T3DB: Sodium fluoroacetate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation XML

Record Information

Version

2.0

Creation Date

2009-08-12 14:05:03 UTC

Update Date

2014-12-24 20:26:10 UTC

Accession Number

T3D3580

Identification

Common Name

Sodium fluoroacetate

Class

Small Molecule

Description

Sodium 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

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Fluoroacetic acid sodium salt
Natriumfluoracetat
Sodium fluoroacetic acid
Sodium monofluoroacetate

Chemical Formula

C₂H₂FNaO₂

Average Molecular Mass

100.024 g/mol

Monoisotopic Mass

99.994 g/mol

CAS Registry Number

62-74-8

IUPAC Name

sodium 2-fluoroacetate

Traditional Name

sodium fluoroacetate

SMILES

[Na+].[O-]C(=O)CF

InChI Identifier

InChI=1S/C2H3FO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1

InChI Key

InChIKey=JGFYQVQAXANWJU-UHFFFAOYSA-M

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Alpha-halocarboxylic acids and derivatives

Direct Parent

Alpha-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 Framework

Aliphatic acyclic compounds

External Descriptors

organic sodium salt (CHEBI:38699 )
Organofluorine rodenticides (C18588 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

rodenticide

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Odourless white powder. (1)

Experimental Properties

Property	Value
Melting Point	200°C (325.15°K)
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	108 g/L	ALOGPS
logP	0	ALOGPS
logP	-0.15	ChemAxon
logS	0.03	ALOGPS
pKa (Strongest Acidic)	3.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	23.49 m³·mol⁻¹	ChemAxon
Polarizability	5.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-6900000000-569a907c8575fb953c9d	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-9500000000-f6612ed8e54151211376	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c38f4fc2aa6d983aaf82	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-b1353035c7679a46035c	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-ec2e810004e52259cc30	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9000000000-69a83ef6cd4d50dd12c6	2019-02-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, experimental)	Not Available	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Fluoroacetate 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)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

The 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)

Treatment

Because 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

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

16212360

ChEMBL ID