N,N-Dimethylformamide
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Basic Info
| Common Name | N,N-Dimethylformamide(F03459) |
| 2D Structure | |
| 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). |
| FRCD ID | F03459 |
| CAS Number | 1968-12-02 |
| PubChem CID | 6228 |
| Formula | C3H7NO |
| IUPAC Name | N,N-dimethylformamide |
| InChI Key | ZMXDDKWLCZADIW-UHFFFAOYSA-N |
| InChI | InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3 |
| Canonical SMILES | CN(C)C=O |
| Isomeric SMILES | CN(C)C=O |
| Wikipedia | N,N-Dimethylformamide |
| Synonyms |
N-Formyldimethylamine
N,N-DIMETHYLFORMAMIDE
Dimethylformamide
68-12-2
N,N-Dimethylmethanamide
Dimethyl formamide
Formamide, N,N-dimethyl-
Dimethylformamid
DMF
Dimetilformamide
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Carboxylic acid derivatives |
| Intermediate Tree Nodes | Carboxylic acid amides |
| Direct Parent | Tertiary carboxylic acid amides |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| 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). |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 73.095 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 0 |
| Complexity | 33.9 |
| Monoisotopic Mass | 73.053 |
| Exact Mass | 73.053 |
| XLogP | -1 |
| Formal Charge | 0 |
| Heavy Atom Count | 5 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9899 |
| Human Intestinal Absorption | HIA+ | 0.9673 |
| Caco-2 Permeability | Caco2+ | 0.6997 |
| P-glycoprotein Substrate | Non-substrate | 0.8365 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9740 |
| Non-inhibitor | 0.9886 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8896 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5690 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8113 |
| CYP450 2D6 Substrate | Non-substrate | 0.8469 |
| CYP450 3A4 Substrate | Non-substrate | 0.5749 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8893 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9489 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9749 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9693 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9814 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9399 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9716 |
| Non-inhibitor | 0.9463 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Carcinogens | 0.6893 |
| Fish Toxicity | Low FHMT | 0.9031 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9819 |
| Honey Bee Toxicity | High HBT | 0.5390 |
| Biodegradation | Not ready biodegradable | 0.6188 |
| Acute Oral Toxicity | III | 0.7816 |
| Carcinogenicity (Three-class) | Non-required | 0.7336 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 1.8319 | LogS |
| Caco-2 Permeability | 1.5242 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.4483 | LD50, mol/kg |
| Fish Toxicity | 2.5789 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -1.3855 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Patulin removal from apple juice using a novel cysteine-functionalized metal-organic framework adsorbent. | Food Chem | 2019 Jan 1 | 30174021 |
| Effect of antibiotic, probiotic, and human rotavirus infection on colonisationdynamics of defined commensal microbiota in a gnotobiotic pig model. | Benef Microbes | 2018 Jan 29 | 29022385 |
| Dimethyl fumarate potentiates oncolytic virotherapy through NF-κB inhibition. | Sci Transl Med | 2018 Jan 24 | 29367345 |
| Aptamer-based polyhedral oligomeric silsesquioxane (POSS)-containing hybrid affinity monolith prepared via a "one-pot" process for selective extraction of ochratoxin A. | J Chromatogr A | 2018 Aug 17 | 29866505 |
| Inhibitory effects of Kaempferia parviflora extract on monocyte adhesion and cellular reactive oxygen species production in human umbilical vein endothelial cells. | Eur J Nutr | 2017 Apr | 26704713 |
| Chitosan grafted monomethyl fumaric acid as a potential food preservative. | Carbohydr Polym | 2016 Nov 5 | 27516253 |
| Screening of pesticide residues in honeybee wax comb by LC-ESI-MS/MS. A pilotstudy. | Chemosphere | 2016 Nov | 27522180 |
| Construction of an Electrochemical Sensor Based on Carbon Nanotubes/GoldNanoparticles for Trace Determination of Amoxicillin in Bovine Milk. | Sensors (Basel) | 2016 Jan 20 | 26805829 |
| Organic Radical-Assisted Electrochemical Exfoliation for the Scalable Production of High-Quality Graphene. | J Am Chem Soc | 2015 Nov 4 | 26460583 |
| THE COMBINED USE OF HONEY, GARLIC (ALLIUM SATIVUM L.) AND SKIMMED MILK AS ANEXTENDER FOR CHILLING SHEEP SEMEN. | Cryo Letters | 2015 Jul-Aug | 26575999 |
| Analysis of "Amitraz (sum)" in pears with incurred residues - Comparison of theapproach covering the individual metabolites via LC-MS/MS with the approachinvolving cleavage to 2,4-dimethylaniline. | Food Chem | 2015 Jan 1 | 25053051 |
| Sensitive voltammetric determination of vanillin with an AuPdnanoparticles-graphene composite modified electrode. | Food Chem | 2014 May 15 | 24423501 |
| Spectroscopic and biological approach in the characterization of a novel14-membered [N4] macrocyclic ligand and its palladium(II), platinum(II),ruthenium(III) and iridium(III) complexes. | Spectrochim Acta A Mol Biomol Spectrosc | 2014 Jan 24 | 24051297 |
| Relationship between daily habits, Streptococcus mutans, and caries amongschoolboys. | J Dent | 2013 Nov | 23948392 |
| Chemically engineered sulfated glucans from rice bran exert strong antiviralactivity at the stage of viral entry. | J Nat Prod | 2013 Dec 27 | 24279818 |
| Characterization and solvent engineering of wheat β-amylase for enhancing itsactivity and stability. | Enzyme Microb Technol | 2012 Oct 10 | 22975120 |
| Purification and characterization of a highly selective sucrose isomerase fromErwinia rhapontici NX-5. | Bioprocess Biosyst Eng | 2011 Jun | 21229265 |
| Dental caries and dental care level (restorative index) in children with diabetesmellitus type 1. | Int J Paediatr Dent | 2011 Jan | 20731732 |
| Oral health knowledge, practice, oral hygiene status, and dental cariesprevalence among visually impaired children in Bangalore. | J Indian Soc Pedod Prev Dent | 2011 Apr-Jun | 21911946 |
| Using zero inflated models to analyze dental caries with many zeroes. | Indian J Dent Res | 2010 Oct-Dec | 21187609 |
Targets
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Electron carrier activity
- Gene Name:
- ALDH2
- Uniprot ID:
- P05091
- Molecular Weight:
- 56380.93 Da
- Mechanism of Action:
- While the mechanism of action of dimethyl formamide has not bee fully elucidated, thiocarbamate pesticides have been shown to inhibit aldehyde dehydrogenases.
References
- 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
References
- 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 ]