View source for Isoflurane

{{Short description|Inhalational anesthetic}}
{{Use dmy dates|date=October 2025}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443883276
| image = Isoflurane.svg
| image_class = skin-invert-image
| width = 150
| alt = 
| image2 = Isoflurane-3D-vdW.png
| image_class2 = bg-transparent
| width2 = 150
| alt2 = 
| caption =

<!-- Clinical data -->
| pronounce = 
| tradename = Forane, others
| Drugs.com = {{Drugs.com|pro|isoflurane}}
| MedlinePlus = 
| DailyMedID = Isoflurane
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Isoflurane Use During Pregnancy | website=Drugs.com | date=2 September 2020 | url=https://www.drugs.com/pregnancy/isoflurane.html | access-date=9 September 2020}}</ref>
| pregnancy_category = 
| routes_of_administration = [[Inhalation administration|Respiratory]]
| class = [[Inhalational anesthetic]]
| ATCvet=
| ATC_prefix=N01
| ATC_suffix=AB06
| ATC_supplemental={{ATCvet|N01|AB06}}

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment = 
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment = 
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment = 
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment = 
| legal_UK = POM
| legal_UK_comment = <ref name="Isoflurane SmPC">{{cite web | title=Isoflurane 100% Inhalation Vapour, Liquid - Summary of Product Characteristics (SmPC) | website=(emc) | date=29 October 2019 | url=https://www.medicines.org.uk/emc/product/9800/smpc | access-date=9 September 2020}}</ref>
| legal_US = Rx-only
| legal_US_comment = <ref name="Forane FDA label">{{cite web | title=Forane- isoflurane inhalant | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3d30eb8d-a62e-475f-926b-78ba63bee9c8 | access-date=11 February 2022}}</ref><ref name="Terrell FDA label">{{cite web | title=Terrell- isoflurane liquid | website=DailyMed | date=9 February 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=dbeb646f-dc6c-40f2-803c-68858d6ac080 | access-date=4 October 2025}}</ref>
| legal_EU = 
| legal_EU_comment = 
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment = 
| legal_status = <!-- For countries not listed above -->

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = {{val|1.14|0.35|u=minutes}} to 50% steady-state.<ref name=Kinetics>{{cite journal | vauthors = Freiermuth D, Mets B, Bolliger D, Reuthebuch O, Doebele T, Scholz M, Gregor M, Haschke M, Seeberger MD, Fassl J | title = Sevoflurane and Isoflurane-Pharmacokinetics, Hemodynamic Stability, and Cardioprotective Effects During Cardiopulmonary Bypass | journal = Journal of Cardiothoracic and Vascular Anesthesia | volume = 30 | issue = 6 | pages = 1494–1501 | date = December 2016 | pmid = 27692704 | doi = 10.1053/j.jvca.2016.07.011 }}</ref>
| elimination_half-life=~10 minutes<ref name=Kinetics />
| duration_of_action = 
| excretion =

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 26675-46-7
| CAS_supplemental = 
| PubChem = 3763
| IUPHAR_ligand = 2505
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00753
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3631
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CYS9AKD70P
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00545
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6015
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1256
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms =

<!-- Chemical and physical data -->
| IUPAC_name=2-chloro-2-difluoromethoxy-1,1,1-trifluoroethane
| C=3 | H=2 | Cl=1 | F=5 | O=1
| SMILES = FC(F)(F)C(Cl)OC(F)F
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H2ClF5O/c4-1(3(7,8)9)10-2(5)6/h1-2H
| StdInChI_comment = 
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PIWKPBJCKXDKJR-UHFFFAOYSA-N
| density = 1.496
| density_notes =<ref name="PubChem">{{Cite web | work = PubChem | publisher = U.S. National Library of Medicine |title=Isoflurane |url=https://pubchem.ncbi.nlm.nih.gov/compound/3763 |access-date=2022-04-07 |language=en}}</ref> 
| melting_point = 
| melting_high = 
| melting_notes = 
| boiling_point = 48.5
| boiling_notes = <ref name="PubChem" />
| solubility=13.5 mM (at {{convert|25|C|F}})<ref>{{cite journal | vauthors = Seto T, Mashimo T, Yoshiya I, Kanashiro M, Taniguchi Y | title = The solubility of volatile anaesthetics in water at 25.0 degrees C using 19F NMR spectroscopy | journal = Journal of Pharmaceutical and Biomedical Analysis | volume = 10 | issue = 1 | pages = 1–7 | date = January 1992 | pmid = 1391078 | doi = 10.1016/0731-7085(92)80003-6 }}</ref>
| sol_units =
| specific_rotation = 
}}

