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Record Information
Version2.0
Creation Date2009-08-12 14:05:03 UTC
Update Date2014-12-24 20:26:10 UTC
Accession NumberT3D3580
Identification
Common NameSodium fluoroacetate
ClassSmall Molecule
DescriptionSodium fluoroacetate is an organofluorine compound and a derivative of fluoroacetic acid. Sodium fluoroacetate is known under its brand name "1080". Sodium fluoroacetate occurs naturally as an anti-herbivore metabolite in various plants but can also be produced synthetically. Fluoroacetate is highly toxic to mammals and insects; it is used as a pesticide especially for mammalian pest species. The more common fluorinated acetic acid, trifluoroacetic acid and its sodium salt are far less toxic. (2)
Compound Type
  • Organic Compound
  • Organofluoride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Fluoroacetic acid sodium salt
Natriumfluoracetat
Sodium fluoroacetic acid
Sodium monofluoroacetate
Chemical FormulaC2H2FNaO2
Average Molecular Mass100.024 g/mol
Monoisotopic Mass99.994 g/mol
CAS Registry Number62-74-8
IUPAC Namesodium 2-fluoroacetate
Traditional Namesodium fluoroacetate
SMILES[Na+].[O-]C(=O)CF
InChI IdentifierInChI=1S/C2H3FO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1
InChI KeyInChIKey=JGFYQVQAXANWJU-UHFFFAOYSA-M
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Carboxylic acid salt
  • Organic metal halide
  • Carboxylic acid
  • Organic alkali metal salt
  • Monocarboxylic acid or derivatives
  • Alkyl fluoride
  • Organic salt
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Organic sodium salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alkyl halide
  • 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
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceOdourless white powder. (1)
Experimental Properties
PropertyValue
Melting Point200°C (325.15°K)
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility108.0 mg/mLALOGPS
logP0ALOGPS
logP-0.15ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)3.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.13 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.49 m3·mol-1ChemAxon
Polarizability5.04 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityFluoroacetate is similar to acetate, which has a pivotal role in cellular metabolism. Fluoroacetate disrupts the citric acid cycle by combining with coenzyme A to form fluoroacetyl CoA. Fluoroacetyl CoA then reacts with citrate synthase to produce fluorocitrate. A metabolite of fluorocitrate binds very tightly to aconitase, thereby halting the citric acid cycle. This inhibition results in an accumulation of citrate in the blood which deprives cells of energy. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsThe symptoms of sodium fluoroacetate poisoning normally appear between 30 minutes and three hours after exposure. Initial symptoms typically include nausea, vomiting and abdominal pain; sweating, confusion and agitation follow. In significant poisoning cardiac abnormalities including tachycardia or bradycardia, hypotension and ECG changes develop. Neurological effects include muscle twitching and seizures. Consciousness becomes progressively impaired after a few hours leading to coma. Death is generally due to ventricular arrhythmias, progressive hypotension unresponsive to treatment, and secondary lung infections. Sub-lethal doses of sodium fluoroacetate may cause damage to tissues with high energy needs, in particular, the brain, gonads, heart, lungs and fetus. Sub-lethal doses are typically completely metabolised and excreted within four days. (2)
TreatmentBecause of the biochemical interference in the citric acid cycle, sodium fluoroacetate poisoning is very difficult to treat. Once clinical symptoms are exhibited, the citric acid cycle has shut down. Effective antidotes are unknown. Research in animals has shown that the use of glyceryl monoacetate can prevent problems if given after ingestion of sodium fluoroacetate. In clinical cases, use of muscle relaxants, anti-convulsants, mechanical ventilation, and other supportive measures may all be required. Few animals or people have been treated successfully after significant sodium fluoroacetate ingestions. (2)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID16212360
ChEMBL IDCHEMBL369611
ChemSpider ID5893
KEGG IDC18588
UniProt IDNot Available
OMIM ID
ChEBI ID38699
BioCyc IDNot Available
CTD IDNot Available
Stitch IDSodium fluoroacetate
PDB IDNot Available
ACToR ID6534
Wikipedia LinkSodium_fluoroacetate
References
Synthesis ReferenceNot Available
MSDST3D3580.pdf
General References
  1. HSDB: Hazardous Substances Data Bank. National Library of Medicine (2001). [Link]
  2. Wikipedia. Sodium fluoroacetate. Last Updated 8 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available