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Showing metabocard for Methylamine (HMDB0000164)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:35 UTC
HMDB IDHMDB0000164
Secondary Accession Numbers
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 hydrogen peroxide produced in the oxidation of these amines (PMID: 16049393 , 12686132 , 17406961 ). Methylamine has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ).
Structure
Data?1676999675
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000164 (Methylamine)

  Mrv1652303202018592D          

  2  1  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
M  END
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3D MOL for HMDB0000164 (Methylamine)

HMDB0000164
     RDKit          3D
Methylamine
  7  6  0  0  0  0  0  0  0  0999 V2000
   -0.5775   -0.0536    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479   -0.0257   -0.1864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8937   -0.0387    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    0.8967   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -0.9043   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704    0.9100   -0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -0.7844    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
  2  7  1  0
M  END
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3D SDF for HMDB0000164 (Methylamine)

  Mrv1652303202018592D          

  2  1  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000164

> <DATABASE_NAME>
hmdb

> <SMILES>
CN

> <INCHI_IDENTIFIER>
InChI=1S/CH5N/c1-2/h2H2,1H3

> <INCHI_KEY>
BAVYZALUXZFZLV-UHFFFAOYSA-N

> <FORMULA>
CH5N

> <MOLECULAR_WEIGHT>
31.0571

> <EXACT_MASS>
31.042199165

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
3.8562949268232196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methanamine

> <ALOGPS_LOGP>
-1.06

> <JCHEM_LOGP>
-0.6254588653333333

> <ALOGPS_LOGS>
1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.08103885499396

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
9.918800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0000164 (Methylamine)

HMDB0000164
     RDKit          3D
Methylamine
  7  6  0  0  0  0  0  0  0  0999 V2000
   -0.5775   -0.0536    0.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8479   -0.0257   -0.1864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8937   -0.0387    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    0.8967   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -0.9043   -0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2704    0.9100   -0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656   -0.7844    0.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  1  5  1  0
  2  6  1  0
  2  7  1  0
M  END
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PDB for HMDB0000164 (Methylamine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1                                                            
MASTER        0    0    0    0    0    0    0    0    2    0    2    0
END
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3D PDB for HMDB0000164 (Methylamine)

COMPND    HMDB0000164
HETATM    1  C1  UNL     1      -0.578  -0.054   0.003  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.848  -0.026  -0.186  1.00  0.00           N  
HETATM    3  H1  UNL     1      -0.894  -0.039   1.055  1.00  0.00           H  
HETATM    4  H2  UNL     1      -0.957   0.897  -0.470  1.00  0.00           H  
HETATM    5  H3  UNL     1      -1.056  -0.904  -0.502  1.00  0.00           H  
HETATM    6  H4  UNL     1       1.270   0.910  -0.152  1.00  0.00           H  
HETATM    7  H5  UNL     1       1.366  -0.784   0.252  1.00  0.00           H  
CONECT    1    2    3    4    5
CONECT    2    6    7
END
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SMILES for HMDB0000164 (Methylamine)

CN
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INCHI for HMDB0000164 (Methylamine)

InChI=1S/CH5N/c1-2/h2H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationEnvironmental roleBiological role
Physical Properties
StateLiquid
Experimental Molecular 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)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Crohn's disease
  1. Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
  2. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Ulcerative colitis
  1. Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
  2. Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Diverticular disease
  1. Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
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
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
Food Biomarker OntologyNot Available
VMH IDMMA
MarkerDB IDMDB00000080
Good Scents IDNot Available
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)Download (PDF)
General References

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
General function:
Involved in oxidoreductase activity
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. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxidedetails
Enzyme Details
2. Amine oxidase [flavin-containing] A
General function:
Involved in oxidoreductase activity
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:
P21397
Molecular weight:
59681.27
Reactions
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
Metanephrine + Water + Oxygen → 3-Methoxy-4-hydroxyphenylglycolaldehyde + Hydrogen peroxide + Methylaminedetails
N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxidedetails
Enzyme Details
3. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
Methylamine + Oxygen + Water → Formaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
4. Retina-specific copper amine oxidase
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Methylamine + Oxygen + Water → Formaldehyde + Ammonia + Hydrogen peroxidedetails
Enzyme Details
5. Glycine dehydrogenase [decarboxylating], mitochondrial
General function:
Involved in lyase activity
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The P protein binds the alpha-amino group of glycine through its pyridoxal phosphate cofactor; CO(2) is released and the remaining methylamine moiety is then transferred to the lipoamide cofactor of the H protein.
Gene Name:
GLDC
Uniprot ID:
P23378
Molecular weight:
112728.805