Isoflurane

Isoflurane Basic information
Product Name:Isoflurane
Synonyms:ether,1-chloro-2,2,2-trifluoroethyldifluoromethyl;Forene;r-e235dal;1-Chloro-2,2,2-trifluoroethyl difluoromethyl ether 99%;1-Chloro-2,2,2-trifluoroethyldifluoromethylether99%;2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-ethan;Aerrane;chloro-2-(difluoromethoxy)-1,1,1-trifluoroethane
CAS:26675-46-7
MF:C3H2ClF5O
MW:184.49
EINECS:247-897-7
Product Categories:
Mol File:26675-46-7.mol
Isoflurane Structure
Isoflurane Chemical Properties
Melting point 48.5°C
Boiling point 48.5 °C
density 1.510 g/mL at 25 °C
vapor pressure 238 mmHg ( 20 °C)
refractive index 1.3002
Fp 48-49°C
storage temp. 2-8°C
solubility Practically insoluble in water, miscible with ethanol and trichloroethylene.
form neat
Specific Gravityapproximate 1.50
color Colorless to Almost colorless
Water Solubility Soluble in chloroform and ethyl acetate. Not miscible or difficult to mix in water.
Merck 14,5175
BRN 1852087
Stability:Stable.
InChIKeyPIWKPBJCKXDKJR-UHFFFAOYSA-N
CAS DataBase Reference26675-46-7(CAS DataBase Reference)
NIST Chemistry Reference1-Chloro-2,2,2-trifluoroethyl difluoromethyl ether(26675-46-7)
EPA Substance Registry SystemIsoflurane (26675-46-7)
Safety Information
Hazard Codes F,T,Xn
Risk Statements 36/37/38-67-48/20
Safety Statements 26-36/37/39-24/25
RIDADR UN 3334
WGK Germany 3
RTECS KN6799000
Hazard Note Flammable/Toxic
HS Code 2909191800
Hazardous Substances Data26675-46-7(Hazardous Substances Data)
ToxicityAn isomer of enflurane with similar anesthetic properties. Isoflurane has less effect on myocardial function, leaving the cardiovascular system normally responsive to epinephrine or hypercarbia, and it does not cause a marked increase in seizure susceptibility. It was not widely used because of reports that it caused increases in liver neoplasms in mice, but this observation has been challenged and the compound reintroduced.
MSDS Information
ProviderLanguage
ALFA English
Isoflurane Usage And Synthesis
Chemical Propertiescolourless liquid
OriginatorForane,Ohio Medical,US,1980
UsesSolvent and dispersant for fluorinated materials.
UsesIsoflurane is a volatile anesthetic agent mainly used to study its interaction with the biological system.
UsesIsoflurane is a halogenated ether used for inhalational anesthesia. Recent studies suggest that there might be a relationship between administration of isoflurane and postoperative cognitive dysfunct ion (POCD).
DefinitionChEBI: Isoflurane is an organofluorine compound. It has a role as an inhalation anaesthetic. It is functionally related to a methoxyethane.
Manufacturing ProcessA 1-liter 3-necked stainless steel flask was fitted with a copper "Dry Ice" cold finger condenser, a stainless steel stirring shaft and gland and a copper gas inlet tube. To the flask there was then added 50 g (0.23 mol) of CF3CHClOCHCl2 and 1.5 g of SbCl5 · HF gas was then slowly bubbled through the stirred mixture which was maintained at 0°C. The reaction was run until 0.35 mol of HCl was collected, as indicated by the titration of the effluent gas which was dissolved in water. Following the fluorination 26 g of material were recovered and determined to be 90% pure by vapor phase chromatography. Fractional distillation using a 30 x 0.5 cm column packed with glass helices gave the pure product, BP 48°C to 48.5°C.
Brand nameForane (Baxter Healthcare).
