ContaminantDB: Fluoroacetamide

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

Record Information

Version

1.0

Creation Date

2009-07-05 03:38:39 UTC

Update Date

2026-03-27 00:42:12 UTC

Accession Number

CHEM002102

Identification

Common Name

Fluoroacetamide

Class

Small Molecule

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 (5).

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Organic Compound
Organofluoride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Fluoracetamide	ChEBI
Fluoroacetic acid amide	ChEBI
Monofluoroacetamide	ChEBI
Fluoroacetate amide	Generator

Chemical Formula

C₂H₄FNO

Average Molecular Mass

77.058 g/mol

Monoisotopic Mass

77.028 g/mol

CAS Registry Number

640-19-7

IUPAC Name

2-fluoroacetamide

Traditional Name

fluoroacetamide

SMILES

NC(=O)CF

InChI Identifier

InChI=1S/C2H4FNO/c3-1-2(4)5/h1H2,(H2,4,5)

InChI Key

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic 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 Framework

Aliphatic acyclic compounds

External Descriptors

2-fluoroacetamides (CHEBI:53124 )
Organofluorine rodenticides (C18675 )

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

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless crystalline powder (2).

Experimental Properties

Property	Value
Melting Point	108°C
Boiling Point	Not Available
Solubility	1000 mg/mL at 25°C [SHIU,WY et al. (1990)]

Predicted Properties

Property	Value	Source
Water Solubility	136 g/L	ALOGPS
logP	-0.64	ALOGPS
logP	-0.96	ChemAxon
logS	0.25	ALOGPS
pKa (Strongest Acidic)	12.95	ChemAxon
pKa (Strongest Basic)	-9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	14.48 m³·mol⁻¹	ChemAxon
Polarizability	5.84 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-055f-9000000000-c8a80376eab4591e6d8e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-37f476ac4fd393f38857	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-9000000000-293daf3ed0380e544a76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9000000000-f26325b6f3d1b090b190	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-ed6d07fc91ad13cd2f80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-9000000000-e1fd8dc842ea98819299	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-390e391add50e5b35eca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-9000000000-4db14b39c7eff29fd2a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-7b4cd69bfe0c1fd6a723	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-37504159be9b6ee520bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-60c6b92e2ad696958b27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-e818ef43533dfed1bdd4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-1e4f4c231915f4e50698	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (4) ; oral (4) ; dermal (4) ; eye contact (4).

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).

Metabolism

Fluoroacetamide is metabolized by the fluoroacetate specific dehalogenase (1).

Toxicity Values

LD50: 4-15 mg/kg (Oral, Rat) (3) LD50: 80 mg/kg (Dermal, Rat) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Used as rodenticide, insecticide proposed mainly for use on fruits to combat scale insects, aphids, mites (8).

Minimum Risk Level

Not Available

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 (7).

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 (7).

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. (7)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0252368

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Fluoroacetamide

Chemspider ID

12025

ChEBI ID

53124

PubChem Compound ID

Not Available

Kegg Compound ID

C18675

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Fluoroacetamide (CHEM002102)

Structure for CHEM002102: Fluoroacetamide