U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
[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
NICOTINYL METHYLAMIDE
Systematic 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
NSC-66521
Code English
NICOTINAMIDE, N-METHYL-
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
MESH
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
EPA CompTox
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
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DRUG BANK
DB08840
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DRUG CENTRAL
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
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ChEMBL
CHEMBL11978
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NSC
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
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PUBCHEM
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
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CHEBI
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
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CAS
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
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ECHA (EC/EINECS)
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
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WIKIPEDIA
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
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SMS_ID
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
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FDA UNII
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
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