Methoxyflurane

Base Information

• Chemical Name: Methoxyflurane
• CAS No.: 76-38-0
• Deprecated CAS: 8056-95-9
• Molecular Formula: C3H4 Cl2 F2 O
• Molecular Weight: 164.967
• Hs Code.: 2909191800
• European Community (EC) Number: 200-956-0
• ICSC Number: 1636
• NSC Number: 110432
• UN Number: 1993
• UNII: 30905R8O7B
• DSSTox Substance ID: DTXSID7025556
• Nikkaji Number: J2.405H
• Wikipedia: Methoxyflurane
• Wikidata: Q411594
• NCI Thesaurus Code: C75098
• RXCUI: 6857
• Pharos Ligand ID: JPY3G79FHGWZ
• Metabolomics Workbench ID: 43270
• ChEMBL ID: CHEMBL1341
• Mol file: 76-38-0.mol

Synonyms:Anecotan;Methofluranum;Methoxyflurane;Penthrane;Pentrane

Chemical Property of Methoxyflurane

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 19300mmHg at 25°C
• Melting Point: -36°C
• Refractive Index: 1.386
• Boiling Point: 103 °C
• Flash Point: 63 C
• PSA: 9.23000
• Density: 1.4262
• LogP: 2.02930
• Storage Temp.: -70°C
• Water Solubility.: Miscible with alcohol, acetone, chloroform, ether, fixed oils and benzene. Immiscible with water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 163.9607265
• Heavy Atom Count: 8
• Complexity: 75.7
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99%, ^*data from raw suppliers

MYST3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.
• Hazard Codes: Xi
• Statements: 10
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Waste Anesthetic Gases
• Canonical SMILES: COC(C(Cl)Cl)(F)F
• Recent ClinicalTrials: METHOXYFLURANE or Virtual Reality Headset vs Standard Analgesic Management for the Reduction of Anterior Shoulder Dislocation (HYPNOLUX)
• Recent EU Clinical Trials: Pain relief of methoxyflurane in patients with burns
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: Exposure at high levels could cause unconsciousness.
• Effects of Long Term Exposure: The substance may have effects on the kidneys. This may result in kidney impairment.
• Uses: Methoxyflurane is used as a clinical anesthesia (inhalation). Methoxyflurane is a very potent and highly lipid soluble anesthetic agent. Methoxyflurane causes deep sedation and it has been used as a patient controlled analgesic for painful procedures in children. Methoxyflurane is a significant respiratory depressant. 2,2-Dichloro-1,1-difluoroethyl methyl ether is used as a lipid soluble anesthetic agent. It is a neuromuscular blocking agent given concurrently to get the desired degree of muscular relaxation. Further, it is a powerful analgesic agent.
• Biological Functions: Methoxyflurane (Penthrane) is the most potent inhalational agent available, but its high solubility in tissues limits its use as an induction anesthetic. Its pharmacological properties are similar to those of halothane with some notable exceptions. For example, since methoxyflurane does not depress cardiovascular reflexes, its direct myocardial depressant effect is partially offset by reflex tachycardia, so arterial blood pressure is better maintained. Also, the oxidative metabolism of methoxyflurane results in the production of oxalic acid and fluoride concentrations that approach the threshold of causing renal tubular dysfunction. Concern for nephrotoxicity has greatly restricted the use of methoxyflurane.
• Clinical Use: Methoxyflurane is seldom used because of its propensity to cause renal toxicity. It is the most potent agent, and it has the highest solubility in blood. Induction and recovery would be expected to be slow. Chemically, it is rather unstable, and as much as 50% of an administered dose can be metabolized. Toxic metabolites significantly limit its utility as a general anesthetic.

Technology Process of Methoxyflurane

There total 4 articles about Methoxyflurane 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:

methanol (67-56-1) + 1,1,1-trifluoro-2,2-dichloroethane (306-83-2) → methoxyflurane (76-38-0)

Guidance literature:

1,1,1-trifluoro-2,2-dichloroethane; With tetramethyl ammoniumhydroxide; In methanol; at 25 ℃;

methanol; at 120 ℃; for 0.0166667h; Reagent/catalyst; Temperature; Solvent;

Reference yield:

methanol (67-56-1) + 1,1'-dichloro-2,2'-difluoroethene (79-35-6) → methoxyflurane (76-38-0)

Guidance literature:

With potassium hydroxide;

DOI:10.1021/ja01146a519

Reference yield:

1,1'-dichloro-2,2'-difluoroethene (79-35-6) + sodium methylate (124-41-4) → methoxyflurane (76-38-0)

Guidance literature:

unter Eiskuehlung;

DOI:10.1021/ja01181a526

upstream raw materials:

methanol

1,1'-dichloro-2,2'-difluoroethene

sodium methylate

1,1,1-trifluoro-2,2-dichloroethane

Downstream raw materials:

methylene chloride

Methyl fluoride

dichloroacetyl fluoride

2,2,2-Trichloro-1,1-difluoroethyl methyl ether

Refernces

• 1、 -. "PREPARATION OF HALOGENATED ALKOXYETHANE". Page/Page column 36-44. . Retrieved 2021/06/26.