Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-05 03:38:39 UTC |
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Update Date | 2014-12-24 20:25:43 UTC |
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Accession Number | T3D2578 |
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Identification |
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Common Name | Fluoroacetamide |
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Class | Small Molecule |
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Description | Fluoroacetamide is an organic compound based on acetamide with one fluorine atom replacing hydrogen on the methyl group. it is a metabolic poison which disruptes the citric acid cycle and is used as a rodenticide (10). |
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Compound Type | - Amide
- Amine
- Organic Compound
- Organofluoride
- Pesticide
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 2-Fluoroacetamide | Amid kyseliny fluoroctove | Baran | Caswell No. 461 | Compound 1081 | FAA | Fluoracetamide | Fluorakil 100 | Fluorkill | Fluoroacetic acid amide | Fluoroakil 100 | Flutritex 1 | Fussol | Megatox | Monofluoroacetamide | Navron | RCRA waste no. P057 | Rcra waste number P057 | Rodex | Sjyhcahiktp | WLN: ZV1F | Yanock |
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Chemical Formula | C2H4FNO |
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Average Molecular Mass | 77.058 g/mol |
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Monoisotopic Mass | 77.028 g/mol |
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CAS Registry Number | 640-19-7 |
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IUPAC Name | 2-fluoroacetamide |
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Traditional Name | fluoroacetamide |
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SMILES | NC(=O)CF |
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InChI Identifier | InChI=1S/C2H4FNO/c3-1-2(4)5/h1H2,(H2,4,5) |
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InChI Key | InChIKey=FVTWJXMFYOXOKK-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
- Organofluoride
- Organohalogen compound
- Alkyl halide
- Alkyl fluoride
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | Colorless crystalline powder (2). |
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Experimental Properties | Property | Value |
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Melting Point | 108°C | Boiling Point | Not Available | Solubility | 1000 mg/mL at 25°C [SHIU,WY et al. (1990)] | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-055f-9000000000-c8a80376eab4591e6d8e | 2021-09-24 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-37f476ac4fd393f38857 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fr-9000000000-293daf3ed0380e544a76 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9000000000-f26325b6f3d1b090b190 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9000000000-ed6d07fc91ad13cd2f80 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004l-9000000000-e1fd8dc842ea98819299 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-390e391add50e5b35eca | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-4db14b39c7eff29fd2a6 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-9000000000-7b4cd69bfe0c1fd6a723 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9000000000-37504159be9b6ee520bf | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9000000000-60c6b92e2ad696958b27 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-e818ef43533dfed1bdd4 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-90726b17dc36e29c5299 | 2021-10-12 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0006-9000000000-1e4f4c231915f4e50698 | 2014-09-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, experimental) | Not Available | 2014-09-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-10-13 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Inhalation (9) ; oral (9) ; dermal (9) ; eye contact (9). |
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Mechanism of Toxicity | Fluoroacetate produces its toxin action by inhibiting the citric acid cycle. The fluorine substituted acetate becomes incorporated, as a normal acetate, into fluoroacetyl coenzyme A, which condenses with oxaloacetate to form fluorocitrate. Fluorocitrate inhibits the enzyme aconitase and thereby inhibits the conversion of citrate to isocitrate. As a result there is an accumulation of large quantities of citrate in the tissue, and the cycle is blocked. The heart and CNS are the most critical tissues involved in poisoning by general inhibition of oxydative energy metabolism (3). |
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Metabolism | Fluoroacetamide is metabolized by the fluoroacetate specific dehalogenase (1). |
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Toxicity Values | LD50: 4-15 mg/kg (Oral, Rat) (3)
LD50: 80 mg/kg (Dermal, Rat) (4) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Used as rodenticide, insecticide proposed mainly for use on fruits to combat scale insects, aphids, mites (6). |
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Minimum Risk Level | Not Available |
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Health Effects | Metabolic acidosis, hyperglycemia, hyperuricemia, elevated serum levels of hepatic transaminases, and elevated serum creatinine levels may occur. Tachycardia, ventricular tachycardia or fibrillation, and sudden onset of asystole may occur (5).
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Symptoms | Nausea, vomiting, excessive salivation, abdominal pain, numbness, a tingling sensation, and apprehension are seen initially, and may last for up to 6 hours. Numbness and tingling of the face, excessive salivation, blurred vision, peripheral paresthesias, convulsions, and coma followed inhalation and dermal contact with fluoroacetate (5). |
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Treatment | Consider gastric lavage after ingestion, and/or administer charcoal as a slurry. In case of refractory seizures after following ingestion, consider continuous infusion of midazolam, propofol, and/or pentobarbital. Hyperthermia, lactic acidosis and muscle destruction may necessitate use of neuromuscular blocking agents with continuous EEG monitoring. If the exposure occurred through inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of acute lung injury, maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (5) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 12542 |
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ChEMBL ID | CHEMBL160811 |
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ChemSpider ID | 12025 |
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KEGG ID | C18675 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 53124 |
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BioCyc ID | Not Available |
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CTD ID | C007741 |
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Stitch ID | Fluoroacetamide |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D2578.pdf |
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General References | - Kostyniak PJ, Soiefer AI: The role of fluoroacetate-specific dehalogenase and glutathione transferase in the metabolism of fluoroacetamide and 2,4-dinitrofluorobenzene. Toxicol Lett. 1984 Aug;22(2):217-22. [6147909 ]
- Juhila J, Honkanen A, Sallinen J, Haapalinna A, Korpi ER, Scheinin M: alpha(2A)-Adrenoceptors regulate d-amphetamine-induced hyperactivity and behavioural sensitization in mice. Eur J Pharmacol. 2005 Jul 4;517(1-2):74-83. [15978573 ]
- Lott DC, Kim SJ, Cook EH Jr, de Wit H: Dopamine transporter gene associated with diminished subjective response to amphetamine. Neuropsychopharmacology. 2005 Mar;30(3):602-9. [15602501 ]
- Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
- Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
- Budavari, S (ed) (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.
- Tomlin CDS (ed) (1997). The Pesticide Manual - World Compendium. 11th ed. Surrey, UK: British Crop Protection Council, Surrey, England.
- Doull J, Klassen CD, and Amdur MD (eds) (1986). Casarett and Doull's Toxicology. 3rd ed. New York: Macmillan Co., Inc.
- Wikipedia. Tramadol. Last Updated 8 August 2009. [Link]
- Wikipedia. Fluoroacetamide. Last Updated 25 January 2009. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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