Basic Info

Common NameMethylamine(F05238)
2D Structure
Description

Methylamine 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. (A3265, A3266, A3267).

FRCD IDF05238
CAS Number74-89-5
PubChem CID6329
FormulaCH5N
IUPAC Name

methanamine

InChI Key

BAVYZALUXZFZLV-UHFFFAOYSA-N

InChI

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

Canonical SMILES

CN

Isomeric SMILES

CN

WikipediaMethylamine
Synonyms
        
            Carbinamine
        
            METHYLAMINE
        
            Methanamine
        
            Aminomethane
        
            Monomethylamine
        
            74-89-5
        
            Mercurialin
        
            N-Methylamine
        
            Methylaminen
        
            Metilamine
        
Classifies
                

                  
                    Predicted: Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassAmines
Intermediate Tree NodesPrimary amines
Direct ParentMonoalkylamines
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOrganopnictogen compound - Hydrocarbon derivative - Primary aliphatic amine - Aliphatic acyclic compound
DescriptionThis compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.

Properties

Property NameProperty Value
Molecular Weight31.058
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity2
Monoisotopic Mass31.042
Exact Mass31.042
XLogP-0.7
Formal Charge0
Heavy Atom Count2
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9394
Human Intestinal AbsorptionHIA+0.9759
Caco-2 PermeabilityCaco2+0.6811
P-glycoprotein SubstrateNon-substrate0.8684
P-glycoprotein InhibitorNon-inhibitor0.9875
Non-inhibitor0.9877
Renal Organic Cation TransporterNon-inhibitor0.8865
Distribution
Subcellular localizationLysosome0.9055
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8546
CYP450 2D6 SubstrateNon-substrate0.7879
CYP450 3A4 SubstrateNon-substrate0.8005
CYP450 1A2 InhibitorNon-inhibitor0.9568
CYP450 2C9 InhibitorNon-inhibitor0.9616
CYP450 2D6 InhibitorNon-inhibitor0.9538
CYP450 2C19 InhibitorNon-inhibitor0.9736
CYP450 3A4 InhibitorNon-inhibitor0.9643
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9433
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9495
Non-inhibitor0.9672
AMES ToxicityNon AMES toxic0.9444
CarcinogensCarcinogens 0.5549
Fish ToxicityLow FHMT0.8893
Tetrahymena Pyriformis ToxicityLow TPT0.9375
Honey Bee ToxicityHigh HBT0.6817
BiodegradationReady biodegradable0.7561
Acute Oral ToxicityII0.7363
Carcinogenicity (Three-class)Non-required0.6441

Model Value Unit
Absorption
Aqueous solubility1.3265LogS
Caco-2 Permeability1.3089LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.3442LD50, mol/kg
Fish Toxicity3.3692pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.7143pIGC50, ug/L

References

TitleJournalDatePubmed ID
Supplementing phytogenic compounds or autolyzed yeast modulates ruminal biogenic amines and plasma metabolome in dry cows experiencing subacute ruminal acidosis.J Dairy Sci2018 Jul 1830031584
The fragmentation mechanism and immune-protective effect of CfTEP in the scallop Chlamys farreri.Dev Comp Immunol2017 Nov28625746
In vitro effects of sodium bicarbonate buffer on rumen fermentation, levels of lipopolysaccharide and biogenic amine, and composition of rumen microbiota.J Sci Food Agric2017 Mar27339112
Vasoactivity and Vasoconstriction Changes in Cattle Related to Time off Toxic Endophyte-Infected Tall Fescue.Toxins (Basel)2016 Sep 2227669299
Methylamine induced hypophagia is mediated via dopamine D1 and D2 receptors inneonatal meat chicks.Vet Res Commun2016 Mar26685977
A new room temperature gas sensor based on pigment-sensitized TiO2 thin film for amines determination.Biosens Bioelectron2015 May 1524934102
Gender-specific effects of a phytogenic feed additive on performance, intestinal physiology and morphology in broiler chickens.J Anim Physiol Anim Nutr (Berl)2015 Aug25073418
Hepatotoxic constituents and toxicological mechanism of Xanthium strumarium L. fruits.J Ethnopharmacol2014 Mar 1424447814
Palladium nanoparticles decorated on reduced graphene oxide rotating diskelectrodes toward ultrasensitive hydrazine detection: effects of particle sizeand hydrodynamic diffusion.Anal Chem2014 Dec 1625391449
Melatonin is formed during winemaking at safe levels of biogenic amines.Food Chem Toxicol2013 Jul23531627
Effects of a Fusarium toxin-contaminated maize treated with sodium metabisulphite, methylamine and calcium hydroxide in diets for female piglets.Arch Anim Nutr2013 Aug23859352
Hydrothermal treatment of naturally contaminated maize in the presence of sodium metabisulfite, methylamine and calcium hydroxide; effects on the concentration of zearalenone and deoxynivalenol.Mycotoxin Res2013 Aug23536360
Amine modified graphene as reversed-dispersive solid phase extraction materialscombined with liquid chromatography-tandem mass spectrometry for pesticidemulti-residue analysis in oil crops.J Chromatogr A2013 Apr 1923489497
Free amino acids and biogenic amines in Alicante Monastrell wines.Food Chem2012 Dec 122953887
Modifications and insights into a method for the analysis of the nitrogen mustard mechlorethamine by high-performance liquid chromatography.Anal Chim Acta2008 May 2618471487
Mechanistic pathways of formation of acrylamide from different amino acids.Adv Exp Med Biol200516438299
Chemiluminescence determination of carbofuran and promecarb by flow injectionanalysis using two photochemical reactions.Analyst2002 Nov12475046
Methylamine in human urine.Clin Chim Acta2001 Oct11580915
A role for serotonin in lipopolysaccharide-induced anorexia in rats.Pharmacol Biochem Behav2001 Feb11267641
Potential cytotoxic effect of chronic administration of creatine, a nutrition supplement to augment athletic performance.Med Hypotheses2000 May10859677

Targets

General Function:
Vitamin d binding
Specific Function:
May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
Gene Name:
KL
Uniprot ID:
Q9UEF7
Molecular Weight:
116179.815 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Superoxide-generating nadph oxidase activity
Specific Function:
Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
Gene Name:
NOX4
Uniprot ID:
Q9NPH5
Molecular Weight:
66930.995 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Schulz AM, Terne C, Jankowski V, Cohen G, Schaefer M, Boehringer F, Tepel M, Kunkel D, Zidek W, Jankowski J: Modulation of NADPH oxidase activity by known uraemic retention solutes. Eur J Clin Invest. 2014 Aug;44(8):802-11. doi: 10.1111/eci.12297. [25041433 ]