Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:22 UTC
Update Date2014-12-24 20:21:25 UTC
Accession NumberT3D0252
Identification
Common NameN,N-Dimethylformamide
ClassSmall Molecule
DescriptionN,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. (2).
Compound Type
  • Amide
  • Amine
  • Food Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Pollutant
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Dimethyl formamide
Dimethyl-Formamide
Dimethylforamide
Dimethylformamide
Formyldimethylamine
N,N- Dimethyl formamide
N,N- Dimethylformamide
N,N-Dimethyl-Formamide
N-Formyldimethylamine
Chemical FormulaC3H7NO
Average Molecular Mass73.094 g/mol
Monoisotopic Mass73.053 g/mol
CAS Registry Number1968-12-02
IUPAC NameN,N-dimethylformamide
Traditional Namedimethylformamide
SMILESCN(C)C=O
InChI IdentifierInChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
InChI KeyInChIKey=ZMXDDKWLCZADIW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tertiary carboxylic acid amides. Tertiary carboxylic acid amides are compounds containing an amide derivative of carboxylic acid, with the general structure RN(R1)C(R2)=O (R1-R2 any atom but H).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentTertiary carboxylic acid amides
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-60.4°C
Boiling Point153°C (307.4°F)
Solubility1000 mg/mL at 25°C
LogP-1.01
Predicted Properties
PropertyValueSource
Water Solubility725 g/LALOGPS
logP-0.77ALOGPS
logP-0.63ChemAxon
logS1ALOGPS
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.77 m³·mol⁻¹ChemAxon
Polarizability7.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-34e0d5dce52ab7332a48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9000000000-2fc3e0f8da9a647359faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001l-9000000000-f4fe42c25bc21b32c720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000x-9000000000-c16bd85f59063ed223cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-00di-9000000000-cc68a0ecc7c49de9adf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-00di-9000000000-9f91c0e4ecf9323c5268View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-9000000000-cc68a0ecc7c49de9adf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-9000000000-9f91c0e4ecf9323c5268View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-7021cfe3ddcd7eead969View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-ceda884adf62fcbbade6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-dfa16f4b703eedcce213View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-20383304fc1b3341c39dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-4add65e7ea3604d5d1fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-a05f660af113d947481eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-006x-9000000000-039511887fde37138176View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral ; inhalation ; dermal
Mechanism of ToxicityWhile the mechanism of action of dimethyl formamide has not bee fully elucidated, thiocarbamate pesticides have been shown to inhibit aldehyde dehydrogenases. (1)
MetabolismDimethyl 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.
Toxicity ValuesLD50: 2800 mg/kg (Oral, Rat) (4) LD50: 1400 mg/kg (Intraperitoneal, Rat) (4) LD50: 3800 mg/kg (Subcutaneous, Rat) (4) LD50: 2000 mg/kg (Intravenous, Rat) (4)
Lethal Dose10 grams for an adult human. (5)
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (6)
Uses/SourcesDimethyl formamide (DMF) is commonly used as a solvent for chemical reactions. (7)
Minimum Risk LevelNot Available
Health EffectsDimethyl formamide is a known hepatatotoxin. It may also cause birth defects, kidney damage, and temporary alcohol intolerance. (7)
SymptomsSymptoms of dimethyl formamide exposure may include abdominal pain, nausea, vomiting, dizziness, fatigue, headache, loss of appetite, and temporary alcohol intolerance. (7)
TreatmentAs there is no antidote for dimethyl formamide poisoning, treatment is mainly supportive and symptomatic. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01844
HMDB IDHMDB01888
PubChem Compound ID6228
ChEMBL IDNot Available
ChemSpider ID5993
KEGG IDC03134
UniProt IDNot Available
OMIM ID
ChEBI ID17741
BioCyc IDCPD-581
CTD IDNot Available
Stitch IDDimethyl formamide
PDB IDDMF
ACToR ID523
Wikipedia LinkDimethylformamide
References
Synthesis Reference

Masao Saito, Kinichi Mizuno, Yuzi Onda, Tetsuo Aoyama, Kumiko Kato, “Process for producing dimethylformamide.” U.S. Patent US4218398, issued August, 1933.

MSDSLink
General References
  1. Hart BW, Faiman MD: Inhibition of rat liver low Km aldehyde dehydrogenase by thiocarbamate herbicides. Occupational implications. Biochem Pharmacol. 1995 Jan 18;49(2):157-63. [7840792 ]
  2. 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. [17254560 ]
  3. 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. [3358569 ]
  4. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  5. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  6. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  7. Wikipedia. Dimethylformamide. Last Updated 12 June 2009. [Link]
  8. International Programme on Chemical Safety (IPCS) INCHEM (1998). Environmental Health Criteria for Dimethylformamide. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
Serine-type endopeptidase activity
Specific Function:
Acts upon elastin.
Gene Name:
CELA1
Uniprot ID:
Q9UNI1
Molecular Weight:
27797.995 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General Function:
Receptor binding
Specific Function:
Renin is a highly specific endopeptidase, whose only known function is to generate angiotensin I from angiotensinogen in the plasma, initiating a cascade of reactions that produce an elevation of blood pressure and increased sodium retention by the kidney.
Gene Name:
REN
Uniprot ID:
P00797
Molecular Weight:
45057.125 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General Function:
Electron carrier activity
Specific Function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular Weight:
56380.93 Da
References
  1. Hart BW, Faiman MD: Inhibition of rat liver low Km aldehyde dehydrogenase by thiocarbamate herbicides. Occupational implications. Biochem Pharmacol. 1995 Jan 18;49(2):157-63. [7840792 ]
General Function:
Zinc ion binding
Specific Function:
Transcriptional regulator which is important for the differentiation and maintenance of meso-diencephalic dopaminergic (mdDA) neurons during development. It is crucial for expression of a set of genes such as SLC6A3, SLC18A2, TH and DRD2 which are essential for development of mdDA neurons (By similarity).
Gene Name:
NR4A2
Uniprot ID:
P43354
Molecular Weight:
66590.375 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.63 uMATG_NURR1_TRANSAttagene
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]