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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-28 12:00:41 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001888
Secondary Accession Numbers
  • HMDB01888
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
Data?1582752214
Synonyms
ValueSource
DimethylformamideChEBI
DMFChEBI
N,N-DimethylmethanamideChEBI
N-FormyldimethylamineChEBI
Dimethyl formamideHMDB
Dimethyl-formamideHMDB
Dimethylamid kyseliny mravenciHMDB
DimethylforamideHMDB
DimethylformamidHMDB
DimetilformamideHMDB
DimetylformamiduHMDB
DwumetyloformamidHMDB
FormyldimethylamineHMDB
N,N- Dimethyl formamideHMDB
N,N- DimethylformamideHMDB
N,N-Dimethyl-formamideHMDB
N,N DimethylformamideHMDB
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 KeyZMXDDKWLCZADIW-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
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular 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)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.17231661259
DarkChem[M-H]-105.2531661259
AllCCS[M+H]+123.23932859911
AllCCS[M-H]-129.69832859911
DeepCCS[M+H]+119.49230932474
DeepCCS[M-H]-117.59630932474
DeepCCS[M-2H]-152.94330932474
DeepCCS[M+Na]+127.3530932474
AllCCS[M+H]+123.232859911
AllCCS[M+H-H2O]+118.932859911
AllCCS[M+NH4]+127.332859911
AllCCS[M+Na]+128.532859911
AllCCS[M-H]-129.732859911
AllCCS[M+Na-2H]-135.532859911
AllCCS[M+HCOO]-141.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N,N-DimethylformamideCN(C)C=O1257.7Standard polar33892256
N,N-DimethylformamideCN(C)C=O697.1Standard non polar33892256
N,N-DimethylformamideCN(C)C=O764.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N,N-Dimethylformamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-34e0d5dce52ab7332a482016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,N-Dimethylformamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-006x-9000000000-039511887fde371381762014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-00di-9000000000-2fc3e0f8da9a647359fa2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001l-9000000000-f4fe42c25bc21b32c7202012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-000x-9000000000-c16bd85f59063ed223cd2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-00di-9000000000-cc68a0ecc7c49de9adf02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-00di-9000000000-9f91c0e4ecf9323c52682012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide LC-ESI-QTOF , positive-QTOFsplash10-00di-9000000000-cc68a0ecc7c49de9adf02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide LC-ESI-QTOF , positive-QTOFsplash10-00di-9000000000-9f91c0e4ecf9323c52682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide 35V, Positive-QTOFsplash10-006y-9000000000-5543ffa660a73e2f60ae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N,N-Dimethylformamide 30V, Positive-QTOFsplash10-00di-9000000000-9f91c0e4ecf9323c52682021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 10V, Positive-QTOFsplash10-00di-9000000000-7021cfe3ddcd7eead9692016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 20V, Positive-QTOFsplash10-00di-9000000000-ceda884adf62fcbbade62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 40V, Positive-QTOFsplash10-00di-9000000000-dfa16f4b703eedcce2132016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 10V, Negative-QTOFsplash10-00di-9000000000-20383304fc1b3341c39d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 20V, Negative-QTOFsplash10-00di-9000000000-4add65e7ea3604d5d1fc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 40V, Negative-QTOFsplash10-05fr-9000000000-a05f660af113d947481e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 10V, Negative-QTOFsplash10-00di-9000000000-bc974757d0839ce6b57c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 20V, Negative-QTOFsplash10-00di-9000000000-bc974757d0839ce6b57c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 40V, Negative-QTOFsplash10-0006-9000000000-33646a67bc59fe05be542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 10V, Positive-QTOFsplash10-00di-9000000000-ca67ae001025b0816d1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 20V, Positive-QTOFsplash10-00dm-9000000000-c1637e5f95671002e1bc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N-Dimethylformamide 40V, Positive-QTOFsplash10-00di-9000000000-78ef7927403f69155f402021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.17 (0.06-0.77) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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. doi: 10.1002/rcm.3659. [PubMed:18666198 ]
Associated OMIM IDsNone
DrugBank IDDB01844
Phenol Explorer Compound IDNot Available
FooDB IDFDB004724
KNApSAcK IDNot Available
Chemspider ID5993
KEGG Compound IDC03134
BioCyc IDCPD-581
BiGG IDNot Available
Wikipedia LinkDimethylformamide
METLIN IDNot Available
PubChem Compound6228
PDB IDNot Available
ChEBI ID17741
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000352
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10592235 ]