Halogenated ether compounds and methods of inducing anesthesia

Abstract

A method of inducing anesthesia in a subject is provided. In some embodiments, the method provides administering to the subject via the respiratory system or via injection, an effective amount of a compound or a mixture of compounds selected from the group consisting of methyl-ethyl ethers, methyl-isopropyl ethers, and methyl-propyl ethers.

1 . A compound for use in a method for inducing anesthesia in a subject, which method comprises administering to the subject via the respiratory system or via injection, an effective amount of ethane, 1-bromo-1,1,2-trifluoro-2-(trifluoromethoxy)-(CAS #2356-55-0). 
     
     
         2 . The compound of  claim 1 , wherein the subject is a mammal. 
     
     
         3 . The compound of  claim 2 , wherein the subject is a human. 
     
     
         4 . The compound of  claim 1 , wherein the step of inducing anesthesia includes inducing a state selected from the group consisting of analgesia, tranquilization, sedation, amnesia, a hypnotic state, and a state of insensitivity to noxious stimulation. 
     
     
         5 . A method for inducing anesthesia in a subject, comprising administering to the subject via the respiratory system or via injection, an effective amount of ethane, 1-bromo-1,1,2-trifluoro-2-(trifluoromethoxy)-(CAS #2356-55-0). 
     
     
         6 . The method of  claim 5 , wherein the subject is a mammal. 
     
     
         7 . The method of  claim 6 , wherein the subject is a human. 
     
     
         8 . The method of  claim 5 , wherein the step of inducing anesthesia includes inducing a state selected from the group consisting of analgesia, tranquilization, sedation, amnesia, a hypnotic state, and a state of insensitivity to noxious stimulation. 
     
     
         9 . A method for inducing anesthesia in a subject, the method comprising administering to the subject via the respiratory system or via injection, an effective amount of a compound or a mixture of compounds selected from the group consisting of a halogenated methyl-ethyl ether, a halogenated methyl-isopropyl ether, and a halogenated methyl-propyl ether,
 wherein the halogenated methyl-ethyl ether is selected from the group consisting of: Ethane, 1-(chlorodifluoromethoxy)-1,1,2,2,2-pentafluoro-(CAS #276640-96-1); Ethane, 2-bromo-1,1,1-trifluoro-2-(trifluoromethoxy)-(CAS #84011-04-1); Ethane, 1-bromo-1,2,2-trifluoro-1-(trifluoromethoxy)-(CAS #885275-60-5); Ethane, 2-bromo-1,1,2-trifluoro-1-(trifluoromethoxy)-(CAS #84011-03-0); Ethane, 1-bromo-1,1,2-trifluoro-2-(trifluoromethoxy)-(CAS #2356-55-0); Ethane, 2-chloro-1,1,2-trifluoro-1-(trifluoromethoxy)-(CAS #879885-11-7); Ethane, 2-chloro-1,1,1-trifluoro-2-(trifluoromethoxy)-(CAS #94720-92-0); Ethane, 1-chloro-1,1,2-trifluoro-2-(trifluoromethoxy)-(CAS #2356-59-4); Ethane, 1-chloro-1,1-difluoro-2-(trifluoromethoxy)-(CAS #1645-80-3); Ethane, 1-chloro-1,2-difluoro-2-(trifluoromethoxy)-, (R*,S*)-(9CI) (CAS #84011-29-0); Ethane, 1-chloro-1,2-difluoro-2-(trifluoromethoxy)-, (R*,R*)-(9CI) (CAS #84011-28-9); Ethane, 1-chloro-1,2-difluoro-2-(trifluoromethoxy)-(CAS #54362-39-9); Ethane, 1-chloro-2,2-difluoro-1-(trifluoromethoxy)-(CAS #33445-33-9); and mixtures thereof;   wherein the halogenated methyl-isopropyl ether is selected from the group consisting of: Propane, 1-chloro-1,1,2,3,3,3-hexafluoro-2-(trifluoromethoxy)-(CAS #41255-97-4); Propane, 1,1,1,2,3,3,3-heptafluoro-2-(trifluoromethoxy)-(CAS #60901-74-8); Propane, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethoxy)-(CAS #162401-05-0); Propane, 2-(difluoromethoxy)-1,1,1,2,3,3-hexafluoro-(CAS #233258-12-3); and mixtures thereof; and   wherein the halogenated methyl-propyl ether is selected from the group consisting of: Propane, 1,1,2,2,3,3-hexafluoro-1-methoxy-(CAS #160620-20-2); Propane, 1,1,1,2,2,3-hexafluoro-3-methoxy-(CAS #123202-00-6); Propane, 1,1,1,2,3,3-hexafluoro-3-(fluoromethoxy)-(CAS #60598-14-3); Propane, 3-(difluoromethoxy)-1,1,1,2,2-pentafluoro-(CAS #56860-81-2); Propane, 1,1,1,2,2-pentafluoro-3-(fluoromethoxy)-(CAS #1515-13-5); and mixtures thereof.   
     
