Burke, Chemistry Iv

Front 1

When looking at a structural compound, what does R stand for?
What does X stand for?

Back 1

R = Radical group

X = halogen

Front 2

What is the general formula for a halogen compound?

Back 2

R-X

X can be any halogen atom (chlorine, bromine Iodine)

Front 3

What are all anesthetic agents considered to be?

Back 3

Halogenated compounds

Front 4

Formula for Chloroform

Back 4

CHCl3

Cl
|
H - C - Cl
|
Cl

Front 5

How is a halogen compound formed?

Back 5

A halogen compound (alkyl halide) is formed by replacing one or more hydrogen atoms of an aliphatic (straight-chain) compound with a halogen

Front 6

Most modern inhalation anesthetics have results from ?

Back 6

Halide conversion of alipathic or ether compounds

Front 7

Name some examples of radicals

Back 7

Bicarbonate (HCO3)
Phosphate (PO4)
Sulfate (SO4)
Hydroxyl (OH)
Ammonium (NH4)
Carbonate (CO4)

Front 8

What is a radical?

Back 8

radicals (often referred to as free radicals) are atoms, molecules, or ions with unpaired electrons on an open shell configuration. The unpaired electrons cause them to be highly chemically reactive.

Front 9

Structure of Iodoform
(triiodomethane)

Back 9

I
|
H - C - I
|
I

Front 10

Chloral Hydrate does what?

Back 10

It induces sleep and prevents convulsions

Front 11

What is a Mickey Finn?

Back 11

A Mickey Finn is a "knockout drop". It's a combination of ethyl alcohol and chloral hydrate

Front 12

What is the definition of an alcohol?

Back 12

In chemistry, an alcohol is any organic compound in which a hydroxyl functional group (-OH) is bound to a carbon atom, usually connected to other carbon or hydrogen atoms.

Alcohols are derived from hydrocarbons in which a hydrogen is replaced by an OH group.

Front 13

What is the general formula for an alcohol?

Back 13

R - OH

Front 14

When you replace a hydrogen on methane with an OH, what is the result?
What is the result when you replace a hydrogen on ethane?
On Propane?

Back 14

methyl alcohol

ethyl alcohol

propyl alcohol

Front 15

Name some of the properties of the alcohols

Back 15

Alcohols have a distinctive taste, burn readily, and enter into many chemical reactions.

Front 16

What happens when a primary alcohol is oxidized?

Back 16

When a primary alcohol* is oxidized, an aldehyde is formed:

Methyl alcohol + oxygen  formaldehyde

Front 17

Structure for methyl alcohol

Back 17

H
H────C────OH
H


Methyl alcohol

Front 18

Another name for methyl alcohol?

Back 18

methanol

Front 19

CH3OH

What is it?
name?
Some properties?

Back 19

Methyl alcohol (methanol), CH3OH, is commonly known as wood alcohol. It is used as a solvent in many industrial reactions. Methyl alcohol should never by applied directly to the body nor should the vapors by inhaled because this substance can be absorbed both through the skin and through the respiratory tract. Ingestion of as little as 15 ml of methyl alcohol can cause blindness and 30 ml can cause death.

Front 20

Ethyl Alcohol...give it's compound, properties, etc.

Back 20

Ethyl Alcohol

Ethyl alcohol (ethanol), CH3CH2OH, is known commonly as grain alcohol. In the hospital, the word alcohol means ethyl alcohol. One important property of ethyl alcohol is its ability to denature protein. (Denaturation is the destruction of the usual nature of a substance, as the addition of methanol or acetone to alcohol to render it unfit for drinking, or the change in physical properties of proteins caused by heat or certain chemicals.

Front 21

Ethyl alcohol is widely used in the hospital as an ___?
Discuss.

Back 21

Specifically for protein, disruption of the configuration of a protein, as by heat, change in pH, or other physical or chemical means, resulting in alteration of the physical properties and loss of biological activity of the protein.) Because of this property, ethyl alcohol is widely used as an antiseptic. As an antiseptic, 70 percent is preferred. Seventy percent alcohol is actually a better antiseptic than 100 percent alcohol.

Front 22

Another name for rubbing alcohol?
What are some considerations with it?

Back 22

Isopropyl alcohol (2-propanol) is toxic and should not be taken internally. Since it is not absorbed through the skin, it is commonly used as rubbing alcohol and as an astringent. (Substance that draws together or contracts tissue.)

