Record Information |
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Version | 5.0 |
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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 | 2023-02-21 17:15:46 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, 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. Formamide has been detected, but not quantified in several different foods, such as hyssops, rose hips, asian pears, brassicas, and green bell peppers. 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 + H2O. Formamide is also generated by aminolysis of ethyl formate: HCOOCH2CH3 + NH3 → HCONH2 + CH3CH2OH. The current industrial process for the manufacture of formamide involves either the carbonylation of ammonia: CO + NH3 → HCONH2. An alternative two-stage process involves the ammonolysis of methyl formate, which is formed from carbon monoxide and methanol: CO + CH3OH → HCOOCH3HCO2CH3 + NH3 → HCONH2 + CH3OH. Formamide 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 | InChI=1S/CH3NO/c2-1-3/h1H,(H2,2,3) |
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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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Liquid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 113.476 | 30932474 | DeepCCS | [M-H]- | 111.654 | 30932474 | DeepCCS | [M-2H]- | 146.888 | 30932474 | DeepCCS | [M+Na]+ | 120.501 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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Formamide | NC=O | 1709.0 | Standard polar | 33892256 | Formamide | NC=O | 598.3 | Standard non polar | 33892256 | Formamide | NC=O | 709.7 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Formamide,1TMS,isomer #1 | C[Si](C)(C)NC=O | 837.9 | Semi standard non polar | 33892256 | Formamide,1TMS,isomer #1 | C[Si](C)(C)NC=O | 839.0 | Standard non polar | 33892256 | Formamide,1TMS,isomer #1 | C[Si](C)(C)NC=O | 1088.1 | Standard polar | 33892256 | Formamide,2TMS,isomer #1 | C[Si](C)(C)N(C=O)[Si](C)(C)C | 968.1 | Semi standard non polar | 33892256 | Formamide,2TMS,isomer #1 | C[Si](C)(C)N(C=O)[Si](C)(C)C | 966.9 | Standard non polar | 33892256 | Formamide,2TMS,isomer #1 | C[Si](C)(C)N(C=O)[Si](C)(C)C | 1039.3 | Standard polar | 33892256 | Formamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC=O | 1062.4 | Semi standard non polar | 33892256 | Formamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC=O | 1011.7 | Standard non polar | 33892256 | Formamide,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC=O | 1266.1 | Standard polar | 33892256 | Formamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C=O)[Si](C)(C)C(C)(C)C | 1381.1 | Semi standard non polar | 33892256 | Formamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C=O)[Si](C)(C)C(C)(C)C | 1355.6 | Standard non polar | 33892256 | Formamide,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C=O)[Si](C)(C)C(C)(C)C | 1290.8 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Formamide GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9000000000-f6326cc6c67041284b52 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Formamide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 10V, Positive-QTOF | splash10-0002-9000000000-4a58cc52ed1f85a41b4c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 20V, Positive-QTOF | splash10-0002-9000000000-52b8e3cce362934e1d52 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 40V, Positive-QTOF | splash10-004j-9000000000-32c53cf62ffc73e10c84 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 10V, Negative-QTOF | splash10-0006-9000000000-0a22a0222cfe33823b8b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 20V, Negative-QTOF | splash10-0006-9000000000-2473e800b4396749f887 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 40V, Negative-QTOF | splash10-004l-9000000000-3221c668103b22c85e42 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 10V, Positive-QTOF | splash10-0002-9000000000-e0e93b80e95c0e39a985 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 20V, Positive-QTOF | splash10-0002-9000000000-e0e93b80e95c0e39a985 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 40V, Positive-QTOF | splash10-0002-9000000000-a08824ab04647a23f4ad | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 10V, Negative-QTOF | splash10-0006-9000000000-451c209790660c80803f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 20V, Negative-QTOF | splash10-0006-9000000000-451c209790660c80803f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Formamide 40V, Negative-QTOF | splash10-0006-9000000000-ab072a75b4f755c7548c | 2021-09-23 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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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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