<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4202</id>
  <title>T3D4148</title>
  <common-name>Dimethylamine</common-name>
  <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.</description>
  <cas>124-40-3</cas>
  <pubchem-id>674</pubchem-id>
  <chemical-formula>C2H7N</chemical-formula>
  <weight>45.08</weight>
  <appearance nil="true"/>
  <melting-point>-92.2°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>1630 mg/mL at 40°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Endogenous, Ingestion, Dermal (contact)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Uremic toxins such as dimethylamine 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) (A7868). 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 (A7869)</mechanism-of-toxicity>
  <metabolism>Uremic 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.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Naturally produced by the body (endogenous).</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.</health-effects>
  <symptoms>As 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.</symptoms>
  <treatment>Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.</treatment>
  <created-at type="dateTime">2014-08-29T05:46:40Z</created-at>
  <updated-at type="dateTime">2026-04-16T22:35:49Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Dimethylamine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00543</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>17170</chebi-id>
  <biocyc-id>DIMETHYLAMINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id>DMN</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CNC</moldb-smiles>
  <moldb-formula>C2H7N</moldb-formula>
  <moldb-inchi>InChI=1S/C2H7N/c1-3-2/h3H,1-2H3</moldb-inchi>
  <moldb-inchikey>ROSDSFDQCJNGOL-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">45.0837</moldb-average-mass>
  <moldb-mono-mass type="decimal">45.057849229</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Liquid</state>
  <logp>-0.38</logp>
  <hmdb-id>HMDB00087</hmdb-id>
  <chembl-id>CHEMBL120433</chembl-id>
  <chemspider-id>654</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>Zones, Stacey I.; Burton, Allen W.  Production of methylamine and dimethylamine using STI zeolite catalysts. U.S. Pat. Appl. Publ.  (2007),  6pp. </synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003108</chemdb-id>
  <dsstox-id>DTXSID5024057</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00001615</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>12.03</moldb-polar-surface-area>
  <moldb-refractivity>14.6934</moldb-refractivity>
  <moldb-polarizability>5.7548177246013354</moldb-polarizability>
  <moldb-rotatable-bond-count>0</moldb-rotatable-bond-count>
  <moldb-acceptor-count>1</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic nil="true"/>
  <moldb-pka-strongest-basic>10.522579829086101</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-0.53</moldb-alogps-logp>
  <moldb-alogps-logs>1.06</moldb-alogps-logs>
  <moldb-alogps-solubility>5.16e+02 g/l</moldb-alogps-solubility>
</compound>