Front 23

What is a primary alcohol?

Back 23

Primary alcohol - contains one -OH functional group attached to a carbon that has one or no carbon atoms attached to it.

ie, methyl alcohol, ethyl alcohol

Front 24

What is a secondary alcohol

Back 24

A secondary alcohol is one in which the -OH is attached to a carbon atom having two other carbon atoms attached to it.

Front 25

Give an example of a secondary alcohol

Back 25

Isopropyl alcohol is an example of a secondary alcohol. Note that in a secondary alcohol, the functional group is not at the end of the chain.

Front 26

What happens when you oxidize a secondary alcohol?

Back 26

Oxidizing a secondary alcohol* produces a ketone:

Isopropyl alcohol + oxygen  acetone + water

Front 27

What about complex alcohols?

Back 27

Complex alcohols form the basis for such substances as glycol (ethylene glycol), commonly used as antifreeze and poisonous if taken internally. Most alcohols contain some water, but an anhydrous form (deprived of water) is sometimes used to perform a permanent neurolytic block in the treatment of intractable pain.

Front 28

What is an aldehyde?

Back 28

Aldehydes have a functional group that give them their characteristic properties.

Front 29

How are aldehydes formed?

Back 29

As previously mentioned, aldehydes are formed from oxidation (chemically, oxidation consists of an increase of positive charges on an atom or the loss of negative charges. Most biological oxidations are accomplished by the removal of a pair of hydrogen atoms from a molecule.) of primary alcohols.
This process involves removal of two hydrogen atoms from the hydrocarbon. The molecular oxygen that oxidizes the hydrocarbons splits, one atom of oxygen joining the two hydrogens to form water.

Front 30

What happens with the remaining oxygen?

Back 30

The remaining oxygen becomes double-bonded to the carbon atom. Two important aldehydes encountered in medicine are formaldehyde and acetaldehyde.
Both are gases at room temperature, have suffocating odors, and are strong reducing agents (altered by a chemical change involving a gain of electrons).

Front 31

**How is Formaldehyde used?

Back 31

Formaldehyde is used as a tissue preservative.

Front 32

**How is acetylaldehyde used?

Back 32

Acetaldehyde is a breakdown product of ethyl alcohol, which forms the basis of commercial liquors.

Front 33

Is Formaldehyde a liquid, solid, gas??? Discuss it and it's relationship to formalin.

Back 33

Formaldehyde is a colorless gas with a very sharp odor.
It is used in the laboratory as a water solution containing about 40% formaldehyde.
The 40 % solution, commonly known as formalin, is an effective germicide for the disinfection of excreta, rooms, and clothing.

Formalin hardens protein, making it very insoluble in water. It is used in embalming fluids and also as a preservative for biologic specimens.
Formaldehyde solutions should not be used directly on the patient or even in the room with the patient because of irritating fumes.

Front 34

What is gluteraldehyde?

Back 34

Glutaraldehyde is superior to formaldehyde as a sterilizing agent and is gradually replacing it.
Glutaraldehyde is a microcide against all microorganisms, including spores and many viruses.
Glutaraldehyde does not have the disagreeable odor that formaldehyde does, and it is less irritating to the eyes and skin.

Front 35

What is a ketone? How is it formed?

Back 35

Ketones are formed by the oxidation of secondary alcohols.

Front 36

Give an example of a ketone.

Back 36

The best example is acetone.
Acetone is a colorless liquid with a pleasant odor.
An excellent solvent, acetone is particularly useful for removing residual adhesive tape from patient's skin.
Diabetic ketoacidosis is a condition in which the body produces excessive amounts of ketones in the blood and urine

Front 37

What is an ester?

Back 37

Esters are produced by the interaction of an alcohol with an acid.
They are very volatile and have pleasant odors.

Front 38

What is the general formula for an ester?

Back 38

R-C00-R

Front 39

Give some examples of esters

Back 39

Isoamyl nitrite, used in a breakable ampule to treat angina pectoris by relaxing smooth muscles of the CV system, is an example.
The drug is inhaled and enters the bloodstream where it dilates vessels and lowers blood pressure. A whole series of local anesthetic compounds are classed as esters. Most are esters of para-aminobenzoic acid.

