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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:23:28 UTC |
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HMDB ID | HMDB0001536 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Formamide |
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Description | Formamide, also known as methanamide or ameisensaeureamid, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Formamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Formamide, in its pure state, has been used as an alternative solvent for the electrostatic self-assembly of polymer nanofilms. Formamide exists in all living organisms, ranging from bacteria to humans. Outside of the human body, formamide has been detected, but not quantified in, several different foods, such as hyssops, rose hips, asian pears, brassicas, and green bell peppers. This could make formamide a potential biomarker for the consumption of these foods. It has been used as a softener for paper and fiber. Inhalation of large amounts of formamide vapor may require medical attention. In the past, formamide was produced by treating formic acid with ammonia, which produces ammonium formate, which in turn yields formamide upon heating:HCOOH + NH3 → HCOO−NH+4HCOO−NH+4 → HCONH2 + H2OFormamide is also generated by aminolysis of ethyl formate:HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OHThe current industrial process for the manufacture of formamide involves either the carbonylation of ammonia:CO + NH3 → HCONH2An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol:CO + CH3OH → HCOOCH3HCO2CH3 + NH3 → HCONH2 + CH3OHFormamide is used in the industrial production of hydrogen cyanide. Formamide has been shown to exhibit hematoxicity in animals and is considered hazardous by prolonged exposure through inhalation, oral intake and dermal absorption. |
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Structure | |
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Synonyms | Value | Source |
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Ameisensaeureamid | ChEBI | Carbamaldehyde | ChEBI | Formamid | ChEBI | Formimidic acid | ChEBI | Methanamid | ChEBI | Methanamide | ChEBI | Formimidate | Generator |
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Chemical Formula | CH3NO |
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Average Molecular Weight | 45.0406 |
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Monoisotopic Molecular Weight | 45.021463723 |
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IUPAC Name | formamide |
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Traditional Name | formamide |
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CAS Registry Number | 75-12-7 |
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SMILES | NC=O |
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InChI Identifier | InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) |
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InChI Key | ZHNUHDYFZUAESO-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboximidic acids and derivatives |
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Sub Class | Carboximidic acids |
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Direct Parent | Carboximidic acids |
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Alternative Parents | |
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Substituents | - Carboximidic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Imine
- 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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Disposition | Route of exposure: Source: Biological location: |
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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 | 2.55 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000 mg/mL | Not Available | LogP | -1.51 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9000000000-f6326cc6c67041284b52 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9000000000-4a58cc52ed1f85a41b4c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9000000000-52b8e3cce362934e1d52 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004j-9000000000-32c53cf62ffc73e10c84 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-0a22a0222cfe33823b8b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-2473e800b4396749f887 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004l-9000000000-3221c668103b22c85e42 | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022677 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 693 |
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KEGG Compound ID | C00488 |
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BioCyc ID | FORMAMIDE |
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BiGG ID | Not Available |
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Wikipedia Link | Formamide |
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METLIN ID | 4182 |
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PubChem Compound | 713 |
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PDB ID | Not Available |
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ChEBI ID | 16397 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Magill, P. L. Formamide. Journal of Industrial and Engineering Chemistry (Washington, D. C.) (1934), 26 611-14. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Lareo AC, Perbellini L: Biological monitoring of workers exposed to N-N-dimethylformamide. II. Dimethylformamide and its metabolites in urine of exposed workers. Int Arch Occup Environ Health. 1995;67(1):47-52. [PubMed:7622279 ]
- Kawashima K, Doi H, Ito Y, Shibata MA, Yoshinaka R, Otsuki Y: Evaluation of cell death and proliferation in psoriatic epidermis. J Dermatol Sci. 2004 Sep;35(3):207-14. [PubMed:15381242 ]
- Major J, Hudak A, Kiss G, Jakab MG, Szaniszlo J, Naray M, Nagy I, Tompa A: Follow-up biological and genotoxicological monitoring of acrylonitrile- and dimethylformamide-exposed viscose rayon plant workers. Environ Mol Mutagen. 1998;31(4):301-10. [PubMed:9654238 ]
- Al-Soud WA, Ouis IS, Li DQ, Ljungh S, Wadstrom T: Characterization of the PCR inhibitory effect of bile to optimize real-time PCR detection of Helicobacter species. FEMS Immunol Med Microbiol. 2005 May 1;44(2):177-82. [PubMed:15866213 ]
- Eizuru Y, Minamishima Y, Matsumoto T, Hamakado T, Mizukoshi M, Nabeshima K, Koono M, Yoshida A, Yoshida H, Kikuchi M: Application of in situ hybridization with a novel phenytoin-labeled probe to conventional formalin-fixed, paraffin-embedded tissue sections. J Virol Methods. 1995 Apr;52(3):309-16. [PubMed:7601905 ]
- Walrath J, Fayerweather WE, Gilby PG, Pell S: A case-control study of cancer among du pont employees with potential for exposure to dimethylformamide. J Occup Med. 1989 May;31(5):432-8. [PubMed:2715850 ]
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