'''Isoflurane''', sold under the brand name '''Forane''' among others, is a [[halogenated ether]] used as a [[general anesthetic]].<ref name="Forane FDA label" /><ref>{{cite book | vauthors = Aglio LS, Lekowski RW, Urman RD |title=Essential Clinical Anesthesia Review: Keywords, Questions and Answers for the Boards |date=2015 |publisher=Cambridge University Press |isbn=978-1-107-68130-9 |page=115 |url=https://books.google.com/books?id=VJzWBQAAQBAJ&pg=PA115 |language=en|url-status=live |archive-url=https://web.archive.org/web/20161220113456/https://books.google.ca/books?id=VJzWBQAAQBAJ&pg=PA115 |archive-date=2016-12-20}}</ref> It can be used to start or maintain [[anesthesia]]; however, other medications are often used to start anesthesia, due to airway irritation with isoflurane.<ref name="Isoflurane SmPC" /><ref>{{cite book| vauthors = Kliegman R, Stanton B, St Geme J, Schor NF |title=Nelson Textbook of Pediatrics|date=2015|publisher=Elsevier Health Sciences|isbn=978-0-323-26352-8|page=420|edition=20|url=https://books.google.com/books?id=P9piCAAAQBAJ&pg=PA420|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220113801/https://books.google.ca/books?id=P9piCAAAQBAJ&pg=PA420|archive-date=2016-12-20}}</ref> Isoflurane is a [[inhalational anesthetic]] given via [[Inhalation administration|inhalation]].<ref name="Forane FDA label" />

Isoflurane was approved for medical use in the United States in 1979.<ref name="Forane FDA label" /><ref>{{cite web | title=Forane: FDA-Approved Drugs | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=017624 | access-date=11 February 2022}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO24th">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines, 2025: WHO Model List of Essential Medicines, 24th list | year = 2025 | hdl = 10665/382243 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl-access = free | doi = 10.2471/B09474 | doi-access = free | id = License: CC BY-NC-SA 3.0 IGO }}</ref>

==Medical uses==
Isoflurane is [[indicated]] for induction and maintenance of general anesthesia.<ref name="Forane FDA label" />

Isoflurane is always administered in conjunction with [[air]] or pure [[oxygen]]. Often, [[nitrous oxide]] is also used. Although its physical properties imply that anaesthesia can be induced more rapidly than with [[halothane]],<ref name="NiedermeyerSilva2005">{{cite book| vauthors = Niedermeyer E, da Silva FH |title=Electroencephalography: Basic Principles, Clinical Applications, and Related Fields|url=https://books.google.com/books?id=tndqYGPHQdEC&pg=PA1156|year=2005|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-5126-1|page=1156|url-status=live|archive-url=https://web.archive.org/web/20160509001417/https://books.google.com/books?id=tndqYGPHQdEC&pg=PA1156|archive-date=2016-05-09}}</ref> its pungency can irritate the respiratory system, negating any possible advantage conferred by its physical properties. Thus, it is mostly used in general anesthesia as a maintenance agent after induction of general anesthesia with an intravenous agent such as [[thiopentone]] or [[propofol]].<ref>{{cite journal |vauthors=Pauca AL, Dripps RD |title=Clinical experience with isoflurane (Forane): preliminary communication |journal=British Journal of Anaesthesia |volume=45 |issue=7 |pages=697–703 |date=July 1973 |pmid=4730162 |doi=10.1093/bja/45.7.697 |doi-access=free}}</ref><ref>{{cite journal |vauthors=Chen Z |title = The effects of isoflurane and propofol on intraoperative neurophysiological monitoring during spinal surgery |journal=Journal of Clinical Monitoring and Computing |volume=18 | issue=4 |pages=303–308 |date=August 2004 |pmid=15779842 |doi=10.1007/s10877-005-5097-5 |s2cid=195331061}}</ref><ref name = NBK532957>{{cite web |url=https://www.ncbi.nlm.nih.gov/books/NBK532957/ |pmid=30422552 |year=2022 |vauthors = Hawkley TF, Preston M, Maani CV |title=Isoflurane |publisher=StatPearls}}</ref>

