26675-46-7 Hazards Identification
Pictogram(s):
Signal:
Warning
GHS Hazard Statements:
H336 (100%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]
H373 (80.81%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
Precautionary Statement Codes:
P260, P261, P271, P304+P340, P319, P403+P233, P405, and P501
Hazard Classes and Categories:
STOT SE 3 (100%)
STOT RE 2 (80.81%)
Hazards Summary:
A skin, eye, and respiratory tract irritant; May cause CNS and cardiovascular system effects; [ICSC] Occupational asthma confirmed three workers exposed to Sevoflurane and Isoflurane; [Malo] 2021 TLV Basis: embryo damage, maternal body weight effects, CNS impairment; [ACGIH] Mice exposed to concentrations of 0.6% for 4hr/day during gestation produced smaller litters, delayed ossification, and increased frequency of cleft palate (maternal toxicity shown by weight reduction); Chronic exposure of mice to low anesthetic or sub-anesthetic doses demonstrated no evidence of effects male or female fertility, reproductive loss, or early postnatal fetal wastage; A more recent study associated chronic exposure with fetal growth retardation; Chronic exposure in rabbits produced significantly reduced sperm concentrations and motility; [REPROTOX] May cause drowsiness or dizziness; [Abbott Laboratories MSDS]
26675-46-7 Usage
Uses
Used in Anesthesia:
Isoflurane is used as an inhalational anesthetic agent for inducing and maintaining anesthesia during surgical procedures. Its rapid onset and recovery make it a popular choice among anesthesiologists.
Used in Research:
Isoflurane is utilized in the study of its interaction with biological systems, providing valuable insights into the mechanisms of anesthesia and potential applications in medical research.
Used in Veterinary Medicine:
Isoflurane is also used as an anesthetic agent in veterinary medicine, offering a safe and effective means of anesthesia for various animal species.
Used as a Solvent and Dispersant:
In the industrial sector, isoflurane serves as a solvent and dispersant for fluorinated materials, contributing to the manufacturing and processing of these specialized compounds.
Used in Postoperative Cognitive Dysfunction Studies:
Recent studies have explored the potential relationship between isoflurane administration and postoperative cognitive dysfunction (POCD), aiming to understand the long-term effects of anesthesia on cognitive function.
Originator
Forane,Ohio Medical,US,1980
Manufacturing Process
A 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.
Therapeutic Function
Inhalation anesthetic
Biological Functions
Isoflurane (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.
Biochem/physiol Actions
Isoflurane 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 Use
Isoflurane 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 Treatments
Isoflurane 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.
Check Digit Verification of cas no
The CAS Registry Mumber 26675-46-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,6,7 and 5 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 26675-46:
(7*2)+(6*6)+(5*6)+(4*7)+(3*5)+(2*4)+(1*6)=137
137 % 10 = 7
So 26675-46-7 is a valid CAS Registry Number.
InChI:InChI=1/C14HF29O4/c15-1(2(16,17)18)44-12(38,39)4(21,8(27,28)29)46-14(42,43)6(23,10(33,34)35)47-13(40,41)5(22,9(30,31)32)45-11(36,37)3(19,20)7(24,25)26/h1H
26675-46-7Relevant academic research and scientific papers
METHOD FOR PRODUCING HALOGENATED ETHER
-
Paragraph 0116; 0117, (2020/03/05)
PROBLEM TO BE SOLVED: To provide a method for producing 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (isoflurane) or 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) useful as an inhaled anesthetic, on an industrial scale with high efficie
Preparation method of isoflurane
-
Paragraph 0021; 0034; 0036-0037; 0039-0040; 0042-0043; 0045, (2020/12/15)
The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of isoflurane. The method for preparing the isoflurane comprises the following steps:taking Freon 22 as a raw material to obtain difluoromet
Improvements in or relating to contrast agents
-
, (2008/06/13)
Combined preparations comprising an injectable gas dispersion and a coadministrable diffusible component which is capable of inward diffusion into the dispersed gas so as to promote temporary growth of the gas in vivo, the preparations being for use as contrast agents in ultrasound cardiac studies of patients who have undergone physical exercise-induced stress in order to promote vasodilatation.
