Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H8N2O |
| Molecular Weight | 136.1512 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)C1=CN=CC=C1
InChI
InChIKey=ZYVXHFWBYUDDBM-UHFFFAOYSA-N
InChI=1S/C7H8N2O/c1-8-7(10)6-3-2-4-9-5-6/h2-5H,1H3,(H,8,10)
| Molecular Formula | C7H8N2O |
| Molecular Weight | 136.1512 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Nicotinyl methylamide (N-methylnicotinamide) is an experimental drug with no approved indication or marketed formulation. Nicotinyl methylamide is a metabolite of niacin (or nicotinamide) and is commonly found in human urine. However low levels of urinary excretion of N-methylnicotinamide indicates niacin deficiency. In patients with liver cirrhosis nicotinamide methylation is increased leading to a rise in urinary N-methylnicotinamide. The hyperfunction of this methylating pathway might play a protective role against the toxic effect of intracellular accumulation of nicotinamide deriving from the catabolic state of cirrhosis. N-methylnicotinamide is known to inhibit choline transport and reduce choline clearance out of the brain. N-methylnicotinamide has been found to be a microbial metabolite. N-methylnicotinamide inhibits arterial thrombosis in hypertensive rats. N-methylnicotinamide via production/release of prostacyclin inhibits arterial thrombosis development. The antithrombotic effect of N-methylnicotinamide is accompanied by platelet inhibition and enhanced fibrinolysis, due to the decrease production of plasminogen activator inhibitor -1.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10037454
Curator's Comment: Nicotinyl methylamide does not cross the blood-brain barrier.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles. | 2011-08 |
|
| An insight into the metabolic responses of ultra-small superparamagnetic particles of iron oxide using metabonomic analysis of biofluids. | 2010-10-01 |
|
| A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. | 2010-09 |
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| Effect of taurine supplementation on hyperhomocysteinemia and markers of oxidative stress in high fructose diet induced insulin resistance. | 2010-06-30 |
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| Urinary metabolic phenotyping differentiates children with autism from their unaffected siblings and age-matched controls. | 2010-06-04 |
|
| Protective effect of nicotinamide against poly(ADP-ribose) polymerase-1-mediated astrocyte death depends on its transporter-mediated uptake. | 2010-04-24 |
|
| Diaqua-bis(5-bromo-2-hydroxy-benzoato)bis-(N-methyl-nicotinamide)zinc(II). | 2010-03-13 |
|
| Identification of hypoxanthine as a urine marker for non-Hodgkin lymphoma by low-mass-ion profiling. | 2010-02-23 |
|
| Development of a hydrophilic liquid interaction chromatography-high-performance liquid chromatography-tandem mass spectrometry based stable isotope dilution analysis and pharmacokinetic studies on bioactive pyridines in human plasma and urine after coffee consumption. | 2010-02-15 |
|
| A metabonomic comparison of urinary changes in Zucker and GK rats. | 2010 |
|
| Nicotinamide and its metabolite N-methylnicotinamide increase skin vascular permeability in rats. | 2009-04 |
|
| Carrier-mediated uptake of 1-(2-methoxyethyl)-2-methyl-4,9-dioxo-3-(pyrazin-2-ylmethyl)-4,9-dihydro-1H-naphtho[2,3-d]imidazolium bromide (YM155 monobromide), a novel small-molecule survivin suppressant, into human solid tumor and lymphoma cells. | 2009-03 |
|
| Gastroduodenal mucosal defense. | 2008-12 |
|
| Development of oxidative stress by cytochrome P450 induction in rodents is selective for barbiturates and related to loss of pyridine nucleotide-dependent protective systems. | 2008-06-20 |
|
| Dietary and genetic compromise in folate availability reduces acetylcholine, cognitive performance and increases aggression: critical role of S-adenosyl methionine. | 2008-04 |
|
| N-methylnicotinamide failed to induce endothelial prostacyclin release in perfused rat hindquarters. | 2008-01-15 |
|
| Nitroso-imidacloprid irreversibly inhibits rabbit aldehyde oxidase. | 2007-12 |
|
| 1-Methylnicotinamide stimulates cell growth and inhibits hemoglobin synthesis in differentiating murine erythroleukemia cells. | 2007-12 |
|
| Effect of dronedarone on renal function in healthy subjects. | 2007-12 |
|
| Metabonomics evaluations of age-related changes in the urinary compositions of male Sprague Dawley rats and effects of data normalization methods on statistical and quantitative analysis. | 2007-11-01 |
