Fipronil
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Category | Animal Health |
Catalog number | BBF-05824 |
CAS | 120068-37-3 |
Molecular Weight | 437.15 |
Molecular Formula | C12H4Cl2F6N4OS |
Purity | > 95% |
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Description
Fipronil is a broad-spectrum insecticide that disrupts the insect central nervous system by blocking GABA-gated chloride channels and glutamate-gated chloride channels, resulting in central nervous system toxicity. Fipronil can be used to kill parasites such as fleas and lice on cats and dogs.
Specification
Synonyms | Fluocyanobenpyrazole; (RS)-5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile; 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile; (+/-)-Fipronil; 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-amino-4-(trifluoromethylsulfinyl)pyrazole; Frontline Spot-on; Frontline Spray; Frontline Top Spot; Goliath gel; Granedo MC; Grenade MC; Maxforce FC; Maxforce FC Select Roach Killer Bait Gel; Over'n Out; Regent; Regent TS; Termidor; Termidor 80WG; TopChoice; RM 1601; NSC-758960 |
Shelf Life | Limited shelf life, expiry date on the label |
Storage | Store at 2-8°C |
IUPAC Name | 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile |
Canonical SMILES | C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F |
InChI | InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2 |
InChI Key | ZOCSXAVNDGMNBV-UHFFFAOYSA-N |
Properties
Appearance | Off-White to Light Beige Solid |
Antibiotic Activity Spectrum | Parasites |
Boiling Point | 510.1±50.0°C(Predicted) |
Melting Point | 200-201°C |
Density | 1.55 g/cm3 |
Solubility | Soluble in DMSO (Slightly), Methanol (Very Slightly) |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | Fipronil blocks the passage of chloride ions through the GABA-regulated chloride channel, disrupting CNS activity. Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. |
Toxicity | Fipronil exposure in red-legged partridge (Alectoris rufa) altered blood biochemistry and sexual hormone levels and reduced cellular immune response, antioxidant levels, and carotenoid-based coloration. No skin irritation was observed in rabbits. Some signs of toxicity and body-weight loss were still evident when the observation period ended at day 7 after treatment. |
Reference Reading
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H4Cl2F6N4OS
Molecular Weight (Monoisotopic Mass): 435.9387 Da
Molecular Weight (Avergae Mass): 437.148 Da
LC-MS/MS Spectrum - LC-ESI-ITFT 30V, positive
Experimental Conditions
Collision Energy Level: low
Collision Energy Voltage: 30
Ionization Mode: positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H4Cl2F6N4OS
Molecular Weight (Monoisotopic Mass): 435.9387 Da
Molecular Weight (Avergae Mass): 437.148 Da
1H NMR Spectrum
Experimental Conditions
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2