==Mechanism of action==
Similar to many general anesthetics, the exact mechanism of the action [[Theories of general anaesthetic action|has not been clearly delineated]].<ref>{{cite magazine |url=https://www.scientificamerican.com/article/how-does-anesthesia-work/ |title=How does anesthesia work? |date=February 7, 2005 |magazine=[[Scientific American]] |url-status=live |archive-url = https://web.archive.org/web/20160529012227/http://www.scientificamerican.com/article/how-does-anesthesia-work/ |archive-date=May 29, 2016 }}</ref> Isoflurane reduces pain sensitivity ([[analgesia]]) and relaxes muscles. Isoflurane likely binds to [[GABA receptor|GABA]], [[Glutamate receptor|glutamate]] and [[Glycine receptor|glycine]] receptors, but has different effects on each receptor. Isoflurane acts as a [[positive allosteric modulator]] of the [[GABAA receptor|GABA<sub>A</sub> receptor]] in electrophysiology studies of neurons and recombinant receptors.<ref>{{cite journal |vauthors=Jones MV, Brooks PA, Harrison NL |title=Enhancement of gamma-aminobutyric acid-activated Cl-currents in cultured rat hippocampal neurones by three volatile anaesthetics |journal=The Journal of Physiology |volume=449 |pages=279–293 |date=April 1992 |pmid=1326046 |pmc=1176079 |doi=10.1113/jphysiol.1992.sp019086}}</ref><ref>{{cite journal |vauthors=Jenkins A, Franks NP, Lieb WR | title=Effects of temperature and volatile anesthetics on GABA(A) receptors |journal=Anesthesiology |volume=90 |issue=2 |pages=484–491 |date=February 1999 |pmid=9952156 |doi=10.1097/00000542-199902000-00024 |doi-access=free}}</ref><ref>{{cite journal |vauthors=Lin LH, Chen LL, Zirrolli JA, Harris RA |title=General anesthetics potentiate gamma-aminobutyric acid actions on gamma-aminobutyric acidA receptors expressed by Xenopus oocytes: lack of involvement of intracellular calcium |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=263 |issue=2 |pages=569–578 | date=November 1992 |doi=10.1016/S0022-3565(25)10387-X |pmid=1331405}}</ref><ref>{{cite journal |vauthors=Krasowski MD, Harrison NL |title=The actions of ether, alcohol and alkane general anaesthetics on GABAA and glycine receptors and the effects of TM2 and TM3 mutations |journal=British Journal of Pharmacology |volume=129 |issue=4 | pages=731–743 |date=February 2000 |pmid=10683198 |pmc=1571881 |doi=10.1038/sj.bjp.0703087}}</ref> It potentiates glycine receptor activity, which decreases motor function.<ref>{{cite journal |vauthors=Grasshoff C, Antkowiak B |title=Effects of isoflurane and enflurane on GABAA and glycine receptors contribute equally to depressant actions on spinal ventral horn neurones in rats |journal=British Journal of Anaesthesia |volume=97 |issue=5 |pages=687–694 |date=November 2006 |pmid=16973644 |doi=10.1093/bja/ael239 |s2cid=14269792 |doi-access=free}}</ref> It inhibits receptor activity in the [[NMDA]] glutamate receptor subtypes. Isoflurane inhibits conduction in activated [[potassium channel]]s.<ref>{{cite journal | vauthors = Buljubasic N, Rusch NJ, Marijic J, Kampine JP, Bosnjak ZJ |title= Effects of halothane and isoflurane on calcium and potassium channel currents in canine coronary arterial cells |journal=Anesthesiology |volume=76 |issue=6 |pages=990–998 |date=June 1992 |pmid=1318010 |doi=10.1097/00000542-199206000-00020 |doi-access=free}}</ref> Isoflurane also affects intracellular molecules. It inhibits [[plasma membrane]] [[calcium ATPase]]s (PMCAs) which affects membrane fluidity by hindering the flow of {{chem2|Ca(2+)}} ([[calcium]] [[ion]]s) out across the membrane, this in turn affects [[neuron]] [[depolarization]].<ref>{{cite journal |vauthors = Franks JJ, Horn JL, Janicki PK, Singh G |title=Halothane, isoflurane, xenon, and nitrous oxide inhibit calcium ATPase pump activity in rat brain synaptic plasma membranes |journal=Anesthesiology |volume=82 |issue=1 |pages=108–117 |date=January 1995 |pmid=7832292 |doi=10.1097/00000542-199501000-00015 |s2cid=26993898 |doi-access=free}}</ref> It binds to the D subunit of [[ATP synthase]] and [[NADH dehydrogenase]].

