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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:36 UTC
Update Date2023-02-21 17:16:33 UTC
HMDB IDHMDB0003152
Secondary Accession Numbers
  • HMDB03152
Metabolite Identification
Common NameN-Methylnicotinamide
DescriptionN-methylnicotinamide is a pyridinecarboxamide that is nicotinamide in which one of the amide hydrogens is substituted by a methyl group. N-methylnicotinamide 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. (PMID:16207585 ). 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.
Structure
Thumb
Synonyms
ValueSource
3-(Methylcarbamoyl)pyridineChEBI
3-(N-Methylcarbamoyl)pyridineChEBI
N-Methyl nicotineamideChEBI
N-Methyl-3-pyridinecarboxamideChEBI
N-Methylpyridine-3-carboxamideChEBI
Nicotinic acid methylamideChEBI
Nicotinate methylamideGenerator
N -Methyl nicotineamideHMDB
N-METHYL-nicotinamideMeSH, HMDB
N-Methylnicotinamide monohydrochlorideMeSH, HMDB
Chemical FormulaC7H8N2O
Average Molecular Weight136.1512
Monoisotopic Molecular Weight136.063662888
IUPAC NameN-methylpyridine-3-carboxamide
Traditional NameN'methylnicotinamide
CAS Registry Number114-33-0
SMILES
CN=C(O)C1=CN=CC=C1
InChI Identifier
InChI=1S/C7H8N2O/c1-8-7(10)6-3-2-4-9-5-6/h2-5H,1H3,(H,8,10)
InChI KeyZYVXHFWBYUDDBM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Nicotinamide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point103.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.00HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothType 2 Diabetes details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL: A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiol Genomics. 2007 Apr 24;29(2):99-108. Epub 2006 Dec 26. [PubMed:17190852 ]
Associated OMIM IDs
DrugBank IDDB08840
Phenol Explorer Compound IDNot Available
FooDB IDFDB023115
KNApSAcK IDNot Available
Chemspider ID58476
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNicotinyl_methylamide
METLIN IDNot Available
PubChem Compound64950
PDB IDNot Available
ChEBI ID64399
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pumpo R, Sarnelli G, Spinella A, Budillon G, Cuomo R: The metabolism of nicotinamide in human liver cirrhosis: a study on N-methylnicotinamide and 2-pyridone-5-carboxamide production. Am J Gastroenterol. 2001 Apr;96(4):1183-7. [PubMed:11316167 ]
  2. Aleinik SI, Kodentsiva VM, Mitin IE, Sokol'nikov AA, Vrzhesinskaia OA, Isaeva VA, Terekhina TA, Stroganova AS, Erzhen K, Tsibul'skaia OA, et al.: [Effects of the use of a multivitamin preparation "Pikovit" (KRKA, Yugoslavia) on providing nursery children with vitamins]. Vopr Pitan. 1992 May-Jun;(3):14-9. [PubMed:1387494 ]
  3. Varnakova GM: [Use of nicotinamide for correcting the disordered nicotinic acid allowance of patients with noncoronarogenic heart diseases]. Vopr Pitan. 1983 Jul-Aug;(4):32-5. [PubMed:6226157 ]
  4. Cuomo R, Pumpo R, Sarnelli G, Capuano G, Budillon G: Nicotinamide methylation and hepatic energy reserve: a study by liver perfusion in vitro. J Hepatol. 1995 Oct;23(4):465-70. [PubMed:8655965 ]
  5. Pitche PT: [Pellagra]. Sante. 2005 Jul-Sep;15(3):205-8. [PubMed:16207585 ]
  6. Jiang N, Wang M, Song J, Liu Y, Chen H, Mu D, Xia M: N-methylnicotinamide protects against endothelial dysfunction and attenuates atherogenesis in apolipoprotein E-deficient mice. Mol Nutr Food Res. 2016 Jul;60(7):1625-36. doi: 10.1002/mnfr.201501019. Epub 2016 May 4. [PubMed:26887666 ]