<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">253</id>
  <title>T3D0252</title>
  <common-name>N,N-Dimethylformamide</common-name>
  <description>N,N-Dimethylformamide (DMF) is a clear liquid that has been widely used in industries as a solvent, an additive, or an intermediate because of its extensive miscibility with water and most common organic solvents. Its health effects include hepatotoxicity and male reproductoxicity, possibly linked with mitochondrial DNA (mtDNA) alterations including mtDNA common deletion (delta-mtDNA4977) and mtDNA copy number; during the biotransformation of DMF in the body, free radicals are formed, including hydroxyl radicals. The world-wide consumption of DMF in 2001 was approximately 285,000 metric tonnes and most of that was used as an industrial solvent. Overexposure to DMF could result in hepatotoxicity, alcohol intolerance, possible embryotoxicity and teratogenicity in humans and animals, and decline of human sperm motility. Based on its wide application and a wide range of toxic effects, DMF has been selected as one of the four priority compounds for human field studies by the National Toxicology Program (NTP) of the US National Institute of Environmental Health Sciences (NIEHS). The current permissible exposure limit for DMF in the working environment is 10 ppm in both USA and Taiwan. The concentrations of two major DMF metabolites in urine, N-methylformamide (U-NMF) of 15 mg/L and N-acetyl-S-(N-methylcarbamoyl) cysteine (U-AMCC) of 40 mg/L, were recommended as the biological exposure indices (BEIs) by the American Conference of Governmental Industrial Hygienists for DMF exposure in workplace. (A7735).</description>
  <cas>1968-12-02</cas>
  <pubchem-id>6228</pubchem-id>
  <chemical-formula>C3H7NO</chemical-formula>
  <weight>73.052760</weight>
  <appearance nil="true"/>
  <melting-point>-60.4°C</melting-point>
  <boiling-point>153°C (307.4°F)</boiling-point>
  <density nil="true"/>
  <solubility>1000 mg/mL at 25°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral  ; inhalation  ; dermal </route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>While the mechanism of action of dimethyl formamide has not bee fully elucidated, thiocarbamate pesticides have been shown to inhibit aldehyde dehydrogenases. (A2459)</mechanism-of-toxicity>
  <metabolism>Dimethyl formamide may be absorbed following ingestion, inhalation, and dermal exposure, and is distributed evenly throughout the body. Metabolism takes place in the liver via microsomal enzyme systems, producing N-hydroxymethyl- N-methylformamide (DMF-OH) as the main urinary metabolite. </metabolism>
  <toxicity>LD50: 2800 mg/kg (Oral, Rat) (T14)
LD50: 1400 mg/kg (Intraperitoneal, Rat) (T14)
LD50: 3800 mg/kg (Subcutaneous, Rat) (T14)
LD50: 2000 mg/kg (Intravenous, Rat) (T14)</toxicity>
  <lethaldose>10 grams for an adult human. (T36)</lethaldose>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>Dimethyl formamide (DMF) is commonly used as a solvent for chemical reactions. (L1658)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Dimethyl formamide is a known hepatatotoxin. It may also cause birth defects, kidney damage, and temporary alcohol intolerance. (L1658)</health-effects>
  <symptoms>Symptoms of dimethyl formamide exposure may include abdominal pain, nausea, vomiting, dizziness, fatigue, headache, loss of appetite, and temporary alcohol intolerance. (L1658)</symptoms>
  <treatment>As there is no antidote for dimethyl formamide poisoning, treatment is mainly supportive and symptomatic. (T36)</treatment>
  <created-at type="dateTime">2009-03-06T18:58:22Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:21:25Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Dimethylformamide</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C03134</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>17741</chebi-id>
  <biocyc-id>CPD-581</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Dimethyl formamide</stitch-id>
  <drugbank-id>DB01844</drugbank-id>
  <pdb-id>DMF</pdb-id>
  <actor-id>523</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN(C)C=O</moldb-smiles>
  <moldb-formula>C3H7NO</moldb-formula>
  <moldb-inchi>InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3</moldb-inchi>
  <moldb-inchikey>InChIKey=ZMXDDKWLCZADIW-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">73.0938</moldb-average-mass>
  <moldb-mono-mass type="decimal">73.052763851</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp>-1.01</logp>
  <hmdb-id>HMDB01888</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>5993</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>&lt;p&gt;Masao Saito, Kinichi Mizuno, Yuzi Onda, Tetsuo Aoyama, Kumiko Kato, &amp;#8220;Process for producing dimethylformamide.&amp;#8221; U.S. Patent US4218398, issued August, 1933.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
