Methylamine (CHEM003111)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2014-08-29 05:46:57 UTC
Update Date2026-03-26 22:53:24 UTC
Accession NumberCHEM003111
Identification
Common NameMethylamine
ClassSmall Molecule
DescriptionMethylamine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. 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 H2O2 produced in the oxidation of these amines. (2, 3, 4).
Contaminant Sources
  • Clean Air Act Chemicals
  • DEA Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • OSHA Hazardous Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Uremic Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass31.057 g/mol
Monoisotopic Mass31.042 g/mol
CAS Registry Number74-89-5
IUPAC Namemethanamine
Traditional Namemethylamine
SMILESCN
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-93.4°C
Boiling PointNot Available
Solubility1080 mg/mL at 25°C
Predicted 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
Bioavailability1ChemAxon
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
Toxicity Profile
Route of ExposureEndogenous, Ingestion, Dermal (contact)
Mechanism of ToxicityUremic toxins such as methylamine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (6). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (7)
MetabolismUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNaturally produced by the body (endogenous).
Minimum Risk LevelNot Available
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
SymptomsAs a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Concentrations
Not Available
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 Reference

Charles Pigerol, Pierre Eymard, Jean-Claude Vernieres, Jean-Pierre Werbenec, “Active derivatives of methylamine, therapeutic compositions containing the same and processes for preparing the said derivatives and compositions.” U.S. Patent US4026925, issued March, 1956.

MSDSLink
General References
1. Denham, William S.; Knapp, Lionel F. The preparation of methylamine from ammonium methyl sulfate. Journal of the Chemical Society, Transactions (1920), 117 236-47.
2. 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.
3. 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.
4. Denham, William S.; Knapp, Lionel F. The preparation of methylamine from ammonium methyl sulfate. Journal of the Chemical Society, Transactions (1920), 117 236-47.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=11580915
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=11991665
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=18312416