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Bovine Metabolome Database

Showing metabocard for Methylamine (BMDB00164)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:43
Accession Number BMDB00164
Common Name Methylamine
Description Methylamine occurs endogenously from amine catabolism and its tissue levels increase in some pathological conditions, including diabetes. Interestingly, methylamine and ammonia levels are reciprocally controlled by a semicarbazide-sensitive amine oxidase activity that deaminates methylamine to formaldehyde with the production of ammonia and hydrogen peroxide. Methylamine also targets the voltage-operated neuronal potassium channels, probably inducing release of neurotransmitter(s). Semicarbazide-sensitive amine oxidase (SSAO) catalyzes the deamination of primary amines. Such deamination has been shown capable of regulating glucose transport in adipose cells. It has been independently discovered that the primary structure of vascular adhesion protein-1 (VAP-1) is identical to SSAO. Increased serum SSAO activities have been found in patients with diabetic mellitus, vascular disorders and Alzheimer's disease. The SSAO-catalyzed deamination of endogenous substrates like methylamine led to production of toxic formaldehyde. Chronic elevated methylamine increases the excretion of malondialdehyde and microalbuminuria. Amine oxidase substrates such as methylamine have been shown to stimulate glucose uptake by increasing the recruitment of the glucose transporter GLUT4 from vesicles within the cell to the cell surface. Inhibition of this effect by the presence of semicarbazide and catalase led to the suggestion that the process is mediated by the H (2) O (2) produced in the oxidation of these amines. (PMID: 16049393, 12686132, 17406961)
  1. Aminomethane
  2. Anhydrous methylamine
  3. Carbinamine
  4. Imizin
  5. Mercurialin
  6. Methanamine
  7. Methyl group
  8. Methyl of gamma-n-methylasparagine
  9. Methylamine
  10. Methylamine anhydrous
  11. Methylamine aqueous solution
  12. Methylamine solution
  13. Methylamine solutions
  14. Methylaminen
  15. Metilamine
  16. Metyloamina
  17. MMA
  18. Monomethylamine
  19. N-methylamine
  20. NMA
  21. NME
Chemical IUPAC Name methanamine
Chemical Formula CH5N
Chemical Structure Structure
Chemical Taxonomy
  • Organic
Super Class
  • Amines
  • Aliphatic and Aryl Amines
Sub Class
  • Tertiary aliphatic amines
  • Mammalian_Metabolite
  • primary amine; primary aliphatic amine (alkylamine)
  • Endogenous
Average Molecular Weight 31.057
Monoisotopic Molecular Weight 31.042198
Isomeric SMILES CN
Canonical SMILES CN
KEGG Compound ID C00218 Link Image
BioCyc ID CPD-4521 Link Image
BiGG ID 1800349 Link Image
Wikipedia Link Methylamine Link Image
METLIN ID 3767 Link Image
PubChem Compound 6329 Link Image
PubChem Substance 826516 Link Image
ChEBI ID 16830 Link Image
CAS Registry Number 74-89-5
InChI Identifier InChI=1/CH5N/c1-2/h2H2,1H3
Synthesis Reference Denham, William S.; Knapp, Lionel F. The preparation of methylamine from ammonium methyl sulfate. Journal of the Chemical Society, Transactions (1920), 117 236-47.
Melting Point (Experimental) -93.4 oC
Experimental Water Solubility 1080 mg/mL at 25 oC [SCHWEIZER,AE et al. (1978)] Source: PhysProp
Predicted Water Solubility 367.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 1
State Liquid
Experimental LogP/Hydrophobicity -0.57 [HANSCH,C ET AL. (1995)] Source: PhysProp
Predicted LogP/Hydrophobicity -1.06 [Predicted by ALOGPS]; -0.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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2D Structure
3D Structure
Experimental PDB ID 1U7C Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 28.51 +/- 12 uM
Age N/A
Sex N/A
Condition Normal
Comments Not Available
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Biofluid Rumen
Value 703.35 +/- 114.8 uM
Age N/A
Sex N/A
Condition Rumen acidosis
Comments Not Available
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image