Methylamine
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Basic Info
| Common Name | Methylamine(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. |
| FRCD ID | F05238 |
| CAS Number | 74-89-5 |
| PubChem CID | 6329 |
| Formula | CH5N |
| IUPAC Name | methanamine |
| InChI Key | BAVYZALUXZFZLV-UHFFFAOYSA-N |
| InChI | InChI=1S/CH5N/c1-2/h2H2,1H3 |
| Canonical SMILES | CN |
| Isomeric SMILES | CN |
| Wikipedia | Methylamine |
| Synonyms |
Carbinamine
METHYLAMINE
Methanamine
Aminomethane
Monomethylamine
74-89-5
Mercurialin
N-Methylamine
Methylaminen
Metilamine
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Amines |
| Intermediate Tree Nodes | Primary amines |
| Direct Parent | Monoalkylamines |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Organopnictogen compound - Hydrocarbon derivative - Primary aliphatic amine - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 31.058 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 2 |
| Monoisotopic Mass | 31.042 |
| Exact Mass | 31.042 |
| XLogP | -0.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 2 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9394 |
| Human Intestinal Absorption | HIA+ | 0.9759 |
| Caco-2 Permeability | Caco2+ | 0.6811 |
| P-glycoprotein Substrate | Non-substrate | 0.8684 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9875 |
| Non-inhibitor | 0.9877 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8865 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.9055 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8546 |
| CYP450 2D6 Substrate | Non-substrate | 0.7879 |
| CYP450 3A4 Substrate | Non-substrate | 0.8005 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9568 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9616 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9538 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9736 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9643 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9433 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9495 |
| Non-inhibitor | 0.9672 | |
| AMES Toxicity | Non AMES toxic | 0.9444 |
| Carcinogens | Carcinogens | 0.5549 |
| Fish Toxicity | Low FHMT | 0.8893 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9375 |
| Honey Bee Toxicity | High HBT | 0.6817 |
| Biodegradation | Ready biodegradable | 0.7561 |
| Acute Oral Toxicity | II | 0.7363 |
| Carcinogenicity (Three-class) | Non-required | 0.6441 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 1.3265 | LogS |
| Caco-2 Permeability | 1.3089 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.3442 | LD50, mol/kg |
| Fish Toxicity | 3.3692 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.7143 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Supplementing phytogenic compounds or autolyzed yeast modulates ruminal biogenic amines and plasma metabolome in dry cows experiencing subacute ruminal acidosis. | J Dairy Sci | 2018 Jul 18 | 30031584 |
| The fragmentation mechanism and immune-protective effect of CfTEP in the scallop Chlamys farreri. | Dev Comp Immunol | 2017 Nov | 28625746 |
| In vitro effects of sodium bicarbonate buffer on rumen fermentation, levels of lipopolysaccharide and biogenic amine, and composition of rumen microbiota. | J Sci Food Agric | 2017 Mar | 27339112 |
| Vasoactivity and Vasoconstriction Changes in Cattle Related to Time off Toxic Endophyte-Infected Tall Fescue. | Toxins (Basel) | 2016 Sep 22 | 27669299 |
| Methylamine induced hypophagia is mediated via dopamine D1 and D2 receptors inneonatal meat chicks. | Vet Res Commun | 2016 Mar | 26685977 |
| A new room temperature gas sensor based on pigment-sensitized TiO2 thin film for amines determination. | Biosens Bioelectron | 2015 May 15 | 24934102 |
| Gender-specific effects of a phytogenic feed additive on performance, intestinal physiology and morphology in broiler chickens. | J Anim Physiol Anim Nutr (Berl) | 2015 Aug | 25073418 |
| Hepatotoxic constituents and toxicological mechanism of Xanthium strumarium L. fruits. | J Ethnopharmacol | 2014 Mar 14 | 24447814 |
| Palladium nanoparticles decorated on reduced graphene oxide rotating diskelectrodes toward ultrasensitive hydrazine detection: effects of particle sizeand hydrodynamic diffusion. | Anal Chem | 2014 Dec 16 | 25391449 |
| Melatonin is formed during winemaking at safe levels of biogenic amines. | Food Chem Toxicol | 2013 Jul | 23531627 |
| Effects of a Fusarium toxin-contaminated maize treated with sodium metabisulphite, methylamine and calcium hydroxide in diets for female piglets. | Arch Anim Nutr | 2013 Aug | 23859352 |
| 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 Res | 2013 Aug | 23536360 |
| 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 A | 2013 Apr 19 | 23489497 |
| Free amino acids and biogenic amines in Alicante Monastrell wines. | Food Chem | 2012 Dec 1 | 22953887 |
| Modifications and insights into a method for the analysis of the nitrogen mustard mechlorethamine by high-performance liquid chromatography. | Anal Chim Acta | 2008 May 26 | 18471487 |
| Mechanistic pathways of formation of acrylamide from different amino acids. | Adv Exp Med Biol | 2005 | 16438299 |
| Chemiluminescence determination of carbofuran and promecarb by flow injectionanalysis using two photochemical reactions. | Analyst | 2002 Nov | 12475046 |
| Methylamine in human urine. | Clin Chim Acta | 2001 Oct | 11580915 |
| A role for serotonin in lipopolysaccharide-induced anorexia in rats. | Pharmacol Biochem Behav | 2001 Feb | 11267641 |
| Potential cytotoxic effect of chronic administration of creatine, a nutrition supplement to augment athletic performance. | Med Hypotheses | 2000 May | 10859677 |
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
- 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
- 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
- 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 ]