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)
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 |
---|---|---|
[Use of nicotinamide for correcting the disordered nicotinic acid allowance of patients with noncoronarogenic heart diseases]. | 1983 Jul-Aug |
|
[Effects of the use of a multivitamin preparation "Pikovit" (KRKA, Yugoslavia) on providing nursery children with vitamins]. | 1992 May-Jun |
|
Nicotinamide methylation and hepatic energy reserve: a study by liver perfusion in vitro. | 1995 Oct |
|
Copper complexes with bioactive ligands Part I--Antimicrobial activity. | 2001 |
|
Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects. | 2001 |
|
Transport of [3H]MPP+ in an immortalized rat brain microvessel endothelial cell line (RBE 4). | 2001 Jan |
|
Copper complexes with bioactive ligands. Part II--Antifungal activity. | 2002 |
|
[Connection between changing the vitamin and immune status and the character of the throat microflora in patients with chronic tonsillitis]. | 2003 |
|
Molecular tweezers and clips as synthetic receptors. Molecular recognition and dynamics in receptor-substrate complexes. | 2003 Dec |
|
Reduced tubular cation transport in diabetes: prevented by ACE inhibition. | 2003 Jun |
|
Potential urinary and plasma biomarkers of peroxisome proliferation in the rat: identification of N-methylnicotinamide and N-methyl-4-pyridone-3-carboxamide by 1H nuclear magnetic resonance and high performance liquid chromatography. | 2003 May-Aug |
|
Effects of feeding and body weight loss on the 1H-NMR-based urine metabolic profiles of male Wistar Han rats: implications for biomarker discovery. | 2004 Mar-Apr |
|
The role of advanced glycation in reduced organic cation transport associated with experimental diabetes. | 2004 Nov |
|
Niacin metabolite excretion in alcoholic pellagra and AIDS patients with and without diarrhea. | 2004 Sep |
|
Nicotinamide homeostasis: a xenobiotic pathway that is key to development and degenerative diseases. | 2005 |
|
[Pellagra]. | 2005 Jul-Sep |
|
Molecular and functional characterization of an Na+-independent choline transporter in rat astrocytes. | 2005 Sep |
|
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 Feb 24 |
|
Tetraethylammonium and nicotine transport by the Malpighian tubules of insects. | 2006 May |
|
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. | 2007 Apr 24 |
|
1-Methylnicotinamide stimulates cell growth and inhibits hemoglobin synthesis in differentiating murine erythroleukemia cells. | 2007 Dec |
|
Effect of dronedarone on renal function in healthy subjects. | 2007 Dec |
|
Effect of the rate of niacin administration on the plasma and urine pharmacokinetics of niacin and its metabolites. | 2007 Jun |
|
N-methylnicotinamide inhibits arterial thrombosis in hypertensive rats. | 2007 Sep |
|
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 Sep |
|
N-methylnicotinamide failed to induce endothelial prostacyclin release in perfused rat hindquarters. | 2008 Nov-Dec |
|
A metabonomic comparison of urinary changes in Zucker and GK rats. | 2010 |
|
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 Feb 15 |
|
Diaqua-bis(5-bromo-2-hydroxy-benzoato)bis-(N-methyl-nicotinamide)zinc(II). | 2010 Mar 13 |
|
An insight into the metabolic responses of ultra-small superparamagnetic particles of iron oxide using metabonomic analysis of biofluids. | 2010 Oct 1 |
|
A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. | 2010 Sep |
|
Characterization of organic anion-transporting polypeptide (Oatp) 1a1 and 1a4 null mice reveals altered transport function and urinary metabolomic profiles. | 2011 Aug |
Name | Type | Language | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
A05AB01
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
||
|
WHO-VATC |
QA05AB01
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C008472
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
DTXSID00870467
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
DB08840
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
4862
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
CHEMBL11978
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
66521
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
64950
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
64399
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
114-33-0
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
204-046-4
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
NICOTINYL METHYLAMIDE
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
100000090088
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY | |||
|
X3I82S5L8I
Created by
admin on Sat Dec 16 07:15:35 GMT 2023 , Edited by admin on Sat Dec 16 07:15:35 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)
PARENT (METABOLITE)