General anaesthesia with isoflurane reduces plasma [[Endocannabinoid system|endocannabinoid]] [[Anandamide|AEA]] concentrations, and this could be a consequence of [[Stress management|stress reduction]] after [[Unconsciousness|loss of consciousness]].<ref>{{cite journal |vauthors=Weis F, Beiras-Fernandez A, Hauer D, Hornuss C, Sodian R, Kreth S, Briegel J, Schelling G |title=Effect of anaesthesia and cardiopulmonary bypass on blood endocannabinoid concentrations during cardiac surgery |journal=British Journal of Anaesthesia |volume=105 |issue=2 |pages=139–144 |date=August 2010 |pmid=20525978 |doi=10.1093/bja/aeq117 |doi-access=free}}</ref>

==Adverse effects==
Side effects of isoflurane include a [[Hypoventilation|decreased ability to breathe]] (respiratory depression), [[low blood pressure]], and an [[irregular heartbeat]].<ref name="Isoflurane SmPC" />  Isoflurane can cause a sudden decrease in blood pressure due to dose-dependent peripheral vasodilation. This may be specially marked in hypovolemic patients.<ref name = NBK532957/> 

Serious side effects can include [[malignant hyperthermia]] or [[hyperkalemia|high blood potassium]].<ref name="Forane FDA label" /> It should not be used in patients with a history of malignant hyperthermia in either themselves or their family members.<ref name="Isoflurane SmPC" /> 

It is unknown if its use during [[pregnancy]] is safe for the fetus, but use during a [[cesarean section]] appears to be safe.<ref name="Isoflurane SmPC" /><ref name="Forane FDA label" />

Animal studies have raised safety concerns of certain general anesthetics, in particular [[ketamine]] and isoflurane, in young children. The risk of [[neurodegeneration]] was increased in combination of these agents with nitrous oxide and [[benzodiazepines]] such as [[midazolam]].<ref name=Mel2007>{{cite journal | vauthors = Mellon RD, Simone AF, Rappaport BA | title = Use of anesthetic agents in neonates and young children | journal = Anesthesia and Analgesia | volume = 104 | issue = 3 | pages = 509–520 | date = March 2007 | pmid = 17312200 | doi = 10.1213/01.ane.0000255729.96438.b0 | url = http://www.anesthesia-analgesia.org/cgi/content/full/104/3/509 | url-status = live | s2cid = 43818997 | archive-url = https://web.archive.org/web/20090309165832/http://www.anesthesia-analgesia.org/cgi/content/full/104/3/509 | archive-date = 2009-03-09 | doi-access = free }}</ref> Whether these concerns occur in humans is unclear.<ref name=Mel2007/>

===Elderly===
Biophysical studies using [[NMR spectroscopy]] has provided molecular details of how inhaled anesthetics interact with three amino acid residues (G29, A30 and I31) of amyloid beta peptide and induce aggregation.<ref name="Mandal-2009">{{cite journal | vauthors = Mandal et al | title = Isoflurane and desflurane at clinically relevant concentrations induce amyloid b-peptide oligomerization: An NMR study | journal =  Biochemical and Biophysical Research Communications| volume = 379 | pages = 716–720 | date = April 2009 | issue = 3 |  doi = 10.1016/j.bbrc.2008.12.092 | pmid = 19116131 | bibcode = 2009BBRC..379..716M }}</ref> This area is important as "some of the commonly used inhaled anesthetics may cause brain damage that accelerates the onset of Alzheimer's disease".<ref name="Kuehn-2007">{{cite journal | vauthors = Kuehn BM | title = Anesthesia-Alzheimer disease link probed | journal = JAMA | volume = 297 | issue = 16 | page = 1760 | date = April 2007 | pmid = 17456811 | doi = 10.1001/jama.297.16.1760 }}</ref>

==Anesthetic physical properties==
Isoflurane has a [[Minimum alveolar concentration]] (MAC) of 1.15 vol %.  The [[blood/gas partition coefficient]] is 1.4, and the [[oil/gas partition coefficient]] is 98.{{citation needed|date=June 2025}} Its vapor pressure at {{convert|20|C|F}} is {{convert|31.7|kPa|mmHg}}.<ref name="PubChem" />

