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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-02-28 12:00:41 UTC |
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Update Date | 2019-01-11 19:16:18 UTC |
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HMDB ID | HMDB0001888 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N,N-Dimethylformamide |
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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. (PMID: 17254560 ). |
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Structure | |
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Synonyms | Value | Source |
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Dimethylformamide | ChEBI | DMF | ChEBI | N,N-Dimethylmethanamide | ChEBI | N-Formyldimethylamine | ChEBI | Dimethyl formamide | HMDB | Dimethyl-formamide | HMDB | Dimethylamid kyseliny mravenci | HMDB | Dimethylforamide | HMDB | Dimethylformamid | HMDB | Dimetilformamide | HMDB | Dimetylformamidu | HMDB | Dwumetyloformamid | HMDB | Formyldimethylamine | HMDB | N,N- Dimethyl formamide | HMDB | N,N- Dimethylformamide | HMDB | N,N-Dimethyl-formamide | HMDB | N,N Dimethylformamide | MeSH |
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Chemical Formula | C3H7NO |
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Average Molecular Weight | 73.0938 |
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Monoisotopic Molecular Weight | 73.052763851 |
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IUPAC Name | N,N-dimethylformamide |
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Traditional Name | dimethylformamide |
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CAS Registry Number | 68-12-2 |
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SMILES | CN(C)C=O |
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InChI Identifier | InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 |
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InChI Key | ZMXDDKWLCZADIW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as tertiary carboxylic acid amides. These are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acid derivatives |
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Direct Parent | Tertiary carboxylic acid amides |
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Alternative Parents | |
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Substituents | - Tertiary carboxylic acid amide
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Route of exposure: Biological location: |
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Role | Indirect biological role: Environmental role: Industrial application: |
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Physical Properties |
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State | Liquid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | -60.4 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000000 mg/L at 25 °C | Not Available | LogP | -1.01 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-006x-9000000000-34e0d5dce52ab7332a48 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-9000000000-2fc3e0f8da9a647359fa | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001l-9000000000-f4fe42c25bc21b32c720 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000x-9000000000-c16bd85f59063ed223cd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-9000000000-cc68a0ecc7c49de9adf0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-00di-9000000000-9f91c0e4ecf9323c5268 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9000000000-cc68a0ecc7c49de9adf0 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9000000000-9f91c0e4ecf9323c5268 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-9000000000-7021cfe3ddcd7eead969 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9000000000-ceda884adf62fcbbade6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-9000000000-dfa16f4b703eedcce213 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-9000000000-20383304fc1b3341c39d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-9000000000-4add65e7ea3604d5d1fc | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-9000000000-a05f660af113d947481e | View in MoNA |
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MS | Mass Spectrum (Electron Ionization) | splash10-006x-9000000000-039511887fde37138176 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | | Not Available | Not Available | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.17 (0.06-0.77) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 1.27 (0.18-2.24) umol/mmol creatinine | Adult (>18 years old) | Both | Smoking | | details |
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Associated Disorders and Diseases |
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Disease References | Smoking |
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- Schettgen T, Musiol A, Kraus T: Simultaneous determination of mercapturic acids derived from ethylene oxide (HEMA), propylene oxide (2-HPMA), acrolein (3-HPMA), acrylamide (AAMA) and N,N-dimethylformamide (AMCC) in human urine using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008 Sep;22(17):2629-38. doi: 10.1002/rcm.3659. [PubMed:18666198 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB01844 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB004724 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5993 |
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KEGG Compound ID | C03134 |
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BioCyc ID | CPD-581 |
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BiGG ID | Not Available |
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Wikipedia Link | Dimethylformamide |
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METLIN ID | Not Available |
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PubChem Compound | 6228 |
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PDB ID | DMF |
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ChEBI ID | 17741 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Shieh DB, Chen CC, Shih TS, Tai HM, Wei YH, Chang HY: Mitochondrial DNA alterations in blood of the humans exposed to N,N-dimethylformamide. Chem Biol Interact. 2007 Feb 20;165(3):211-9. Epub 2006 Dec 20. [PubMed:17254560 ]
- Redlich CA, Beckett WS, Sparer J, Barwick KW, Riely CA, Miller H, Sigal SL, Shalat SL, Cullen MR: Liver disease associated with occupational exposure to the solvent dimethylformamide. Ann Intern Med. 1988 May;108(5):680-6. [PubMed:3358569 ]
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