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Record Information
Version3.6
Creation Date2006-02-28 12:00:41 UTC
Update Date2016-02-11 01:05:04 UTC
HMDB IDHMDB01888
Secondary Accession NumbersNone
Metabolite Identification
Common NameN,N-Dimethylformamide
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. (PMID: 17254560 ).
Structure
Thumb
Synonyms
ValueSource
N,N-DimethylmethanamideKegg
DMFKegg
Dimethyl formamideHMDB
Dimethyl-formamideHMDB
Dimethylamid kyseliny mravenciHMDB
DimethylforamideHMDB
DimethylformamidHMDB
DimethylformamideHMDB
DimetilformamideHMDB
DimetylformamiduHMDB
DwumetyloformamidHMDB
FormyldimethylamineHMDB
N,N- Dimethyl formamideHMDB
N,N- DimethylformamideHMDB
N,N-Dimethyl-formamideHMDB
N-FormyldimethylamineHMDB
Chemical FormulaC3H7NO
Average Molecular Weight73.0938
Monoisotopic Molecular Weight73.052763851
IUPAC NameN,N-dimethylformamide
Traditional Namedimethylformamide
CAS Registry Number68-12-2
SMILES
CN(C)C=O
InChI Identifier
InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3
InChI KeyInChIKey=ZMXDDKWLCZADIW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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 ≠ 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
  • Tertiary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Toxin/Pollutant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-60.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000000 mg/L at 25 °CNot Available
LogP-1.01HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility725.0 mg/mLALOGPS
logP-0.77ALOGPS
logP-0.63ChemAxon
logS1ALOGPS
pKa (Strongest Basic)-0.65ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.77 m3·mol-1ChemAxon
Polarizability7.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-006x-9000000000-039511887fde37138176View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.17 (0.06-0.77) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.27 (0.18-2.24) umol/mmol creatinineAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Smoking
  1. 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. [18666198 ]
Associated OMIM IDsNone
DrugBank IDDB01844
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB004724
KNApSAcK IDNot Available
Chemspider ID5993
KEGG Compound IDC03134
BioCyc IDCPD-581
BiGG IDNot Available
Wikipedia LinkN,N-Dimethylformamide
NuGOwiki LinkHMDB01888
Metagene LinkHMDB01888
METLIN IDNot Available
PubChem Compound6228
PDB IDDMF
ChEBI ID17741
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]

Enzymes

General function:
Involved in aspartic-type endopeptidase activity
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:
45057.1
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:
Involved in serine-type endopeptidase activity
Specific function:
Acts upon elastin
Gene Name:
CELA1
Uniprot ID:
Q9UNI1
Molecular weight:
27798.0
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 ]