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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
Structure of NICOTINYL METHYLAMIDE

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)

HIDE SMILES / InChI

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

Curator's Comment: Nicotinyl methylamide does not cross the blood-brain barrier.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
Effect of taurine supplementation on hyperhomocysteinemia and markers of oxidative stress in high fructose diet induced insulin resistance.
2010-06-30
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 Mon Mar 31 21:41:11 GMT 2025
Edited
by admin
on Mon Mar 31 21:41:11 GMT 2025
Record UNII
X3I82S5L8I
Record Status Validated (UNII)
Record Version
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Name Type Language
NICOTINYL METHYLAMIDE
Systematic Name English
NSC-66521
Preferred Name English
3-(METHYLCARBAMOYL)PYRIDINE
Systematic Name English
NICOTINIC ACID METHYLAMIDE
Systematic Name English
3-(N-METHYLCARBAMOYL)PYRIDINE
Systematic Name English
N'-METHYLNICOTINAMIDE
Common Name English
3-PYRIDINECARBOXAMIDE, N-METHYL-
Systematic Name English
SR-4415
Code English
N-METHYLNICOTINAMIDE
Systematic Name English
N-METHYL-3-PYRIDINECARBOXAMIDE
Systematic Name English
NICOTINAMIDE, N-METHYL-
Systematic Name English
Classification Tree Code System Code
WHO-ATC A05AB01
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
WHO-VATC QA05AB01
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
Code System Code Type Description
MESH
C008472
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID00870467
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
DRUG BANK
DB08840
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
DRUG CENTRAL
4862
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL11978
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
NSC
66521
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
PUBCHEM
64950
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
CHEBI
64399
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
CAS
114-33-0
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-046-4
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
WIKIPEDIA
NICOTINYL METHYLAMIDE
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
SMS_ID
100000090088
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
FDA UNII
X3I82S5L8I
Created by admin on Mon Mar 31 21:41:11 GMT 2025 , Edited by admin on Mon Mar 31 21:41:11 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY