Hmdb loader
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
  • HMDB0002983
  • HMDB00164
  • HMDB0060291
  • HMDB02983
  • HMDB60291
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
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
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
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
PropertyValueSource
Water Solubility367 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+113.09530932474
DeepCCS[M-H]-111.19930932474
DeepCCS[M-2H]-146.38330932474
DeepCCS[M+Na]+120.61730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethylamineCN1027.7Standard polar33892256
MethylamineCN322.7Standard non polar33892256
MethylamineCN392.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methylamine,1TMS,isomer #1CN[Si](C)(C)C623.3Semi standard non polar33892256
Methylamine,1TMS,isomer #1CN[Si](C)(C)C658.5Standard non polar33892256
Methylamine,1TMS,isomer #1CN[Si](C)(C)C715.5Standard polar33892256
Methylamine,2TMS,isomer #1CN([Si](C)(C)C)[Si](C)(C)C866.2Semi standard non polar33892256
Methylamine,2TMS,isomer #1CN([Si](C)(C)C)[Si](C)(C)C851.8Standard non polar33892256
Methylamine,2TMS,isomer #1CN([Si](C)(C)C)[Si](C)(C)C822.0Standard polar33892256
Methylamine,1TBDMS,isomer #1CN[Si](C)(C)C(C)(C)C865.9Semi standard non polar33892256
Methylamine,1TBDMS,isomer #1CN[Si](C)(C)C(C)(C)C834.7Standard non polar33892256
Methylamine,1TBDMS,isomer #1CN[Si](C)(C)C(C)(C)C896.0Standard polar33892256
Methylamine,2TBDMS,isomer #1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1258.3Semi standard non polar33892256
Methylamine,2TBDMS,isomer #1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1258.0Standard non polar33892256
Methylamine,2TBDMS,isomer #1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1106.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methylamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-50fb665f1ba89a03baf92017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methylamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-43b9d7b881c659f2ceb12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylamine Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-9000000000-93f5049fa2e67d0da26d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylamine Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-53c64a174764bada89132012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methylamine Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-9000000000-1c10568342e547416eaf2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 10V, Positive-QTOFsplash10-001i-9000000000-2910620cfb01718df17f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 20V, Positive-QTOFsplash10-001i-9000000000-2910620cfb01718df17f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 40V, Positive-QTOFsplash10-001i-9000000000-2910620cfb01718df17f2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 10V, Negative-QTOFsplash10-001i-9000000000-f140127f4f4b677d29752017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 20V, Negative-QTOFsplash10-001i-9000000000-f140127f4f4b677d29752017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 40V, Negative-QTOFsplash10-001i-9000000000-f140127f4f4b677d29752017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 10V, Negative-QTOFsplash10-001i-9000000000-986b844d44ea8cab88772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 20V, Negative-QTOFsplash10-001i-9000000000-986b844d44ea8cab88772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 40V, Negative-QTOFsplash10-001i-9000000000-986b844d44ea8cab88772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 10V, Positive-QTOFsplash10-001i-9000000000-d90d418cf76ae365e6c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 20V, Positive-QTOFsplash10-001i-9000000000-d90d418cf76ae365e6c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methylamine 40V, Positive-QTOFsplash10-001i-9000000000-d90d418cf76ae365e6c52021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1.0 (0.37-4.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedBoth
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified258 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified196 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified178 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
SalivaDetected and Quantified25.55 +/- 13.26 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified158 (0.00-316) uMAdult (>18 years old)BothNormal details
SweatDetected and Quantified< 10 uMAdult (60 years old)Male
Normal
details
SweatDetected and Quantified< 10 uMAdult (40 years old)Male
Normal
details
UrineDetected and Quantified5.906 +/- 3.776 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected and Quantified1.46 +/- 0.13 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified13.6 +/- 3.1 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.0 (1.5-11.9) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified10.5 (9.8-12.5) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified18.68 +/- 3.22 uMAdult (>18 years old)Bothuremia details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedasymptomatic diverticulosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specifiedsymptomatic uncomplicated diverticular disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohn's disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn’s Disease
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
UrineDetected and Quantified8.09 +/- 6.297 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
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
  1. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. [PubMed:7762816 ]
  2. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
  3. Wolfe CL, Warrington JA, Davis S, Green S, Norcum MT: Isolation and characterization of human nuclear and cytosolic multisynthetase complexes and the intracellular distribution of p43/EMAPII. Protein Sci. 2003 Oct;12(10):2282-90. [PubMed:14500886 ]
  4. Wolkers WF, Looper SA, Fontanilla RA, Tsvetkova NM, Tablin F, Crowe JH: Temperature dependence of fluid phase endocytosis coincides with membrane properties of pig platelets. Biochim Biophys Acta. 2003 Jun 10;1612(2):154-63. [PubMed:12787933 ]
  5. Stanic P, Tandara M, Sonicki Z, Simunic V, Radakovic B, Suchanek E: Comparison of protective media and freezing techniques for cryopreservation of human semen. Eur J Obstet Gynecol Reprod Biol. 2000 Jul;91(1):65-70. [PubMed:10817881 ]
  6. Zeisel SH, Gettner S, Youssef M: Formation of aliphatic amine precursors of N-nitrosodimethylamine after oral administration of choline and choline analogues in the rat. Food Chem Toxicol. 1989 Jan;27(1):31-4. [PubMed:2703191 ]
  7. O'Sullivan J, Unzeta M, Healy J, O'Sullivan MI, Davey G, Tipton KF: Semicarbazide-sensitive amine oxidases: enzymes with quite a lot to do. Neurotoxicology. 2004 Jan;25(1-2):303-15. [PubMed:14697905 ]
  8. Sawetawan C, Bruns ES, Prins GS: Improvement of post-thaw sperm motility in poor quality human semen. Fertil Steril. 1993 Oct;60(4):706-10. [PubMed:8405530 ]
  9. Gunnarsson M, Sundstrom P, Stigbrand T, Jensen PE: Native and transformed alpha2-macroglobulin in plasma from patients with multiple sclerosis. Acta Neurol Scand. 2003 Jul;108(1):16-21. [PubMed:12807388 ]
  10. Kokubo T, Kushitani H, Sakka S, Kitsugi T, Yamamuro T: Solutions able to reproduce in vivo surface-structure changes in bioactive glass-ceramic A-W. J Biomed Mater Res. 1990 Jun;24(6):721-34. [PubMed:2361964 ]
  11. Mashige F, Imai K, Osuga T: A simple and sensitive assay of total serum bile acids. Clin Chim Acta. 1976 Jul 1;70(1):79-86. [PubMed:947625 ]
  12. Wosikowski K, Biedermann E, Rattel B, Breiter N, Jank P, Loser R, Jansen G, Peters GJ: In vitro and in vivo antitumor activity of methotrexate conjugated to human serum albumin in human cancer cells. Clin Cancer Res. 2003 May;9(5):1917-26. [PubMed:12738750 ]
  13. Tencer J, Thysell H, Andersson K, Grubb A: Long-term stability of albumin, protein HC, immunoglobulin G, kappa- and lambda-chain-immunoreactivity, orosomucoid and alpha 1-antitrypsin in urine stored at -20 degrees C. Scand J Urol Nephrol. 1997 Feb;31(1):67-71. [PubMed:9060087 ]
  14. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  15. 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. [PubMed:16049393 ]
  16. 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. [PubMed:12686132 ]
  17. 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. [PubMed:17406961 ]
  18. 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 ]

Enzymes

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
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
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
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
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