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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:56:01 UTC
HMDB IDHMDB0000699
Secondary Accession Numbers
  • HMDB00699
Metabolite Identification
Common Name1-Methylnicotinamide
Description1-Methylnicotinamide, also known as trigonellinamide or trigonellamide chloride, 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. 1-Methylnicotinamide exists in all living species, ranging from bacteria to plants to humans. 1-Methylnicotinamide has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 1-methylnicotinamide a potential biomarker for the consumption of these foods. 1-Methylnicotinamide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 1-Methylnicotinamide.
Structure
Thumb
Synonyms
Chemical FormulaC7H9N2O
Average Molecular Weight137.1592
Monoisotopic Molecular Weight137.07148792
IUPAC Name3-carbamoyl-1-methylpyridin-1-ium
Traditional Name1-methylnicotinamide
CAS Registry Number3106-60-3
SMILES
C[N+]1=CC=CC(=C1)C(N)=O
InChI Identifier
InChI=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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility855 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.099-0.851 uMAdult (>18 years old)BothCirrhosis details
UrineDetected and Quantified7.426 +/- 3.509 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified3.0 (0.0-14.0) umol/mmol creatinineAdult (>18 years old)BothLung cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected and Quantified37.00 (11.5-62.7) umol/mmol creatinineAdult (>18 years old)BothPellagra details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Somogyi A, Siebert D, Bochner F: Determination of endogenous concentrations of N1-methylnicotinamide in human plasma and urine by high-performance liquid chromatography. Anal Biochem. 1990 May 15;187(1):160-5. [PubMed:2142586 ]
Lung Cancer
  1. Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
Pellagra
  1. Creeke PI, Dibari F, Cheung E, van den Briel T, Kyroussis E, Seal AJ: Whole blood NAD and NADP concentrations are not depressed in subjects with clinical pellagra. J Nutr. 2007 Sep;137(9):2013-7. [PubMed:17709435 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 211980 (Lung Cancer)
  • 601313 (Autosomal dominant polycystic kidney disease)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDDB11710
Phenol Explorer Compound IDNot Available
FooDB IDFDB022188
KNApSAcK IDC00052106
Chemspider ID444
KEGG Compound IDC02918
BioCyc IDCPD-396
BiGG ID2226225
Wikipedia Link1-Methylnicotinamide
METLIN ID5667
PubChem Compound457
PDB IDNot Available
ChEBI ID16797
Food Biomarker OntologyNot Available
VMH ID1MNCAM
MarkerDB IDMDB00000225
Good Scents IDNot Available
References
Synthesis ReferenceNelis, 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.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
1-Methylnicotinamide + Oxygen + Water → N1-Methyl-4-pyridone-3-carboxamide + Hydrogen peroxide + Hydrogen Iondetails
1-Methylnicotinamide + Oxygen + Water → Nudifloramide + Hydrogen peroxide + Hydrogen Iondetails
General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the N-methylation of nicotinamide and other pyridines to form pyridinium ions. This activity is important for biotransformation of many drugs and xenobiotic compounds.
Gene Name:
NNMT
Uniprot ID:
P40261
Molecular weight:
29573.705
Reactions
S-Adenosylmethionine + Niacinamide → S-Adenosylhomocysteine + 1-Methylnicotinamidedetails
S-Adenosylmethionine + Niacinamide + Hydrogen Ion → S-Adenosylhomocysteine + 1-Methylnicotinamidedetails