It is administered as a [[racemic mixture]] of (''R'')- and (''S'')-optical isomers.<ref>{{cite journal | vauthors = Bu W, Pereira LM, Eckenhoff RG, Yuki K | title = Stereoselectivity of isoflurane in adhesion molecule leukocyte function-associated antigen-1 | journal = PLOS ONE | volume = 9 | issue = 5 | article-number = e96649 | date = 2014-05-06 | pmid = 24801074 | pmc = 4011845 | doi = 10.1371/journal.pone.0096649 | doi-access = free | bibcode = 2014PLoSO...996649B }}</ref> It is non-[[Combustibility and flammability|combustible]] but can give off irritable and [[Toxicity|toxic]] fumes when exposed to flame.<ref name="PubChem" />

==History==
Together with [[enflurane]] and [[halothane]], Isoflurane began to replace the flammable [[Diethyl ether|ethers]] used in the pioneer days of [[surgery]]; this shift began in the 1940s to the 1950s.<ref>{{cite journal | vauthors = Terrell RC | title = The invention and development of enflurane, isoflurane, sevoflurane, and desflurane | journal = Anesthesiology | volume = 108 | issue = 3 | pages = 531–533 | date = March 2008 | pmid = 18292690 | doi = 10.1097/ALN.0b013e31816499cc | doi-access = free }}</ref> Its name comes from being a [[structural isomer]] of enflurane, hence they have the same [[empirical formula]].<ref>{{cite journal | vauthors = Calvey TN | title = Isomerism and anaesthetic drugs | journal = Acta Anaesthesiologica Scandinavica. Supplementum | volume = 106 | pages = 83–90 | date = August 1995 | pmid = 8533553 | doi = 10.1111/j.1399-6576.1995.tb04316.x | s2cid = 24183480 }}</ref>

==Environment==
The average lifetime of isoflurane in the atmosphere is 3.2 years, its [[global warming potential]] is 510 (times greater than carbon dioxide) and yearly emissions as of 2015 were 880 tons.<ref>{{cite journal| vauthors = Vollmer MK, Rhee TS, Rigby M, Hofstetter D, Hill M, Schoenenberger F, Reimann S | year = 2015| title = Modern inhalation anesthetics: Potent greenhouse gases in the global atmosphere| journal = Geophysical Research Letters| volume = 42| issue = 5| pages = 1606–1611| doi = 10.1002/2014GL062785|bibcode=2015GeoRL..42.1606V |url=https://www.dora.lib4ri.ch/empa/islandora/object/empa%3A6687 |doi-access=free }}</ref>{{update inline|reason=Need a current number.|date=June 2025}}

== Veterinary use ==
Isoflurane is used for the induction and maintenance of [[general anesthesia]] in horses and dogs.<ref>{{cite web | title=Isosol- isoflurane liquid | website=DailyMed | date=2 February 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b69c2259-d7d8-482d-8443-6279d217da0a | access-date=4 October 2025}}</ref><ref>{{cite web | title=Isospire- isoflurane liquid | website=DailyMed | date=13 December 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=816dc04f-6106-47c8-a7d5-34e2d542b212 | access-date=4 October 2025}}</ref><ref>{{cite web | title=Fluriso- isoflurane liquid | website=DailyMed | date=14 February 2023 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=51d92b9b-1226-4bbe-8d42-fb0bfdffabf3 | access-date=4 October 2025}}</ref><ref>{{cite journal | vauthors = Ludders JW | title = Advantages and guidelines for using isoflurane | journal = The Veterinary Clinics of North America. Small Animal Practice | volume = 22 | issue = 2 | pages = 328–331 | date = March 1992 | pmid = 1585568 | doi = 10.1016/s0195-5616(92)50626-x | doi-access = free }}</ref><ref>{{Cite web |title=Isoflurane-Vet 100% w/w Inhalation vapour, liquid |url=https://www.noahcompendium.co.uk/ |access-date=2022-04-07 |website=www.noahcompendium.co.uk |language=en}}</ref>

== References ==
{{Reflist}}

== External links ==
* {{US patent|3535388}} - 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether
* {{US patent|3535425}} - 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether as an anesthetic agent

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