Tetracaine, used for subarachnoid block anesthesia, is an example of this group.
Cocaine, a benzoic acid ester, is another local anesthetic. Used primarily for topical anesthesia of mucous membranes, it is also associated with a high incidence of illegal abuse.


Procaine
Tetracaine
Chloroprocaine

Front 40

What is an amine?

Back 40

May be regarded as derivatives of ammonia (NH3).
***When attached to molecules, they make the molecule more water-soluble.
Many vasopressor drugs used in anesthesia, including phenylephrine, epinephrine, and norepinephrine, have this structure.

Front 41

What is the general formula of an amine?

Back 41

R-NH2

Front 42

***What are some drugs that are amines?

Back 42

phenylephrine, epinephrine, and norepinephrine

Front 43

What is a quaternary base?

Back 43

Quaternary bases are formed from ammonium hydroxide (NH4OH), the hydrogen atoms around the nitrogen being replaced by alkyl radicals.

They have bacteriostatic and germicidal properties. More important to anesthesia, they form an essential part of the structure of muscle relaxants, ganglionic blocking agents, and cholinergic compounds.

Front 44

What is an amide?

Back 44

amides: their hydrogens surrounding the nitrogen atoms are replaced by radicals.

Front 45

How are amides written?

Back 45

Sometimes written as -COHN2. They are related to carboxylic acid.

Front 46

What is the best example of an amide?

Back 46

Lidocaine.

Front 47

What is the best example of the body's end product of protein metabolism?

Back 47

urea

Front 48

How can you distinguish between amides and amines?

Back 48

amines and amides are often confused. Remember, amines retain their hydrogens intact, whereas, in amides, hydrogens attached to the nitrogen are replaced by radicals.

Front 49

Amides constitute what group of local anesthetics?

Back 49

The second main group of local anesthetic compounds.
Lidocaine is the most prominent example

Front 50

What is a representative amino ester local anesthetic?

Back 50

Procaine

Front 51

what is a representative amino amide local anesthetic?

Back 51

Lidocaine

Front 52

What is the general formula for an ether?

Back 52

R-O-R

Front 53

What is an ether?

Back 53

Ethers are organic oxides having the general formula R-0-R.
They consist of two hydrocarbon radicals joined by an atom of oxygen, which is the functional group. Diethyl (C2H5-0-C2H5) and divinyl (C2H3-0-C2H3) ethers have been removed from anesthesia practice because of their volatility and explosiveness.

For years they were anesthetic mainstays, and even today, the public associates the practice of anesthesia with the administration of ether.
The explosive ethers have been replaced by halogenated, non-explosive ones.

Front 54

What will you find in the center of the diethyl ether structure?

Back 54

An oxygen bridge

Front 55

Discuss Methoxyflurane (Penthrane)

Back 55

A pungent, sweet-smelling, potent anesthetic, methoxyflurane
once found wide use in obstetrics
was also later abandoned because of its association with high-output renal failure caused by renal interstitial accumulation of free fluoride atoms. Accumulation of the ions is both time and dose related.

Front 56

Enflurane (Ethrane)

Back 56

Sweet-smelling, nonflammable ether anesthetic.
Not widely used, it is chemically very stable and does not require a preservative (halothane requires a preservative).
Although it too may produce some renal dysfunction by ion accumulation during metabolism, the incidence is significantly less than with methoxyflurane.
Enflurane’s use has fallen in recent years, due to the availability of newer and better agents.

Front 57

Isoflurane (Forane)

Back 57

Its properties are similar to those of enflurane, but induction and recovery periods are slightly shorter.

It's an ethyl-methyl ether

Front 58

How might you distinguish between enthrane and isoflurane?

Back 58

If asked to distinguish these two agents, ethrane and isoflurane, when the structural formulas are given, remember that the F for Forane (the trade name for isoflurane) matches the three fluorines on the end carbon of the larger (ethyl) radical of the structure.

Both enflurane and isoflurane are trifluororoethyl difluoromethyl ethers. The differences between the two drugs are the result of different halogen substitutions at various positions.

Front 59

Desflurane (Suprane)

Back 59

This is the latest halogenated methyl-ethyl ether which differs from isoflurane only by the presence of a fluorine atom instead of chlorine.

Front 60

Desflurane

Back 60

quick acting because it has a low blood gas coefficient

a truly flourinated anesthetic

Only about 0.02% is recoverable in the urine.
The MAC of desflurane decreases with advancing age or administration of other neurologically depressing drugs, such as benzodiazepines and opioids.

