Fluoroacetamide

Last updated
Fluoroacetamide
Fluoracetamide structural formula V.1.svg
Fluoroacetamide-3D-balls.png
Names
IUPAC name
2-Fluoroacetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.331 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C2H4FNO/c3-1-2(4)5/h1H2,(H2,4,5) Yes check.svgY
    Key: FVTWJXMFYOXOKK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H4FNO/c3-1-2(4)5/h1H2,(H2,4,5)
    Key: FVTWJXMFYOXOKK-UHFFFAOYAA
  • C(C(=O)N)F
  • FCC(=O)N
Properties
FCH2CONH2
Molar mass 77.058 g·mol−1
AppearanceColorless crystals
Melting point 107 to 109 °C (225 to 228 °F; 380 to 382 K)
Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Very toxic
GHS labelling:
GHS-pictogram-skull.svg
Danger
H300+H310
P262, P264, P270, P280, P301+P310+P330, P302, P350, P362, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability (yellow): no hazard codeSpecial hazards (white): no code
4
1
Lethal dose or concentration (LD, LC):
80 mg/kg (dermal, rat)
550 mg/m3(mouse, inhalation, dust/mist)
Safety data sheet (SDS) [1]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fluoroacetamide is an organic compound with the chemical formula F C H 2CO NH2. It is a compound based on acetamide with one fluorine atom replacing hydrogen on the methyl group. It is very toxic. [1] It is a metabolic poison which disrupts the citric acid cycle and was used as a rodenticide. [2] May cause reproductive disorders. If swallowed or in contact with skin, it can cause serious damage and death. Can cause serious eye damage. [1]

See also

Related Research Articles

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Sodium fluoroacetate, also known as compound 1080, is an organofluorine chemical compound with the chemical formula FCH2CO2Na. It is the sodium salt of fluoroacetic acid. It contains sodium cations Na+ and fluoroacetate anions FCH2CO−2. This colourless salt has a taste similar to that of table salt and is used as a rodenticide.

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<span class="mw-page-title-main">Fluoroacetic acid</span> Chemical compound

Fluoroacetic acid is a organofluorine compound with the chemical formula FCH2CO2H. It is a colorless solid that is noted for its relatively high toxicity. The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only five known organofluorine-containing natural products.

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<span class="mw-page-title-main">Diphenadione</span> Chemical compound

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<span class="mw-page-title-main">Haloacetate dehalogenase</span> Class of enzymes

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<i>Dichapetalum cymosum</i> Species of plant

Dichapetalum cymosum, commonly known as gifblaar from Afrikaans, or occasionally by its English translation, poison leaf, is a small prostrate shrub occurring in northern parts of Southern Africa in the family Dichapetalaceae. It is notable as a common cause of lethal cattle poisoning in this region and is considered one of the 'big 6' toxic plants of cattle in South Africa. A 1996 estimate of plant poisonings in South Africa attributes 8% of cattle mortality caused by poisonous plants to it. The majority (70%) of fatal cases are in Limpopo province, with 10% each in North West, Mpumalanga, and Gauteng. Fluoroacetate, the poison used to synthetically produce Compound 1080 used extensively in New Zealand, occurs in all parts of the plant and is responsible for the toxic effects shown.

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Fluoroacetyl chloride is an acyl chloride.

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<span class="mw-page-title-main">Methyl fluoroacetate</span> Chemical compound

Methyl fluoroacetate (MFA) is an organic compound with the chemical formula FCH2CO2CH3. It is the extremely toxic methyl ester of fluoroacetic acid. It is a colorless, odorless liquid at room temperature. It is used as a laboratory chemical and as a rodenticide. Because of its extreme toxicity, MFA was studied for potential use as a chemical weapon.

<span class="mw-page-title-main">Fluoroethyl fluoroacetate</span> Chemical compound

Fluoroethyl fluoroacetate, or more accurately 2-fluoroethyl fluoroacetate, is an organic compound with the chemical formula FCH2CO2CH2CH2F. It is the fluoroacetate ester of 2-fluoroethanol, or in other words, the 2-fluoroethyl ester of fluoroacetic acid. 2-Fluoroethyl fluoroacetate is two times more toxic than methyl fluoroacetate.

<span class="mw-page-title-main">Fluoroaspirin</span> Chemical compound

Fluoroaspirin is the fluoroacetate ester of salicylic acid. It is the fluoroacetate analog of aspirin. Like other fluoroacetate esters, fluoroaspirin is highly toxic.

4-Fluorobutanol is a chemical compound, a flammable colorless liquid which is a fluorinated alcohol. Like 2-fluoroethanol, it is highly toxic due to its ready metabolism to fluoroacetate.

<span class="mw-page-title-main">2C-T-28</span> Psychedelic drug

2C-T-28 is a lesser-known psychedelic drug related to compounds such as 2C-T-7 and 2C-T-21. It was named by Alexander Shulgin but was never made or tested by him, and was instead first synthesised by Daniel Trachsel some years later. It has a binding affinity of 75 nM at 5-HT2A and 28 nM at 5-HT2C. It is reportedly a potent psychedelic drug with an active dose in the 8–20 mg range, and a duration of action of 8–10 hours, with prominent visual effects. 2C-T-28 is the 3-fluoropropyl instead of 2-fluoroethyl chain-lengthened homologue of 2C-T-21 and has very similar properties, although unlike 2C-T-21 it will not form toxic fluoroacetate as a metabolite.

The Sanyao poisonings were a series of poisonings, some of which were fatal, in Sanyao Management District committed by Du Runqiong and Tang Youhua.

<span class="mw-page-title-main">2-Ethylhexyl fluoroacetate</span> Chemical compound

2-Ethylhexyl fluoroacetate is an organic compound with the chemical formula FCH2CO2CH2CH(CH2CH3)CH2CH2CH2CH3. It is the fluoroacetate ester of 2-ethylhexanol, in other words, the 2-ethylhexyl ester of fluoroacetic acid. It can be produced by reaction of ethyl fluoroacetate with 2-ethylhexanol. 2-Ethylhexyl fluoroacetate is a liquid that is highly toxic by skin absorption.

References

  1. 1 2 3 https://www.sigmaaldrich.com/US/en/sds/aldrich/128341?userType=anonymous [ bare URL ]
  2. MATSUMURA F, O'BRIEN RD. A COMPARATIVE STUDY OF THE MODES OF ACTION OF FLUOROACETAMIDE AND FLUOROACETATE IN THE MOUSE AND AMERICAN COCKROACH. Biochem Pharmacol. 1963 Oct;12:1201-5. doi : 10.1016/0006-2952(63)90095-9 PMID   14074120