APPLIED CHEMISTRY INHALATION AGENTS

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APPLIED CHEMISTRY INHALATION AGENTS
Mark Welliver CRNA MS
Mark Welliver Slide 2006
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Outline

• IUPAC nomenclature rules
• Functional groups
• Alkanes, Alkene, Alkynes
• Ethers
• Carboxyls
• Alcohols
• Aldehydes
• Amines
• Ketones

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Inhaled Anesthetic Agents
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Volatile Anesthetics Halogenated
Alkane Halothane (Fluothane) 2-bromo-2-chloro-1,
1,1-trifluoro-ethane Halogenated Hydrocarbons
(methyl ethyl ethers) Enflurane (Ethrane)
2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether Isoflurane (Forane)
1-chloro-2,2,2-trifluoroethyl difluoromethyl
ether Desflurane (Suprane) 1,2,2,2-tetrafluoro
ethyl difluoromethyl ether Sevoflurane
(Ultane) fluromethyl 1,1,1,3,3,3,-hexa-fluoro- i
sopropyl ether or fluoromethyl
2,2,2-trifluoro-1-(trifluoromethyl) ethyl
ether Non-Volatile Anesthetic Inorganic
Gas Nitrous Oxide-N2O
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Chemical Structure of Inhalation Agents
H
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IUPAC Nomenclature

• The IUPAC name for an organic compound contains
  these two parts
• 1) a root indicating how many carbon atoms are in
  the longest continuous chain of carbon atoms
• 2) a prefix and/or a suffix to indicate the
  family or functional group to which the compound
  belongs.

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Root Names
memorize!
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Functional Groups
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Hydrocarbons

• Volatile anesthetics are hydrocarbons
• And they contain halogens, F-,Cl-, Br-
• They are Halogenated hydrocarbons
• Two main categories
• 1) Alkanes
• 2) Ethers

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Alkanes

• Alkanes are single-chained hydrocarbons
• Alkenes are double bonded C C
• Alkynes are triple bonded C C
• Halogenated Alkane- Halogens added F,CL, Br

C-C
ethane
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Nomenclature-Alkanes

• The smallest alkane to exhibit isomerism is
  butane with 2 isomers

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• Isomer A has the four carbons in a chain and so
  is butane

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• Isomer B has three carbons in a chain and the
  fourth carbon branching off the centre. To name
  compounds such as this one, with branches, the
  IUPAC system
• chooses a root name to indicate the longest
  continuous chain of carbons, in this case prop
  for the three carbons.
• name the branch.

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• Name the Branch
• - using the root name for the longest continuous
  chain of
• carbons in the branch (in this case meth for
  the one
• carbon)
• -followed by -yl to indicate that this number of
  carbons is
• in a branch.
• put the three parts of the name (branch root
  family)
• together to form the compounds name, with the
  branch
• names prefixing the root, and the family name
  taking its
• usual form.
• Following these steps, compound B is named
• methylpropane

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Alkane Nomenclature

• 1.) Count the longest carbon chain
• If the carbon chain is
• 1 carbon named "methane"
• 2 carbons named "ethane"
• 3 carbons named "propane"
• 4 carbons named "butane"
• 5 carbons named "pentane"
• 6 carbons named "hexane"
• 7 carbons named "heptane"
• 8 carbons named "octane"
• 9 carbons named "nonane"
• 10 carbons named "decane"

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Alkane Nomenclature

• 2.) Number the carbon chain, starting with the
  end closest to the substituent. Always try to get
  the lowest number possible.
• If there are two substituents, name the carbon
  chain so that it has the lowest possible number

C
C
1
3
5
C-C-C-C-C-C
2
4
6
6
5
4
3
2
1
Would this compound be numbered from the left or
right? The answer is that it would be answered
from the right. If the molecule was named from
the  left, you would have substituents on carbons
3 and 5. Numbering from the right, the
subsituents are on carbons 2 and 4.
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Alkane Nomenclature

• 3.) Name and number the substituent keep
  substituents alphabetical

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Alkane Nomenclature

• 3.) Name and number the substituent

2,4 di methyl hexane
2 methyl hexane
2,3 di methyl hexane
3 ethyl, 2,4 di methyl hexane
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Name the following
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Halogenated Alkanes

• Halogens added F,Cl, Br
• Halothane
• The only halogenated alkane anesthetic in use
• Name the above compound
• 2-bromo-2-chloro-1,1,1-trifluoro-ethane

F
Cl
-
-
Br-C-C-F
-
-
F
H
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Halogenated Alkanes

• Halogens added F,Cl, Br
• Halothane
• The only halogenated alkane anesthetic in use,
  rare

F
Cl
-
-
Br-C-C-F
-
-
F
H
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Alkane vs Ether

• The C2H5 group is known as an ethyl- group.
• However, the C2H5O group is known as the ethoxy-
  group. Below is a table with the most common oxy-
  groups you'll find.