Front 61

Sevoflurane (Ultane)

Back 61

Sevoflurane is the most recent available in the US but has been used extensively in Japan and Europe. It is a fluorinated methyl ethyl ether with a pleasant smell and a low blood/gas solubility.

Front 62

What problem are we looking for with Sevo?

Back 62

Toxic Compound A...breakdown in the presence of soda lime

Questions about its safety have arisen with respect to its stability in the presence of soda lime (there may be toxic by-products) and as to the release of fluoride during biotransformation

Front 63

Halothane (Fluothane)

Back 63

Halothane is another halogenated anesthetic compound, but it is not a halogenated ether. Halothane rightfully belongs in the class of halogenated hydrocarbons (a halogenated straight-chain hydrocarbon). It is a saturated compound with a pleasant odor and has been implicated as a possible cause of hepatic damage. It has been largely replaced by sevoflurane.

Front 64

Summary of Halothane

Back 64

Halothane is a halogen-substituted ethane, superior to earlier ethers and alkanes, with or without halogen substitutions. Following its introduction in the 1950's, halothane rapidly replaced other general anesthetic drugs. However, two problems became evident with halothane that led to a systematic search for a superior drug, based on studies of the structure-activity characteristics of anesthetic molecules.

Front 65

Name 1 of 2 problems encountered with Halothane

Back 65

The first problem was an increased incidence of arrhythmias, particularly in the presence of catecholamines. The introduction of the ether link found in enflurane, isoflurane, desflurane, and sevoflurane reduced this tendency markedly.

Front 66

Name the 2nd problem encountered with Halothane

Back 66

The second problem with halothane involved the metabolism or biotransformation of the drug. As much as 20% of the administered dose may be recovered as nonvolatile products in the urine (mainly bromide ions and trifluoroacetic acid). The mixed function oxidases in the endoplasmic reticulum, primarily of the liver, are responsible.

Front 67

More info on Halothane

Back 67

Halothane is also somewhat unstable. Alkaline conditions, such as those that occur in the soda lime of carbon dioxide absorbers, and ultraviolet light, tend to cause breakdown of halothane. Prolonged exposure corrodes metal and degrades some plastic parts of the anesthetic circuit.

Front 68

More info on Halothane

Back 68

The principal factor leading to the decreased use(demise) of halothane has been the rare (<1:10,000) occurrence of hepatitis, generally beginning a few days after halothane anesthesia. The rarity of the phenomenon and the prevalence of hepatic dysfunction and hepatitis in the surgical population at larger have made even the existence of "halothane hepatitis" a subject for debate.

Front 69

More info on Halothane

Back 69

The cause of this syndrome also remains uncertain, but a popular view is that metabolic breakdown products of halothane form hapten-protein conjugates, leading to a fulminant, immunologically mediated hepatic necrosis that may be fatal.
Usually the severe response occurs after halothane has been administered several times to the same patient, and often a retrospective review reveals fever or mild jaundice following a previous exposure to halothane. However, the severity and random occurrence of this complication has hastened the replacement of halothane by other anesthetics, both inhalational and injectable.

The substitution of fluorine for chlorine or bromine in the anesthetic molecule increases stability, while decreasing potency and solubility. In this way, the properties of the newer volatile anesthetics have been improved greatly over those of halothane by the elimination of bromine and the introduction of the ether link.

Front 70

What is the formula for Nitrous Oxide?

Back 70

N2O

Front 71

Is nitrous metabolized by the body. is it harmful?

Back 71

no

Nitrous oxide is a simple linear compound that is stable under the usual physical conditions in which it is used clinically, and is not metabolized in the body. However, nitrous oxide inhibits the enzyme methionine synthetase, and thereby may inhibit DNA synthesis and reduce bone marrow activity.

These sequelae have been observed in humans only with prolonged exposure (several weeks), and such use is contraindicated. There is no evidence that this action of nitrous oxide is harmful when used for surgical anesthesia, where exposure times are measured in hours, not days or weeks.

Interference with vitamin B12 availability by prolonged exposure to N20 may precipitate peripheral nerve dysfunction, which has been reported among dentists chronically exposed to nitrous oxide. These problems do not occur among health care personnel when appropriate scavenging of waste gases is used.