Dimethylamine
(right click,save link as to download,it is a temp file,please download as soon as possible, you can also use CTRL+S to save the whole html page)
Basic Info
| Common Name | Dimethylamine(F05235) |
| 2D Structure | |
| Description | Dimethylamine 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. Dimethylamine (DMA) is an organic secondary amine. It is a colorless, liquefied and flammable gas with an ammonia and fish-like odor. Dimethylamine is abundantly present in human urine. Main sources of urinary DMA have been reported to include trimethylamine N-oxide, a common food component, and asymmetric dimethylarginine (ADMA), an endogenous inhibitor of nitric oxide (NO) synthesis. ADMA is excreted in the urine in part unmetabolized and in part after hydrolysis to DMA by dimethylarginine dimethylaminohydrolase (DDAH). Statistically significant increases in urinary DMA have been found in individuals after the consumption of fish and seafoods. The highest values were obtained for individuals that consumed coley, squid and whiting with cod, haddock, sardine, skate and swordfish As a pure chemical substance Dimethylamine is used as dehairing agent in tanning, in dyes, in rubber accelerators, in soaps and cleaning compounds and as an agricultural fungicide. In the body, DMA also undergoes nitrosation under weak acid conditions to give dimethlynitrosamine. |
| FRCD ID | F05235 |
| CAS Number | 124-40-3 |
| PubChem CID | 674 |
| Formula | C2H7N |
| IUPAC Name | N-methylmethanamine |
| InChI Key | ROSDSFDQCJNGOL-UHFFFAOYSA-N |
| InChI | InChI=1S/C2H7N/c1-3-2/h3H,1-2H3 |
| Canonical SMILES | CNC |
| Isomeric SMILES | CNC |
| Wikipedia | Dimethylamine |
| Synonyms |
dimethylamine
N-Methylmethanamine
124-40-3
N,N-Dimethylamine
Methanamine, N-methyl-
Dimethylamin
dimethyl amine
dimethyl-amine
Dimethylamine anhydrous
Dimethylamine (anhydrous)
|
| Classifies |
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 | Secondary amines |
| Direct Parent | Dialkylamines |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Secondary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 45.085 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 2.8 |
| Monoisotopic Mass | 45.058 |
| Exact Mass | 45.058 |
| XLogP | -0.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 3 |
| 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+ | 0.9544 |
| Human Intestinal Absorption | HIA+ | 0.9853 |
| Caco-2 Permeability | Caco2+ | 0.6888 |
| P-glycoprotein Substrate | Non-substrate | 0.7948 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9699 |
| Non-inhibitor | 0.9871 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8814 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.8554 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8389 |
| CYP450 2D6 Substrate | Non-substrate | 0.7766 |
| CYP450 3A4 Substrate | Non-substrate | 0.6989 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9210 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9501 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9058 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9432 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9687 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9333 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9261 |
| Non-inhibitor | 0.9450 | |
| AMES Toxicity | Non AMES toxic | 0.9333 |
| Carcinogens | Carcinogens | 0.5689 |
| Fish Toxicity | Low FHMT | 0.7226 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9399 |
| Honey Bee Toxicity | High HBT | 0.6886 |
| Biodegradation | Ready biodegradable | 0.7675 |
| Acute Oral Toxicity | III | 0.8225 |
| Carcinogenicity (Three-class) | Non-required | 0.6996 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.8422 | LogS |
| Caco-2 Permeability | 1.5142 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8416 | LD50, mol/kg |
| Fish Toxicity | 2.9112 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.4353 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Development of an SPME-GC-MS method for the specific quantification ofdimethylamine and trimethylamine: use of a new ratio for the freshness monitoringof cod fillets. | J Sci Food Agric | 2016 Aug | 26676937 |
| 1H NMR-based metabolomics investigation of copper-laden rat: a model of Wilson's disease. | PLoS One | 2015 Apr 7 | 25849323 |
| Hepatotoxic constituents and toxicological mechanism of Xanthium strumarium L. fruits. | J Ethnopharmacol | 2014 Mar 14 | 24447814 |
| Metabolic influence of acute cyadox exposure on Kunming mice. | J Proteome Res | 2013 Jan 4 | 23234330 |
| Toxicokinetics and recovery studies of dicamba dimethyl amine salt in goats following single oral administration. | J Sci Food Agric | 2010 Jan 30 | 20355040 |
| Simultaneous determination of dimethylamine, trimethylamine andtrimethylamine-n-oxide in aquatic products extracts by ion chromatography withnon-suppressed conductivity detection. | J Chromatogr A | 2009 Jul 31 | 19559439 |
| Metabolic profiling reveals a contribution of gut microbiota to fatty liverphenotype in insulin-resistant mice. | Proc Natl Acad Sci U S A | 2006 Aug 15 | 16895997 |
| Additive impairment of the barrier function and irritation by biogenic amines andsodium lauryl sulphate: a controlled in vivo tandem irritation study. | Skin Pharmacol Physiol | 2005 Mar-Apr | 15767770 |
| Detection of in vivo genotoxicity of endogenously formed N-nitroso compounds and suppression by ascorbic acid, teas and fruit juices. | Mutat Res | 2003 Aug 5 | 12948815 |
| Major degradation pathway of thiuram in tap water processed by oxidation withsodium hypochlorite. | J Agric Food Chem | 1999 Jul | 10552586 |
| Potentiation of ferrous sulphate and ascorbate on the microbial transformation ofendogenous trimethylamine N-oxide to trimethylamine and dimethylamine in squidextracts. | Food Chem Toxicol | 1989 Sep | 2807105 |
| Formation of a mutagenic diazoquinone by interaction of phenol with nitrite. | Food Chem Toxicol | 1988 Mar | 3366422 |
Targets
- General Function:
- Histamine receptor activity
- Specific Function:
- The H3 subclass of histamine receptors could mediate the histamine signals in CNS and peripheral nervous system. Signals through the inhibition of adenylate cyclase and displays high constitutive activity (spontaneous activity in the absence of agonist). Agonist stimulation of isoform 3 neither modified adenylate cyclase activity nor induced intracellular calcium mobilization.
- Gene Name:
- HRH3
- Uniprot ID:
- Q9Y5N1
- Molecular Weight:
- 48670.81 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 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:
- 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
- Mechanism of Action:
- Klotho acts as a humoral factor to reduce H2O2-induced apoptosis and cellular senescence in vascular cells. Klotho 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. Dimethylamine can combine with tyrosine and a sulfur ingredient such as lipoic acid or glutathione.
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
- Mechanism of Action:
- Klotho expression and production were suppressed in SHRs, which were reverted by AAV.mKL. AAV.mKL increased plasma interleukin 10 levels but decreased Nox2 expression, NADPH oxidase activity, and superoxide production in kidneys and aortas in SHRs.
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 ]