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Ethers R-O-R1

• Two types of ethers
• Cyclic
• Acyclic

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Ethers

• Two groups acyclic cyclic
  (acyclic focus)
• Ethers are R-O-R'. The RO- is called the alkoxy
  group
• C-O-C basic ether building block
• C-O -C

Alkane group
Alkoxy group
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Nomenclature Ethers

• C-O-C methoxy methane/ dimethyl ether
• C-O-C-C methoxy ethane/ ethyl methyl ether
• C-O-C-C-C methoxy propane/methyl propyl ether
• Alphabetical or by size (smaller to longer)
• Usually longest chain takes name

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Nomenclature Ethers

• H3C-O-C2H5 / C-O-C-C
• Naming substituents in ethers
• The longest parent chain is the ethane group.
  Thus the methyoxy- becomes the substituent group.
  Hence, the name of this molecule is
  methyoxyethane or methoxy ethane or
  ethyl methyl ether or methyl
  ethyl ether

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Nomenclature- Halogenated Inhalation Ethers

• Methyl (one carbon) ethyl (two carbon) ethers
  (R-O-R)
• C -C-O-C

1
2
1
Ethyl group
Methyl group
R-O-R ether
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Enflurane (Ethrane)
F
Cl
F
-
-
-

• -C-C-O-C-

H
H
1
2
1
-
-
-
F
F
F
2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether 1,1difluro methoxy 1,1,2, trifluro 2 chloro
ethane
Enflurane (Ethrane)
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Nomenclature- Inhalation Ethers

• Methyl (one carbon) ethyl (two carbon) ethers
  (R-O-R)
• Isoflurane (Forane) 1-chloro-2,2,2-trifluoroethyl
  difluoromethyl ether
• C -C-O-C

1
2
1
Ethyl group
Methyl group
R-O-R ether
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Isoflurane / Flurane
Cl
F
F
-
-
-

• -C-C-O-C-

H
F
1
2
1
-
-
-
F
H
F
1-chloro-2,2,2-tetrafluoroethyl difluoromethyl
ether 1,1difluro methoxy 1 chloro- 2,2,2,
trifluro ethane
Isoflurane (Forane)
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Desflurane / Suprane
F
F
F
-
-
-

• -C-C-O-C-

1
H
2
1
F
-
-
-
F
H
F
1,2,2,2 tetrafluro ethyl difluoro methyl
ether 1,1difluro methoxy 1,2,2,2, tetrafluro
ethane
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Sevoflurane / Ultane
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F
-
F
-F
F-
C
-

• -C-O-C-

H
H
-
-
-C-
H
F
F
-
F
fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)
ethyl ether fluromethyl 1,1,1,3,3,3, hexafluoro
isopropyl ether 1, fluoro methoxy 1,1,1 trifluoro
methyl 2,2,2 trifluoro ethane
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Volatile Anesthetics Halogenated
Alkane Halothane (Fluothane) 2-bromo-2-chloro-1,1
,1-trifluoro-ethane Enflurane (Ethrane)
2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether Isoflurane (Forane) 1-chloro-2,2,2-triflu
oroethyl difluoromethyl ether Desflurane
(Suprane) 1,2,2,2-tetrafluoroethyl difluoromethyl
ether Sevoflurane (Ultane) fluromethyl
1,1,1,3,3,3,-hexa-fluoro-isopropyl ether or
fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)
ethyl ether Non-Volatile Anesthetic Inorganic
Gas Nitrous Oxide-N2O
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Ethers

• - O - C2H5
• The parent chain will be the cyclohexane group.
  We have an ethyoxy group, so we get a
  ethyoxycyclohexane.

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