|
| Functional characterization of testis-specific rodent multidrug and toxic compound extrusion 2, a class III MATE-type polyspecific H+/organic cation exporter. | 2007-11 |
|
| N-methylnicotinamide inhibits arterial thrombosis in hypertensive rats. | 2007-09 |
|
| The comparative bioavailability of an extended-release niacin and lovastatin fixed dose combination tablet versus extended-release niacin tablet, lovastatin tablet and a combination of extended-release niacin tablet and lovastatin tablet. | 2007-09 |
|
| Plasma and urine pharmacokinetics of niacin and its metabolites from an extended-release niacin formulation. | 2007-08 |
|
| Effect of the rate of niacin administration on the plasma and urine pharmacokinetics of niacin and its metabolites. | 2007-06 |
|
| Niacin nutritional status in HIV type 1-positive children: preliminary data. | 2007-05 |
|
| A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. | 2007-04-24 |
|
| Beyond lipids, pharmacological PPARalpha activation has important effects on amino acid metabolism as studied in the rat. | 2007-04 |
|
| Changes in vitamin status of Indian Antarctic expeditioners during a one-month stay in Austral Summer. | 2007 |
|
| 1H-NMR metabolic profiling of human neonatal urine. | 2006-12 |
|
| A metabonomics study of the hepatotoxicants galactosamine, methylene dianiline and clofibrate in rats. | 2006-09 |
|
| Characteristics of thiamine uptake by the BeWo human trophoblast cell line. | 2006-07-31 |
|
| Effect of standard nicotinamide in the prevention of type 1 diabetes in first degree relatives of persons with type 1 diabetes. | 2006-06 |
|
| Tetraethylammonium and nicotine transport by the Malpighian tubules of insects. | 2006-05 |
|
| Molecular tweezer and clip in aqueous solution: unexpected self-assembly, powerful host-guest complex formation, quantum chemical 1H NMR shift calculation. | 2006-04-12 |
|
| The regulation and inhibition of 17beta-hydroxysteroid dehydrogenase in breast cancer. | 2006-03-27 |
|
| Evaluation of volatile ion-pair reagents for the liquid chromatography-mass spectrometry analysis of polar compounds and its application to the determination of methadone in human plasma. | 2006-02-24 |
|
| Liquid chromatographic/mass spectrometric procedure for measurement of NAD catabolites in human and rat plasma and urine. | 2006 |
|
| [Pellagra]. | 2005-10-07 |
|
| Electron transfer within complex II. Succinate:ubiquinone oxidoreductase of Escherichia coli. | 2005-09-30 |
|
| Molecular and functional characterization of an Na+-independent choline transporter in rat astrocytes. | 2005-09 |
|
| Increased tubular organic ion clearance following chronic ACE inhibition in patients with type 1 diabetes. | 2005-06 |
|
| Tryptophan-NAD+ pathway metabolites as putative biomarkers and predictors of peroxisome proliferation. | 2005-04 |
|
| Development of a multivariate statistical model to predict peroxisome proliferation in the rat, based on urinary 1H-NMR spectral patterns. | 2005-03-15 |
|
| Parkinson's disease: the first common neurological disease due to auto-intoxication? | 2005-03 |
|
| Identification of aldehyde oxidase as the neonicotinoid nitroreductase. | 2005-02 |
|
| Nicotinamide homeostasis: a xenobiotic pathway that is key to development and degenerative diseases. | 2005 |
|
| The effect of a series of organic cations upon the plasmalemmal serotonin transporter, SERT. | 2004-11-19 |
|
| Nicotinamide methylation and hepatic energy reserve: a study by liver perfusion in vitro. | 1995-10 |
|
| [Use of nicotinamide for correcting the disordered nicotinic acid allowance of patients with noncoronarogenic heart diseases]. | 1983-07-01 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:41:11 GMT 2025
by
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on
Mon Mar 31 21:41:11 GMT 2025
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| Record UNII |
X3I82S5L8I
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| Record Status |
Validated (UNII)
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C008472
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CHEMBL11978
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204-046-4
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NICOTINYL METHYLAMIDE
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100000090088
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ACTIVE MOIETY |