINAMIDE CHLOROMETHYLATE;N-METHYLNICOTINIC ACID AMIDE CHLORIDE SALT;N1-METHYLNICOTINAMIDE CHLORIDE;TRIGONELLAMIDE CHLORIDE;1-METHYLPYRIDINE-3-CARBOXYLIC ACID AMIDE CHLORIDE;1-METHYLNICOTINAMIDE CHLORIDE;1-METHYLNICOTINAMIDE CHLORIDE SALT;3-CARBAMOYL-1-METHYLPYRIDINIUM CHLORIDE
• CAS NO: 1005-24-9
• Molecular Formula: C₇H₉N₂O*Cl
• Molecular Weight: 172.61
• EINECS: 463-670-7
• Product Categories: Pyridinium Compounds
• Mol File: 1005-24-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 207-209℃ (water acetone )
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/crystalline
• Density: g/cm³
• Storage Temp.: room temp
• Solubility: H2O: soluble15mg/mL, clear
• Water Solubility: almost transparency
• Merck: 14,9693
• CAS DataBase Reference: 3-CARBAMYL-1-METHYLPYRIDINIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CARBAMYL-1-METHYLPYRIDINIUM CHLORIDE(1005-24-9)
• EPA Substance Registry System: 3-CARBAMYL-1-METHYLPYRIDINIUM CHLORIDE(1005-24-9)

Safety Data

• WGK Germany: 3
• RTECS: UU1925000
• Hazardous Substances Data: 1005-24-9(Hazardous Substances Data)

Usage

Description

3-Carbamylmethylpyridinium chloride is a chemical compound derived from the methylation of 1-methylnicotinamide (MNA), which is a primary metabolite of nicotinamide. It is known for its antithrombotic and anti-inflammatory properties, as well as its role in cancer cell metabolism.

Uses

Used in Analytical Chemistry:
3-Carbamylmethylpyridinium chloride is used as a standard in the quantification of 1-methylnicotinamide in urine samples using ion pairing reverse-phase high-performance liquid chromatography (RP-HPLC). This application aids in the assessment of MNA levels, which can provide insights into various physiological and pathological conditions.
Used in Pharmaceutical Research:
3-Carbamylmethylpyridinium chloride is utilized in the study of its antithrombotic and anti-inflammatory properties. It acts on the endothelium through the prostacyclin pathway and enhances nitric oxide bioavailability, making it a potential candidate for the development of therapeutic agents targeting cardiovascular and inflammatory diseases.
Used in Cancer Research:
3-Carbamylmethylpyridinium chloride is used in cancer research to investigate its role in cancer cell metabolism. Aggressive cancer cell lines have been reported to have higher levels of MNA, suggesting a potential link between 3-Carbamylmethylpyridinium chloride and the metabolic processes of cancer cells. This knowledge can contribute to the discovery of novel cancer therapies and diagnostic tools.

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.]

InChI:InChI=1/C7H9N2O.ClH/c1-9-4-2-3-6(5-9)7(8)10;/h2-5H,1H3,(H2,8,10);1H

Upstream product

• 98-92-0 nicotinamide 
• 19432-60-1 4-cyano-1,4-dihydro-N-methylpyridine-3-carboxamide 
• 6456-44-6 N-methylnicotineamide iodide 

Downstream Products

• 17750-23-1 1-methyl-1,4-dihydronicotinamide 
• 77837-12-8 1,6-dihydro-6-imino-1-methyl-3-pyridinecarboxamide 
• 6138-41-6 trigonelline hydrochloride 
• 701-44-0 1-methyl-2-pyridone-5-carboxamide 
• 19432-60-1 4-cyano-1,4-dihydro-N-methylpyridine-3-carboxamide 

Relevant articles and documents

Physical Organic Studies on Bimolecular Reactions in Reversed Micelles: Addition of Cyanide Ion to the N-Methyl-3-carbamoylpyridinium Ion in Hexadecyltrimethylammonium Bromide Reversed Micelles

The bimolecular reaction of cyanide (CN-) ion with N-methyl-3-carbamoylpyridinium (S+) ion, in the water pool of the reversed-micellar system water/ hexadecyltrimethylammonium bromide (HTAB)/ chloroform-isooctane (3:2, v/v) has been studied at various temperatures (15-40 deg C) by measuring spectrophotometrically the decrease of the absorption due to S+ (265 nm) and the increase of the absorption due to the addition product (340 nm).The results of the reaction series were examined throughout with respect to the molar ratio of water to HTAB, R.Since the rate and equilibrium constants of the bimolecular reaction are affected by the method in which the concentrations of reactants are defined or by fixing the extent of reaction space, the water pool is assumed to be the sole reaction space and the rate and equilibrium constants in the water pool, k2w and Kw, which are based on the modified concentrations of the reaction species, have been evaluated.It is found that terms of k2w and Kw, the smaller the value of R, the more the addition reaction is enhanced.From the relationships between Kw and k2w vs. temperature, the standard and activation enthalpies of reaction, ΔH and ΔH, respectively, have been calculated.The behavior of ΔH and ΔH as well as Kw and k2w is found to differ in reactions which have R below and above ca.3.To explain the enhancement of the reaction due to the specific field effect of the water pool and the retardation of the reaction due to electrostatic interactions among S+ ions, the involvement of CN- and HTAB ions is proposed.The differing behaviour in the reactions is more clearly manifested in the thermodynamic and kinetic diagrams of enthalpy vs. entropy, which give separate plots corresponding to R both below and above ca.3.In addition, the effect of varying the CN- ion concentration is discussed and is found to be consistent with the situation described above.

Direct observation of NADH radical cation generated in reactions with one-electron oxidants

The formation of NADH radical cation in reactions with one-electron oxidants was observed for the first time. Transient products involving two tautomeric (keto and enol) forms of radical cation and neutral radical were spectroscopically characterized by means of pulse radiolysis. The kinetics of the decay of keto radical cation and neutral radical was investigated. The pKa value of the enol form of NADH radical cation was determined. The simple analogues of NADH and NAD+, namely, 1-methyl-1,4-dihydronicotinamide and it oxidized form, were studied for comparison.