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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 15:12:36 UTC
Update Date2021-09-07 16:45:34 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
Data?1582752264
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
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
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
Disposition

Biological location

Source

Route of exposure

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 Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP10(0.65) g/LALOGPS
logP10(-0.17) g/LChemAxon
logS10(-1.7) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.70931661259
DarkChem[M-H]-124.7131661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylnicotinamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2900000000-94cc770fe8f431a31a232017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylnicotinamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylnicotinamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOFsplash10-001i-9400000000-8e4f49b47197c2f4950a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOFsplash10-000i-1900000000-2152d45cdd5d4a662a0d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOFsplash10-0ue9-9000000000-56e1f859bab88518e2342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOFsplash10-000i-1900000000-9ca26f496c6a3a243dd02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOFsplash10-0ue9-9000000000-b8d9c720208f33d565542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOFsplash10-001i-9300000000-0c8c3a9a6ea309d68dcd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 20V, Negative-QTOFsplash10-004i-9000000000-388b45f56c914aef2c662021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 10V, Negative-QTOFsplash10-004i-9100000000-5a24140875f7746c8f252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Methylnicotinamide 40V, Negative-QTOFsplash10-0ufr-9000000000-9e2091f72eb24ecdce6c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOFsplash10-000i-0900000000-dfdfbb6805540661146c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOFsplash10-000i-2900000000-a85e482755a0e7a2fbbb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOFsplash10-0kai-9100000000-c695203a7da9f4d2ee3e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Negative-QTOFsplash10-000i-0900000000-0ccdb864a51adc6731d72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Negative-QTOFsplash10-052r-3900000000-aa587304320e04d3f4ef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Negative-QTOFsplash10-004i-9000000000-458b5a3c154373324d862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Negative-QTOFsplash10-004r-9600000000-8c19f57e019ee89463af2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Negative-QTOFsplash10-004i-9000000000-c2850ce6846335b0374d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Negative-QTOFsplash10-004i-9000000000-d55af7b467802be46f892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 10V, Positive-QTOFsplash10-000i-0900000000-f77bf0c7af614dc227052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 20V, Positive-QTOFsplash10-06sr-9800000000-642378e25bf582bc8ff22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylnicotinamide 40V, Positive-QTOFsplash10-0fb9-9000000000-01d687f29b752dd7b2932021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
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)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 ]
  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 ]