You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Livestock Metabolome Database.
Record Information
Version1.0
Creation Date2016-07-13 19:41:47 UTC
Update Date2016-07-20 20:20:03 UTC
LmdbLMDB00073
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethylamine
DescriptionMethylamine 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 ).
Structure
Thumb
Synonyms
ValueSource
AminomethaneChEBI
CH3-NH2ChEBI
MeNH2ChEBI
MethanamineChEBI
MMAChEBI
MonomethylamineChEBI
Anhydrous methylamineHMDB
CarbinamineHMDB
ImizinHMDB
MercurialinHMDB
Methyl groupHMDB
Methyl OF gamma-N-methylasparagineHMDB
Methylamine anhydrousHMDB
Methylamine aqueous solutionHMDB
Methylamine solutionHMDB
Methylamine solutionsHMDB
MethylaminenHMDB
MetilamineHMDB
MetyloaminaHMDB
N-MethylamineHMDB
NMAHMDB
NMEHMDB
Methylamine ion (1-)HMDB
Methylamine nitrateHMDB
Methylamine perchlorateHMDB
Methylamine sulfate (1:1)HMDB
Methylamine sulfate (2:1)HMDB
Methylamine, 13C-labeledHMDB
Methylamine, 14C-labeledHMDB
Methylamine, 15N-labeledHMDB
Methylamine hydrobromideHMDB
Methylamine hydrochloride, 14C-labeledHMDB
Methylamine, cesium saltHMDB
Methylamine, monopotassium saltHMDB
MethylammoniumHMDB
Methylammonium ionHMDB
Methylamine hydroiodideHMDB
Methylamine, monosodium saltHMDB
Methylamine bisulfiteHMDB
Methylamine hydrideHMDB
Methylamine hydrochlorideHMDB
Methylamine hydrofluorideHMDB
Methylamine hydrogen cyanideHMDB
Monomethylammonium ionHMDB
Chemical FormulaCH5N
Average Molecular Weight31.0571
Monoisotopic Molecular Weight31.042199165
IUPAC Namemethanamine
Traditional Namemethylamine
CAS Registry Number74-89-5
SMILES
CN
InChI Identifier
InChI=1S/CH5N/c1-2/h2H2,1H3
InChI KeyBAVYZALUXZFZLV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentMonoalkylamines
Alternative Parents
Substituents
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.1ALOGPS
logP-0.63ChemAxon
logS1.07ALOGPS
pKa (Strongest Basic)10.08ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity9.92 m³·mol⁻¹ChemAxon
Polarizability3.86 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-50fb665f1ba89a03baf9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9000000000-93f5049fa2e67d0da26dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-53c64a174764bada8913Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-1c10568342e547416eafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-2910620cfb01718df17fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-2910620cfb01718df17fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-2910620cfb01718df17fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-f140127f4f4b677d2975Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-f140127f4f4b677d2975Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-f140127f4f4b677d2975Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-986b844d44ea8cab8877Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-986b844d44ea8cab8877Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-986b844d44ea8cab8877Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-d90d418cf76ae365e6c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-d90d418cf76ae365e6c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-d90d418cf76ae365e6c5Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-43b9d7b881c659f2ceb1Spectrum
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
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified34.3 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified136 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified202 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified608 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified28.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified89.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified108.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified703.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified213 +/- 32 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified445 +/- 44 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified489 +/- 63 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified14.75 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified23.86 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified17.53 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified108 +/- 104 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified49 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified49 +/- 12 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified703 +/- 119 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified85 +/- 72 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified90 +/- 33 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified2,240 +/- 150 uMNot AvailableCaprine details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
DrugBank IDDB01828
HMDB IDHMDB0000164
FooDB IDFDB003958
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1800349
BioCyc IDMETHYLAMINE
METLIN ID3767
PDB IDNot Available
Wikipedia LinkMethylamine
Chemspider ID6089
ChEBI ID16830
PubChem Compound ID6329
Kegg Compound IDC00218
YMDB IDNot Available
ECMDB IDECMDB00164
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pirisino R, Ghelardini C, De Siena G, Malmberg P, Galeotti N, Cioni L, Banchelli G, Raimondi L: Methylamine: a new endogenous modulator of neuron firing? Med Sci Monit. 2005 Aug;11(8):RA257-61. Epub 2005 Jul 25. [16049393 ]
  2. Yu PH, Wright S, Fan EH, Lun ZR, Gubisne-Harberle D: Physiological and pathological implications of semicarbazide-sensitive amine oxidase. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):193-9. [12686132 ]
  3. McDonald A, Tipton K, O'Sullivan J, Olivieri A, Davey G, Coonan AM, Fu W: Modelling the roles of MAO and SSAO in glucose transport. J Neural Transm (Vienna). 2007;114(6):783-6. Epub 2007 Apr 5. [17406961 ]