Record Information
Version2.0
Creation Date2009-07-05 03:38:39 UTC
Update Date2014-12-24 20:25:43 UTC
Accession NumberT3D2578
Identification
Common NameFluoroacetamide
ClassSmall Molecule
DescriptionFluoroacetamide 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).
Compound Type
  • Amide
  • Amine
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
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
Chemical FormulaC2H4FNO
Average Molecular Mass77.058 g/mol
Monoisotopic Mass77.028 g/mol
CAS Registry Number640-19-7
IUPAC Name2-fluoroacetamide
Traditional Namefluoroacetamide
SMILESNC(=O)CF
InChI IdentifierInChI=1S/C2H4FNO/c3-1-2(4)5/h1H2,(H2,4,5)
InChI KeyInChIKey=FVTWJXMFYOXOKK-UHFFFAOYSA-N
Chemical Taxonomy
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceColorless crystalline powder (2).
Experimental Properties
PropertyValue
Melting Point108°C
Boiling PointNot Available
Solubility1000 mg/mL at 25°C [SHIU,WY et al. (1990)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility136 g/LALOGPS
logP-0.64ALOGPS
logP-0.96ChemAxon
logS0.25ALOGPS
pKa (Strongest Acidic)12.95ChemAxon
pKa (Strongest Basic)-9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity14.48 m³·mol⁻¹ChemAxon
Polarizability5.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-055f-9000000000-c8a80376eab4591e6d8e2021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-37f476ac4fd393f388572016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-9000000000-293daf3ed0380e544a762016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9000000000-f26325b6f3d1b090b1902016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-ed6d07fc91ad13cd2f802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-9000000000-e1fd8dc842ea988192992016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-390e391add50e5b35eca2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-9000000000-4db14b39c7eff29fd2a62021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9000000000-7b4cd69bfe0c1fd6a7232021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-37504159be9b6ee520bf2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-60c6b92e2ad696958b272021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e818ef43533dfed1bdd42021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-90726b17dc36e29c52992021-10-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-1e4f4c231915f4e506982014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-10-13View Spectrum
Toxicity Profile
Route of ExposureInhalation (9) ; oral (9) ; dermal (9) ; eye contact (9).
Mechanism of ToxicityFluoroacetate 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).
MetabolismFluoroacetamide is metabolized by the fluoroacetate specific dehalogenase (1).
Toxicity ValuesLD50: 4-15 mg/kg (Oral, Rat) (3) LD50: 80 mg/kg (Dermal, Rat) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as rodenticide, insecticide proposed mainly for use on fruits to combat scale insects, aphids, mites (6).
Minimum Risk LevelNot Available
Health EffectsMetabolic 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).
SymptomsNausea, 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).
TreatmentConsider 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)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID12542
ChEMBL IDCHEMBL160811
ChemSpider ID12025
KEGG IDC18675
UniProt IDNot Available
OMIM ID
ChEBI ID53124
BioCyc IDNot Available
CTD IDC007741
Stitch IDFluoroacetamide
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D2578.pdf
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  5. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  6. Budavari, S (ed) (1996). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc.
  7. Tomlin CDS (ed) (1997). The Pesticide Manual - World Compendium. 11th ed. Surrey, UK: British Crop Protection Council, Surrey, England.
  8. Doull J, Klassen CD, and Amdur MD (eds) (1986). Casarett and Doull's Toxicology. 3rd ed. New York: Macmillan Co., Inc.
  9. Wikipedia. Tramadol. Last Updated 8 August 2009. [Link]
  10. Wikipedia. Fluoroacetamide. Last Updated 25 January 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available