Basic information
- CAS
701-44-0- Standard SMILES
Cn1cc(C(N)=O)ccc1=O- InChIKey
JLQSXXWTCJPCBC-UHFFFAOYSA-N- Molecular formula
- C7H8N2O2
- Average molar mass
- 152.15 g/mol
- Monoisotopic mass
- 152.0585775
Overview
N-methyl-6-pyridone-3-carboxamide is a pyridone that is 2-pyridone substituted with a carboxamide group at C-5 and a methyl group at N-1. It has a role as a metabolite and a mouse metabolite. It is a member of methylpyridines, a pyridinecarboxamide and a pyridone.
Names & identifiers
- Preferred name
- N1-Methyl-2-pyridone-5-carboxamide
- IUPAC
- 1-methyl-6-oxopyridine-3-carboxamide
- English name
- 1-methyl-6-oxo-pyridine-3-carboxamide
- Molecular formula
- C7H8N2O2
- Molecular weight
- 152.15
Names & synonyms
Nudifloramide701-44-01-methyl-6-oxo-1,6-dihydropyridine-3-carboxamideN1-Methyl-2-pyridone-5-carboxamideN'-Methyl-2-pyridone-5-carboxamide1-Methyl-5-carboxylamide-2-pyridone3-Pyridinecarboxamide, 1,6-dihydro-1-methyl-6-oxo-DTXSID7022037468139USC7WN(1)-methyl-2-pyridone-5-carboxamideRefChem:831461DTXCID70142865
Show more names
2-PyN-methyl-6-pyridone-3-carboxamide1-Methyl-6-oxo-1,6-dihydronicotinamideNicotinamide Impurity 6（Nedifloramide）1-Methyl 6-oxo-1,6-dihydro-3-pyridinecarboxamide
1-methyl-6-oxopyridine-3-carboxamideN-methyl-2-pyridone-5-carboxamideMFCD004572831-METHYL-6-OXO-PYRIDINE-3-CARBOXAMIDE2PY3-Carbamoyl-1-methyl-6-pyridoneN-Me-2PY1,6-Dihydro-1-methyl-6-oxonicotinamide
Database identifiers
- CAS
701-44-0- PubChem CID
- 69698
Properties
Computed structural properties
- XLogP
- -1
- Topological polar surface area
- 63.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 266
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section132.1 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 202 · 202-207°C (dec.)
- Boiling point
- 396.7 · 396.7±42.0 °C(Predicted)
- Density
- 1.3 · 1.300±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Solid
- pka
- 14.46 · 14.46±0.20(Predicted)
- color
- White to Light Brown
- InChI
- 1S/C7H8N2O2/c1-9-4-5(7(8)11)2-3-6(9)10/h2-4H,1H3,(H2,8,11)
- InChIKey
- JLQSXXWTCJPCBC-UHFFFAOYSA-N
- SMILES
- [n]1([c](ccc(c1)C(=O)N)=O)C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P260, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary
Uremic toxins such as N-methyl-2-pyridone-5-carboxamide are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).
Chemistry & industry
Pharmacology
Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Tissue LocationsPlacenta
Cellular LocationsCytoplasm
Metabolite PathwaysNicotinate and nicotinamide metabolism
Uses & manufacturing
UsesNaturally produced by the body (endogenous).
Applications
DescriptionNudifloramide, known more commonly as N-methyl-2-pyridone-5-carboxamide (2-Py), is a metabolite of niacin via nicotinamide. It can be measured in serum and urine as part of metabolomic studies of niacin or nicotinamide intake and usage. Circulating levels of nudifloramide can be elevated and associated with toxic effects in patients receiving supplemental nicotinamide.
UsesNudifloramide is a metabolite of Niacin (or Nicorinic acid).
Upstream & downstream products
Upstream raw materials
Suppliers
Related reactions
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Compound notes
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