Diisopropylethylamine mono(hydrogen fluoride) for nucleophilic fluorination of sensitive substrates: Synthesis of sevoflurane
Kudzma,Huang,Lessor,Rozov,Afrin,Kallashi,McCutcheon,Ramig
, p. 11 - 16 (2007/10/03)
Diisopropylethylamine mono(hydrogen fluoride) (8), which can be prepared by addition of two equivalents of diisopropylethylamine to the complex diisopropylethylamine tris(hydrogen fluoride) (7), is shown to be an effective and selective nucleophilic fluorinating reagent when applied to halogen-exchange reactions of chloromethyl ethers, in particular the conversion of 1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether (3) to the volatile anesthetic sevoflurane (1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether). The amine portion of the reagent does not react with the starting material to give a troublesome quaternary ammonium salt, as is the case for the species formed by addition of two equivalents of triethylamine to triethylamine tris(hydrogen fluoride). These particular chloromethyl ether substrates require a 1:1 stoichiometry of diisopropylethylamine to hydrogen fluoride to give useful rates of reaction and yields when solventless conditions are desired. Two other complexes, diisopropylethylamine bis(hydrogen fluoride) and 7, are ineffective for conversion of 3 to sevoflurane.
Process for the manufacture of halo esters of carboxylic or dicarboxylic acids
-
, (2008/06/13)
A compound (Ia) or (Ib) is prepared by reacting, in a polar aprotic solvent, a compound (III) with a salt of a carboxylic or dicarboxylic acid (IIa) or (IIb). The reaction may be carried out under pressure, but also at normal atmospheric pressure or in the region of normal atmospheric pressure (especially between 0.10 bar and 2 bars). The product (Ia) or (Ib) formed is, in this latter case, recovered continuously as it is formed. STR1 R1, R2 =optionally substituted saturated or unsaturated acyclic or cyclic hydrocarbon radicals; R3 =C1 -C10 perhaloalkyl; 0n≤4; X=halogen. The applications of the fluoroalkyl (meth)acrylates obtained are especially: anti-dust or anti-soiling paints for various supports such as exterior coatings and metal furniture; optical fibers; contact lenses; lithography; electrophotography; heat-resistant materials; dental resins.
The fluoromethyl ether sevoflurane as a fluoride source in halogen-exchange reactions 1
Rozov, Leonid A.,Lessor, Ralph A.,Kudzma, Linas V.,Ramig, Keith
, p. 51 - 54 (2007/10/03)
Fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether (sevoflurane), fluoromethyl 1,1,2,3,3,3-hexafluoropropyl ether, and fluoromethyl 1,2,2,2-tetrafluoroethyl ether are found to be selective fluoride donors in some halogen-exchange reactions. For example, treatment of a mixture of a polychlorinated substrate and one equivalent of sevoflurane with a catalytic amount of antimony pentachloride gives a monofluorinated product and one equivalent of chloromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether as by-product.
Selective free-radical dechlorination of 1,1-dichloro-2,2,2-trifluoroethyl difluoromethyl ether initiated thermally or by UV light: A practical and 'green' method for isoflurane synthesis
Ramig, Keith,Quiroz, Fernando,Vernice, Gerald G.,Rozov, Leonid A.
, p. 101 - 104 (2007/10/03)
Treatment of 1,1-dichloro-2,2,2-trifluoroethyl difluoromethyl ether (3) with 2-propanol followed by either irradiation with UV light or heating with radical initiators gives the inhalational anesthetic isoflurane. Unlike most other common dechlorination methods, monoreduction is the exclusive process and the by-products acetone and HC1 are relatively benign. Some comments about the mechanism of the reduction will be presented, along with solutions to problems encountered during scale-up.
Process for adjusting the halogen content of halogenated aliphatic ethers
-
, (2008/06/13)
Process for adjusting the halogen content of halogenated aliphatic ethers, by selective replacement of a halide substituent on the ether with a hydrogen. The process is particularly useful for the production of certain inhalant anesthetics.
Deuterated isoflurane as an anesthetic agent
-
, (2008/06/13)
Deuterated Isoflurane and anesthetic compositions thereof useful as inhalation anesthetics show reduced levels of inorganic fluoride in urine of anesthetized animals.
