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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
[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
[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
Evidence for a carrier-mediated mechanism for thiamine transport to human jejunal basolateral membrane vesicles.
2003 Jan
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
Development of a multivariate statistical model to predict peroxisome proliferation in the rat, based on urinary 1H-NMR spectral patterns.
2004 Jul-Oct
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
The effect of a series of organic cations upon the plasmalemmal serotonin transporter, SERT.
2004 Nov 19
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
Tryptophan-NAD+ pathway metabolites as putative biomarkers and predictors of peroxisome proliferation.
2005 Apr
Identification of aldehyde oxidase as the neonicotinoid nitroreductase.
2005 Feb
[Pellagra].
2005 Jul-Sep
Increased tubular organic ion clearance following chronic ACE inhibition in patients with type 1 diabetes.
2005 Jun
Parkinson's disease: the first common neurological disease due to auto-intoxication?
2005 Mar
Molecular and functional characterization of an Na+-independent choline transporter in rat astrocytes.
2005 Sep
Electron transfer within complex II. Succinate:ubiquinone oxidoreductase of Escherichia coli.
2005 Sep 30
Liquid chromatographic/mass spectrometric procedure for measurement of NAD catabolites in human and rat plasma and urine.
2006
Molecular tweezer and clip in aqueous solution: unexpected self-assembly, powerful host-guest complex formation, quantum chemical 1H NMR shift calculation.
2006 Apr 12
1H-NMR metabolic profiling of human neonatal urine.
2006 Dec
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
Characteristics of thiamine uptake by the BeWo human trophoblast cell line.
2006 Jul 31
Effect of standard nicotinamide in the prevention of type 1 diabetes in first degree relatives of persons with type 1 diabetes.
2006 Jun
The regulation and inhibition of 17beta-hydroxysteroid dehydrogenase in breast cancer.
2006 Mar 27
Tetraethylammonium and nicotine transport by the Malpighian tubules of insects.
2006 May
Beyond lipids, pharmacological PPARalpha activation has important effects on amino acid metabolism as studied in the rat.
2007 Apr
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human.
2007 Apr 24
Plasma and urine pharmacokinetics of niacin and its metabolites from an extended-release niacin formulation.
2007 Aug
Nitroso-imidacloprid irreversibly inhibits rabbit aldehyde oxidase.
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
Niacin nutritional status in HIV type 1-positive children: preliminary data.
2007 May
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
Changes in vitamin status of Indian Antarctic expeditioners during a one-month stay in Austral Summer.
2007 Winter
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 Jun 20
Nicotinamide and its metabolite N-methylnicotinamide increase skin vascular permeability in rats.
2009 Apr
A metabonomic comparison of urinary changes in Zucker and GK rats.
2010
Protective effect of nicotinamide against poly(ADP-ribose) polymerase-1-mediated astrocyte death depends on its transporter-mediated uptake.
2010 Apr 24
Identification of hypoxanthine as a urine marker for non-Hodgkin lymphoma by low-mass-ion profiling.
2010 Feb 23
Effect of taurine supplementation on hyperhomocysteinemia and markers of oxidative stress in high fructose diet induced insulin resistance.
2010 Jun 30
Urinary metabolic phenotyping differentiates children with autism from their unaffected siblings and age-matched controls.
2010 Jun 4
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:15:35 GMT 2023
Edited
by admin
on Sat Dec 16 07:15:35 GMT 2023
Record UNII
X3I82S5L8I
Record Status Validated (UNII)
Record Version
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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
PRIMARY
DRUG BANK
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
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
PRIMARY
ChEMBL
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
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
Related Record Type Details
PARENT -> METABOLITE ACTIVE
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY