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Record Information
Version1.0
Creation Date2016-09-30 22:20:25 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0000164
Secondary Accession Numbers
  • BMDB00164
Metabolite Identification
Common NameMethylamine
DescriptionMethylamine, also known as aminomethane or methanamine, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. Methylamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Methylamine exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydroxymandelaldehyde and methylamine can be biosynthesized from epinephrine through its interaction with the enzyme amine oxidase [flavin-containing] a. In cattle, methylamine is involved in the metabolic pathway called the tyrosine metabolism pathway. Methylamine is a potentially toxic compound.
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
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-93.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1080 mg/mL at 25 °CNot Available
LogP-0.57HANSCH,C ET AL. (1995)
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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-50fb665f1ba89a03baf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-9000000000-93f5049fa2e67d0da26dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-53c64a174764bada8913View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-1c10568342e547416eafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-2910620cfb01718df17fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-2910620cfb01718df17fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-2910620cfb01718df17fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-f140127f4f4b677d2975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-f140127f4f4b677d2975View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-f140127f4f4b677d2975View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-43b9d7b881c659f2ceb1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Milk
  • Ruminal Fluid
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified181-2390 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified4-49 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified132+/-116 uMNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Treated with growth-promoting hormones
details
HMDB IDHMDB0000164
DrugBank IDDB01828
Phenol Explorer Compound IDNot Available
FooDB IDFDB003958
KNApSAcK IDNot Available
Chemspider ID6089
KEGG Compound IDC00218
BioCyc IDMETHYLAMINE
BiGG ID1800349
Wikipedia LinkMethylamine
METLIN ID3767
PubChem Compound6329
PDB IDNot Available
ChEBI ID16830
References
Synthesis ReferenceDenham, William S.; Knapp, Lionel F. The preparation of methylamine from ammonium methyl sulfate. Journal of the Chemical Society, Transactions (1920), 117 236-47.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21398
Molecular weight:
59758.0
Reactions
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails