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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:36 UTC
Update Date2017-12-07 01:50:36 UTC
HMDB IDHMDB0003152
Secondary Accession Numbers
  • HMDB03152
Metabolite Identification
Common NameN-Methylnicotinamide
DescriptionN-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.
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
N-Methylnicotinamide monohydrochlorideMeSH
Chemical FormulaC7H8N2O
Average Molecular Weight136.1512
Monoisotopic Molecular Weight136.063662888
IUPAC NameN-methylpyridine-3-carboxamide
Traditional NameN'methylnicotinamide
CAS Registry Number114-33-0
SMILES
CNC(=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
DescriptionThis compound belongs to the class of chemical entities known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point103.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.21ALOGPS
logP-0.17ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)13.75ChemAxon
pKa (Strongest Basic)3.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.88 m³·mol⁻¹ChemAxon
Polarizability13.87 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2900000000-94cc770fe8f431a31a23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-dfdfbb6805540661146cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-a85e482755a0e7a2fbbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-9100000000-c695203a7da9f4d2ee3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-0ccdb864a51adc6731d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-3900000000-aa587304320e04d3f4efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-458b5a3c154373324d86View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected but not Quantified Adult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected but not Quantified Adult (>18 years old)BothType 2 Diabetes details
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023115
    KNApSAcK IDNot Available
    Chemspider ID58476
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound64950
    PDB IDNot Available
    ChEBI ID64399
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    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 ]