1-Methylnicotinamide (CHEM021683)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:09:55 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021683
Identification
Common Name1-Methylnicotinamide
ClassSmall Molecule
DescriptionA pyridinium ion comprising nicotinamide having a methyl group at the 1-position. It is a metabolite of nicotinamide which was initially considered to be biologically inactive but has emerged as an anti-thrombotic and anti-inflammatory agent.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-Methyl nicotinamideChEBI
1-Methylnicotinamide cationChEBI
3-(Aminocarbonyl)-1-methylpyridiniumChEBI
3-Carbamoyl-1-methylpyridin-1-iumChEBI
N(1)-MethylnicotinamideChEBI
N-1-MethylnicotinamideChEBI
TrigonellinamideChEBI
1-Methyl-3-carbamoylpyridiniumHMDB
1-Methyl-3-carbamoylpyridinium cationHMDB
3-Amido-N-methylpyridinium: 1-methyl-3-pyridinecarboxamideHMDB
3-Carbamoyl-1-methyl-pyridiniumHMDB
I-methyl nicotinamideHMDB
N'-methylnicotinamideHMDB
N'MethylnicotinamideHMDB
N-Methyl-3-carbamidopyridiniumHMDB
N-Methyl-3-carbamoylpyridinium ionHMDB
N1-MethylnicotinamideHMDB
N(1)-Methylnicotinamide chlorideHMDB
N(1)-Methylnicotinamide cyanideHMDB
N(1)-Methylnicotinamide fluorideHMDB
N(1)-Methylnicotinamide iodide, 3-(aminocarbonyl-13C)-labeledHMDB
N(1)-Methylnicotinamide methylsulfateHMDB
N(1)-Methylnicotinamide perchlorateHMDB
N(1)-Methylnicotinamide bromideHMDB
N(1)-Methylnicotinamide iodideHMDB
N(1)-Methylnicotinamide tetrafluoroborate (1-)HMDB
Trigonellamide chlorideHMDB
Chemical FormulaC7H9N2O
Average Molecular Mass137.159 g/mol
Monoisotopic Mass137.071 g/mol
CAS Registry Number3106-60-3
IUPAC Name3-carbamoyl-1-methylpyridin-1-ium
Traditional Name1-methylnicotinamide
SMILESC[N+]1=CC=CC(=C1)C(N)=O
InChI IdentifierInChI=1S/C7H8N2O/c1-9-4-2-3-6(5-9)7(8)10/h2-5H,1H3,(H-,8,10)/p+1
InChI KeyLDHMAVIPBRSVRG-UHFFFAOYSA-O
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
  • N-methylpyridinium
  • Pyridinium
  • Heteroaromatic compound
  • Vinylogous amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP-3.7ALOGPS
logP-4.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)12.24ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.97 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5900000000-5a5fd45836c387d92371Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-c99e0e70357eb6fa74bbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-93675f2b9efbaba4d471Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fvl-9000000000-b1e908db583e418c2545Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-000i-0900000000-9c3104d60f21f6375b0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-000i-1900000000-e500f262d42edb9b3ad7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9200000000-496b2cf62a07bea4f746Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-002f-9000000000-a17b3a63979577f6fa9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00ou-9000000000-46a856cd097a7a14dc90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000l-6900000000-360fb882a925f7e9edc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-0006-9000000000-babd4e89db309a5c74cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0900000000-9c3104d60f21f6375b0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-1900000000-e500f262d42edb9b3ad7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9200000000-052c844f974abba065ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002f-9000000000-a17b3a63979577f6fa9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00ou-9000000000-2fe6c195129f32a62a3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000l-6900000000-360fb882a925f7e9edc9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-9000000000-babd4e89db309a5c74cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0900000000-08a578fa81c8d41a4fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-d889aade6d1014ffb393Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-1900000000-8052aba6067c868e594fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9500000000-579bc8310420ec3d8786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-141e3a418b748abf9e1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-33499eeb5abff5a8b53bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-e45f804a013c97310f00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-5527bd16347dfbb8af1bSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11710
HMDB IDHMDB0000699
FooDB IDFDB022188
Phenol Explorer IDNot Available
KNApSAcK IDC00052106
BiGG ID2226225
BioCyc IDCPD-396
METLIN ID5667
PDB IDNot Available
Wikipedia Link1-Methylnicotinamide
Chemspider ID444
ChEBI ID16797
PubChem Compound ID457
Kegg Compound IDC02918
YMDB IDYMDB00348
ECMDB IDECMDB24052
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10644906
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11199218
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11952169
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12829005
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12856834
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=145178
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=160917
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16197374
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17641676
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17826027
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=18373238
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18953089
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19307696
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22932811
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=25129409
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25552403
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=26066674
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=26115505
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=28443021
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28720493
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=33317539
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=33442746
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=33523930
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=6215856
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=6448542
27. Nelis, Hans J. C. F.; Airy, Subhash C.; Sinsheimer, J. E. Comparison of the alkylation of nicotinamide and 4-(p-nitrobenzyl)pyridine for the determination of aliphatic epoxides. Analytical Chemistry (1982), 54(2), 213-16.
28. Pelletier O, Brassard R: Automated and manual determination of N1-methylnicotinamide in urine. Am J Clin Nutr. 1977 Dec;30(12):2108-16.
29. Carter EG: Quantitation of urinary niacin metabolites by reversed-phase liquid chromatography. Am J Clin Nutr. 1982 Nov;36(5):926-30.
30. Slominska EM, Smolenski RT, Szolkiewicz M, Leaver N, Rutkowski B, Simmonds HA, Swierczynski J: Accumulation of plasma N-methyl-2-pyridone-5-carboxamide in patients with chronic renal failure. Mol Cell Biochem. 2002 Feb;231(1-2):83-8.
31. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.
32. Patterson JI, Brown RR, Linkswiler H, Harper AE: Excretion of tryptophan-niacin metabolites by young men: effects of tryptophan, leucine, and vitamin B6 intakes. Am J Clin Nutr. 1980 Oct;33(10):2157-67.
33. Musfeld C, Biollaz J, Belaz N, Kesselring UW, Decosterd LA: Validation of an HPLC method for the determination of urinary and plasma levels of N1-methylnicotinamide, an endogenous marker of renal cationic transport and plasma flow. J Pharm Biomed Anal. 2001 Jan;24(3):391-404.
34. Wozniacka A, Wieczorkowska M, Gebicki J, Sysa-Jedrzejowska A: Topical application of 1-methylnicotinamide in the treatment of rosacea: a pilot study. Clin Exp Dermatol. 2005 Nov;30(6):632-5.
35. Chlopicki S, Swies J, Mogielnicki A, Buczko W, Bartus M, Lomnicka M, Adamus J, Gebicki J: 1-Methylnicotinamide (MNA), a primary metabolite of nicotinamide, exerts anti-thrombotic activity mediated by a cyclooxygenase-2/prostacyclin pathway. Br J Pharmacol. 2007 Sep;152(2):230-9. Epub 2007 Jul 16.
36. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.