Therapeutic FunctionInhalation anesthetic
Biological FunctionsIsoflurane (Forane) is a structural isomer of enflurane and produces similar pharmacological properties: some analgesia, some neuromuscular blockade, and depressed respiration. In contrast, however, isoflurane is considered a particularly safe anesthetic in patients with ischemic heart disease, since cardiac output is maintained, the coronary arteries are dilated, and the myocardium does not appear to be sensitized to the effects of catecholamines. Also, blood pressure falls as a result of vasodilation, which preserves tissue blood flow. Isoflurane causes transient and mild tachycardia by direct sympathetic stimulation; this is particularly important in the management of patients with myocardial ischemia.
Unlike enflurane, isoflurane does not produce a seizurelike EEG pattern. Furthermore, the metabolic transformation of isoflurane is only one-tenth that of enflurane, so fluoride production is quite low. Among the halogenated hydrocarbons, isoflurane is one of the most popular, since it preserves cardiovascular stability and causes a low incidence of untoward effects.
General DescriptionIsoflurane is a volatile liquid (bp=48.5°C) with an MAC of1.15, a blood:gas partition coefficient of 1.43 and high solubilityin fat. Isoflurane is a structural isomer of enflurane. Itis a known respiratory irritant, but less so than desflurane.Approximately 0.2% of the administered drug undergoesmetabolism, the rest is exhaled unchanged. The metabolismof isoflurane yields low levels of the nephrotoxic fluoride ionas well as a potentially hepatotoxic trifluoroacetylating compound). The relatively low concentrations ofthese compounds have resulted in very low risks of hepatotoxicityand nephrotoxicity. There have been no reports ofseizures caused by isoflurane and only transient increases inheart rate have been reported.
Biochem/physiol ActionsIsoflurane is a tandem pore potassium channel activator. It is also a very widely used anesthetic for animal research and for in vitro studies on anesthesia mechanisms.
Clinical UseIsoflurane was introduced in the United States in 1981 and is a potent anesthetic agent with many similarities to its isomer enflurane (potent, nonflammable, and intermediate blood solubility). It does produce significantly fewer cardiovascular effects than enflurane, however, and it can be used safely with epinephrine without as great a concern for arrhythmia production. Isoflurane has a more pungent odor than halothane and, thus, can cause irritation to the throat and respiratory tract, triggering coughing and laryngospasm. To overcome this problem, it often is supplemented with intravenous agents. Less than 0.2% of an administered dose is metabolized, mostly to fluoride and trifluoroacetic acid. Some minimal potential for hepatotoxicity is associated with a trifluoroacetyl halide metabolite.
Veterinary Drugs and TreatmentsIsoflurane is an inhalant anesthetic that has some distinct advantages over either halothane or methoxyflurane due to its lessened myocardial depressant and catecholamine sensitizing effects, and the ability to use it safely in patients with either hepatic or renal disease. Isoflurane’s higher cost than either methoxyflurane or halothane is a disadvantage.
Horses may recover more rapidly than with halothane, but be more susceptible to anesthetic associated- myopathy.
1,1-DICHLORO-2,2,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER 1,1-DICHLORO-2,2,2-TRIFLUOROETHYL CHLORODIFLUOROMETHYL ETHER (R)-Isoflurane,R-(-)-Isoflurane compound 485 DIFLUOROMETHYL 2,2,2-TRIFLUOROETHYL ETHER 2,2,2-TrifluoroethyldifluoroMethyl Ether Isoflurane,InhalationAnesthetic ISOFLURANE RELATED COMPOUND A (0.1 ML) (1-CHLORO-2,2,2-TRIFLUOROETHYL CHLORODIFLUOROMETHYL ETHER) ETHYL METHYL ETHER C8E3 ISOFLURANE - REFERENCE SPECTRUM ISOFLURANE IMP. F (EP): ACETONE difluoroethane (S)-Isoflurane,S-(+)-Isoflurane ISOFLURANE RELATED COMPOUND B (0.1 ML) (2,2,2-TRIFLUOROETHYLDIFLUOROMETHYL ETHER) ISOFLURANE IMP. E (EP):1,1-DICHLORO-1-(CHLORODIFLUOROMETHOXY)-2,2,2-TRIFLUOROETHANE 2-CHLORO-2-(CHLORODIFLUOROMETHOXY)-1,1,1-TRIFLUOROETHANE 1,1,1-Trifluoroethane

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