     
         10 . The method of  claim 9 , wherein the compound potentiates GABA A  receptors, but does not inhibit NMDA receptors. 
     
     
         11 . The method of  claim 9  or  10 , wherein the subject is a mammal, and preferably is a human. 
     
     
         12 . A compound for use in a method for inducing anesthesia in a subject, which method comprises administering to the subject via the respiratory system or via injection, an effective amount of a compound or a mixture of compounds selected from the group consisting of a halogenated methyl-ethyl ether, a halogenated methyl-isopropyl ether, and a halogenated methyl-propyl ether,
 wherein the halogenated methyl-ethyl ether is selected from the group consisting of: Ethane, 1-(chlorodifluoromethoxy)-1,1,2,2,2-pentafluoro-(CAS #276640-96-1); Ethane, 2-bromo-1,1,1-trifluoro-2-(trifluoromethoxy)-(CAS #84011-04-1); Ethane, 1-bromo-1,2,2-trifluoro-1-(trifluoromethoxy)-(CAS #885275-60-5); Ethane, 2-bromo-1,1,2-trifluoro-1-(trifluoromethoxy)-(CAS #84011-03-0); Ethane, 1-bromo-1,1,2-trifluoro-2-(trifluoromethoxy)-(CAS #2356-55-0); Ethane, 2-chloro-1,1,2-trifluoro-1-(trifluoromethoxy)-(CAS #879885-11-7); Ethane, 2-chloro-1,1,1-trifluoro-2-(trifluoromethoxy)-(CAS #94720-92-0); Ethane, 1-chloro-1,1,2-trifluoro-2-(trifluoromethoxy)-(CAS #2356-59-4); Ethane, 1-chloro-1,1-difluoro-2-(trifluoromethoxy)-(CAS #1645-80-3); Ethane, 1-chloro-1,2-difluoro-2-(trifluoromethoxy)-, (R*,S*)-(9CI) (CAS #84011-29-0); Ethane, 1-chloro-1,2-difluoro-2-(trifluoromethoxy)-, (R*,R*)-(9CI) (CAS #84011-28-9); Ethane, 1-chloro-1,2-difluoro-2-(trifluoromethoxy)-(CAS #54362-39-9); Ethane, 1-chloro-2,2-difluoro-1-(trifluoromethoxy)-(CAS #33445-33-9); and mixtures thereof;   wherein the halogenated methyl-isopropyl ether is selected from the group consisting of: Propane, 1-chloro-1,1,2,3,3,3-hexafluoro-2-(trifluoromethoxy)-(CAS #41255-97-4); Propane, 1,1,1,2,3,3,3-heptafluoro-2-(trifluoromethoxy)-(CAS #60901-74-8); Propane, 1,1,1,3,3,3-hexafluoro-2-(trifluoromethoxy)-(CAS #162401-05-0); Propane, 2-(difluoromethoxy)-1,1,1,2,3,3-hexafluoro-(CAS #233258-12-3); and mixtures thereof; and   wherein the halogenated methyl-propyl ether is selected from the group consisting of: Propane, 1,1,2,2,3,3-hexafluoro-1-methoxy-(CAS #160620-20-2); Propane, 1,1,1,2,2,3-hexafluoro-3-methoxy-(CAS #123202-00-6); Propane, 1,1,1,2,3,3-hexafluoro-3-(fluoromethoxy)-(CAS #60598-14-3); Propane, 3-(difluoromethoxy)-1,1,1,2,2-pentafluoro-(CAS #56860-81-2); Propane, 1,1,1,2,2-pentafluoro-3-(fluoromethoxy)-(CAS #1515-13-5); and mixtures thereof.   
     
     
         13 . The compound of  claim 12 , wherein the compound potentiates GABA A  receptors, but does not inhibit NMDA receptors. 
     
     
         14 . The compound of  claim 12 , wherein the subject is a mammal, and preferably is a human. 
     
     
         15 . The compound of  claim 12 , wherein the compound has a molar water solubility of less than about 11 mM, and preferably less than about 5.7 mM. 
     
     
         16 . The compound of  claim 12 , wherein the compound has a molar water solubility of more than about 2.4 mM.