Enflurane

Base Information

• Chemical Name: Enflurane
• CAS No.: 13838-16-9
• Molecular Formula: C3H2 Cl F5 O
• Molecular Weight: 184.493
• Hs Code.: 2909191800
• European Community (EC) Number: 237-553-4
• ICSC Number: 0887
• NSC Number: 115944
• UNII: 91I69L5AY5
• DSSTox Substance ID: DTXSID1020562
• Nikkaji Number: J3.127E
• Wikipedia: Enflurane
• Wikidata: Q416740
• NCI Thesaurus Code: C47511
• Pharos Ligand ID: GF55ZTJCSZAF
• Metabolomics Workbench ID: 53155
• ChEMBL ID: CHEMBL1257
• Mol file: 13838-16-9.mol

Synonyms:Alyrane;Enflurane;Enfran;Enlirane;Ethrane;Etran

Chemical Property of Enflurane

Chemical Property:

• Vapor Pressure: 272mmHg at 25°C
• Refractive Index: 1.303
• Boiling Point: 59.9°Cat760mmHg
• Flash Point: °C
• PSA: 9.23000
• Density: 1.489g/cm³
• LogP: 2.35280
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 183.9714332
• Heavy Atom Count: 10
• Complexity: 107

Purity/Quality:

99.0% ^*data from raw suppliers

Enflurane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Volatile with anesthetic properties, but nonflammable. TLV: 75 ppm; not classifiable as a human carcinogen.
• Hazard Codes: F,T,Xi
• Statements: 36
• Safety Statements: 23-26-36-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Waste Anesthetic Gases
• Drug Classes: Anesthetics, Halogenated
• Canonical SMILES: C(C(OC(F)F)(F)F)(F)Cl
• Recent ClinicalTrials: Vasodilation Effect of Inhalational Anesthetics
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system and cardiovascular system. Exposure at high levels could cause unconsciousness.
• Uses: Anesthetic in clinical anesthesia Clinical anesthetic. Ethrane is widely used clinically as an anes thesia (by inhalation). Workers in operatingrooms are susceptible to inhaling this compound at low concentrations.
• Therapeutic Function: Anesthetic
• Biological Functions: Enflurane (Ethrane) depresses myocardial contractility and lowers systemic vascular resistance. In contrast to halothane, it does not block sympathetic reflexes, and therefore, its administration results in tachycardia. However, the increased heart rate is not sufficient to oppose enflurane’s other cardiovascular actions, so cardiac output and blood pressure fall. In addition, enflurane sensitizes the myocardium to catecholamine-induced arrhythmias, although to a lesser extent than with halothane. Enflurane depresses respiration through mechanisms similar to halothane’s and requires that the patient’s ventilation be assisted. Neuromuscular transmission is depressed by enflurane, resulting in some skeletal muscle paralysis.Although muscle relaxation is inadequate for many surgical procedures, the anesthetic enhances the action of neuromuscular blocking agents, thereby lowering the dose of the paralytic agent needed and minimizing side effects. Deep anesthesia with enflurane is associated with the appearance of seizurelike electroencephalographic (EEG) changes. Occasionally frank tonic–clonic seizures are observed. Consequently, other inhalational agents are usually given to patients with preexisting seizure disorders. Another concern associated with the use of enflurane is its biotransformation, which leads to increased plasma fluoride. Following lengthy procedures in healthy patients, fluoride may reach levels that result in a mild reduction in renal concentrating ability.Thus, enflurane should be used cautiously in patients with clinically significant renal disease.
• Clinical Use: Enflurane was introduced into medical practice in the United States in 1973 and is a clear, colorless, nonflammable general liquid with a mild, sweet odor. Although relatively stable chemically, enflurane does not attack aluminum, copper, iron, or brass and is soluble in rubber (partition coefficient = 74), which can prolong induction/recovery times, as seen with halothane.Enflurane has an intermediate solubility in blood and significant potency. Most of its pharmacological properties are similar to those of halothane, although there may be slightly less nausea, vomiting, arrhythmias, and postoperative shivering than observed with halothane. High concentrations of enflurane, however, are more likely to produce convulsions and circulatory depression. Enflurane also relaxes the uterus and, thus, should not be used as an anesthetic during labor. Metabolism via CYP2E1 accounts for 2% of an inhaled dose and includes transformation to the fluoride ion and fluoromethoxydifluoroacetic acid. During recovery, enflurane leaves the fatty tissues rapidly and, therefore, is not available for a prolonged period of time for significant metabolism to proceed.

Technology Process of Enflurane

There total 3 articles about Enflurane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

→ enflurane (13838-16-9,22194-21-4,22194-22-5)

Guidance literature:

Reference yield:

(2-chloro-1,1,2-trifluoroethyl)dichloromethylether (428-96-6) → enflurane (13838-16-9,22194-21-4,22194-22-5)

Guidance literature:

With hydrogen fluoride; antimonypentachloride; at 0 ℃;

DOI:10.1021/jm00276a008

Reference yield:

2-chloroethyl methyl ether (627-42-9) → 2-Chloro-1,1,2-trifluoroethyl fluoromethyl ether (5073-63-2) + enflurane (13838-16-9,22194-21-4,22194-22-5) + 2-Chloro-1,2-difluoroethyl fluoromethyl ether + 2-Chloro-1,2-difluoroethyl difluoromethyl ether

Guidance literature:

With potassium tetrafluorocobaltate; at 250 ℃; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0022-1139(96)03549-X

upstream raw materials:

(2-chloro-1,1,2-trifluoroethyl)dichloromethylether

2-chloroethyl methyl ether

Downstream raw materials:

(R)-(-)-Enfluran

(+)-(S)-enflurane

Refernces

• 1、 Coe, Paul L.,Rowbotham, Roger A.,Tatlow, John Colin. "Chloropolyfluoro-derivatives of ethyl methyl ether". . p. 9 - 12. Retrieved 1997.
• 2、 -. "Process for adjusting the halogen content of halogenated aliphatic ethers". . . Retrieved 2008/06/13.