Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:12 UTC |
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Update Date | 2014-12-24 20:25:54 UTC |
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Accession Number | T3D2962 |
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Identification |
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Common Name | Methoxyflurane |
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Class | Small Molecule |
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Description | An inhalation anesthetic. Currently, methoxyflurane is rarely used for surgical, obstetric, or dental anesthesia. If so employed, it should be administered with nitrous oxide to achieve a relatively light level of anesthesia, and a neuromuscular blocking agent given concurrently to obtain the desired degree of muscular relaxation. (From AMA Drug Evaluations Annual, 1994, p180) |
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Compound Type | - Anesthetic, Inhalation
- Drug
- Ether
- Lachrymator
- Metabolite
- Organic Compound
- Organochloride
- Organofluoride
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | Methoflurane | Methoxiflurane | Methoxifluranum | Methoxyfluoran | Methoxyfluorane | Methoxyfluran | Methoxyfluranum | Methyl 1,1-difluoro-2,2-dichloroethyl ether | Metossiflurano | Metoxfluran | Metoxifluran | Metoxiflurano | Penthrane |
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Chemical Formula | C3H4Cl2F2O |
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Average Molecular Mass | 164.966 g/mol |
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Monoisotopic Mass | 163.961 g/mol |
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CAS Registry Number | 76-38-0 |
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IUPAC Name | 2,2-dichloro-1,1-difluoro-1-methoxyethane |
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Traditional Name | methoxyflurane |
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SMILES | COC(F)(F)C(Cl)Cl |
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InChI Identifier | InChI=1S/C3H4Cl2F2O/c1-8-3(6,7)2(4)5/h2H,1H3 |
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InChI Key | InChIKey=RFKMCNOHBTXSMU-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Ethers |
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Direct Parent | Dialkyl ethers |
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Alternative Parents | |
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Substituents | - Dialkyl ether
- Hydrocarbon derivative
- Organofluoride
- Organochloride
- Organohalogen compound
- Alkyl halide
- Alkyl fluoride
- Alkyl chloride
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Liquid |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | -35°C | Boiling Point | 105°C | Solubility | 2.83E+004 mg/L (at 37°C) | LogP | 2.21 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-9300000000-2b014e075c584d7d00e8 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-0900000000-31aa3948ca3dc3167617 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-286e18d415df7a2ecce2 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-1900000000-a0e34ecec1f1427e9b36 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-5826e7c4a8fc419eecaa | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dl-0900000000-38434e069c688783ff1c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03ec-0900000000-f972b01b9fa825e56f30 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-c2759436c4d32d8702ce | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-f4a5c266171cbb5ab6fb | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-8900000000-fbf5bd1b60bed06b6fa7 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-9100000000-f375f8e7cda89aed201f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01q9-9500000000-8e6af6b8d5c2905c7078 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03di-0900000000-d7dee0ac770c9b80f6d9 | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | splash10-001i-9100000000-e9387eb71a01da84865e | JSpectraViewer | MoNA | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Oral |
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Mechanism of Toxicity | Methoxyflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Methoxyflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. It also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Methoxyflurane also binds to the GABA receptor, the large conductance Ca2+ activated potassium channel, the glutamate receptor and the glycine receptor. |
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Metabolism | Hepatic. |
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Toxicity Values | LD50: 3600 mg/kg (Oral, Rat) (1) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For use in the induction and maintenance of general anesthesia |
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Minimum Risk Level | Not Available |
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Health Effects | Detrimental effects on the kidneys. [Wikipedia] |
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Symptoms | Symptoms of overexposure include eye irritation, CNS depression, analgesia, anesthesia, seizures, respiratory depression, and liver and kidney damage. |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01028 |
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HMDB ID | HMDB15162 |
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PubChem Compound ID | 4116 |
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ChEMBL ID | CHEMBL1341 |
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ChemSpider ID | 3973 |
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KEGG ID | C07517 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 384208 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Methoxyflurane |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Methoxyflurane |
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References |
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Synthesis Reference | Not Available |
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MSDS | Link |
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General References | - Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
- Drugs.com [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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