Functional Groups

Naming Amide

"amide"

Isopropyl group is attached at the center atom- more common in medical literature- give an example

2-[4-isobutylphenyl] prpanoic acid is- ibuprofen

Why do we care about drugs metabolized by p450 Enzymes?

A young robust patient that is large and occassionally drinks will need more of the drugs that we administer, then an elderly person that never drinks. - Genetic Variability People can be enzyme inhibited or enzyme induced based on genetics, or drinking, or medications taken. People that drink alcohol is enzyme induced

Famous Phenols

Adrenaline (water soluble), Propofol (lipid soluble- WORKS FAST- single OH in center does not make it soluble), Morphine (2 hydroxol groups attached)

Amino-Amide

Amides used more often then Amin-Esters. Amino Amides consist of lidocaine, ropivacaine, bupivacaine Amides are not as fast as wearing off as Amino Esters - Ropivacaine, Bupivacaine used in pain pumps for LONG acting pain relief •Amides are very stable, more so than the esters •Amide hydrolysis is slower than ester hydrolysis •"differing durations of action of these drugs lies in the difference in their molecular structure and resonance stability"

Procaine

Amino ester local anesthetic

Lidocaine

Amino-amide

secondary alcohol

An alcohol in which the hydroxyl (-OH) group is attached a carbon that is attached to two other carbons. •- the carbon atom carrying the -OH group is attached to two other carbon atoms

Carbonyl

C=O

Ibprofen is a

Carboxylic Acid

Naproxen is a

Carboxylic Acid

Aspirin is a

Carboxylic Acid- know which is the acid

Acetylcholine has

Ester Linkage

Aromatic Amines

aniline

Tertiary Amines can

cross the blood brain barrier

The polarity of the carbonyl group and its ability to form hydrogen bonds with water molecules allows small aldehydes and ketones to be

highly water soluble ("like dissolves like").

diethyl ether

most famous "ether" early anesthesthetic

Acetophenone

simplest aromatic ketone

The polar covalent C-O and O-H bonds and the ability to form hydrogen bonds give phenols

with low molecular weight a high degree of water solubility.

Importance of Amides

•Peptide bond - amide bonds hold proteins together •lactams - cyclic amide (B-lactam) •Amide local anesthetics - lidocaine, ropivacaine, bupivacaine

Phase 1 reactions (most drugs metabolized in the liver)

***Oxidation**, reduction, hydrolysis

Phase 2 reactions

***glucuronidation*** •sulfation •acetylation glutathione

Properties of ethers

1. Are insoluble in water. 2. They are used as solvents for organic compounds 3. Are extremely flammable. •Low water solubility—WHY? •Unfluorinated ethers are combustible •Diethyl ether = explosive •Addition of halogens •Rather unreactive

Amines are classified based on the number of carbon atoms directly attached to the nitrogen atom.

1.primary (1°) - only one carbon atom attached to the amine nitrogen atom 2.secondary (2°) - two attached carbon atoms 3.tertiary (3°) - three attached carbon atoms 4.quaternary (4°) ammonium ions - four carbon atoms are directly attached to the nitrogen atom and the nitrogen carries a +1 charge.

Naming Ethanol

2 Carbon with alchol attached- add "anol"

Carbonyl Group

A Carbonyl group is a carbon doubly bonded to oxygen. The bonding arrangement is VERY STRONG and occurs frequently in the chemical world. Carbonyl Functional Groups is derived by supplying various hydrogen, carbon, oxygen, and nitrogen-based substituents to the carbonyl carbon. ❍The carbonyl functional groups include Aldehydes Ketones Carboxylic Acids Esters Amides

ester group

A chemical group consisting of a carbon double bonded to oxygen and single bonded to another oxygen (must be in middler of chain)

racemic mixture

A mixture that contains equal amounts of the (+) and (-) enantiomers. Racemic mixtures are not optically active. Can not be superimposed on itself. They're different

Alcohol Group

Alcohols have a hydrogen atom directly bonded to an oxygen atom, therefore alcohols can form hydrogen bonds. If the R Group contains three or fewer carbon atoms, the alcohol is perfectly soluble in water. If the R group becomes larger, the solubility in water decreases. The functional group of an alcohol is the Hydroxyl Group, OH- since the hydroxyl group is covalently bonded to the carbon chain, alcohols do not contain a hyroxide ion, there alcohols are not strong bases. 2 Functional Groups, Alcohols and Ethers are both derivatives of water. Is we replace on Hydrogen on the water molecule with an alkyl group then we have an alcohol. If we replace BOTH Hydrogen with alkyl groups, we have an ETHER. To name alcohols - add the suffix "ol" to the name of the parent and indicate the position on the hydroxyl group with a locant number

Anti-buse drug

Aldehyde - the body has trouble getting rid of Aldehydes- so when a person takes Anti-buse and drinks- it creates a lot of aldehydes and makes the person sick- making drinking less attractive.

Aldehyde

Aldehydes have an alkyl group and a hydrogen atom bonded to a carbonyl group. Aldehydes are easily oxidized to carboxylic acids, even by the oxygen in the air- making them rare to find. Aldehydes in medicine are Carbohydrates.

Haloalkane

Alkane with halogen substituents- the halogens are named as halo groups= fluoro, bromo, chloro, and iodo Name the alkyl halide by naming the alkyl group and then the halide- Alkyl halides If the parent compound is a benzene, then the halogenated derivatives are called aryl halides R= the generic alkyl group (ie. methyl or ethyl) and X- a generic halide Haloalkanes + Ether = Common anesthetic agents Examples include- Propyl Chloride, Choloroform (old anesthetic- no longer used because of toxicity), Halothane, and Isopopyl Bromide Not dissoluble in water

Symbol R (hydrocarbon) - (OH) = hydroxyl group

Alkene + OH= R-OH

Geraniol

Alkene - Alcohol

Tertiary alcohol

An alcohol in which the hydroxyl (-OH) group is attached to a carbon that is in turn attached to three other carbons. the carbon atom carrying the -OH group is attached to three other carbon atoms

Alkyl Halide

An alkane in which one of the hydrogens has been replaced by a halogen.

Formation of Amides

Carboxylic Acids react with amines to form amides. The hydrolysis of amides requires harsher reaction conditions than the hydrolysis of esters, and this is good. Esters in triglycerides bind fatty acids to glycerin- triglyceride. We need to tear the tyiglycerides back apart to access chemical energy stored in fatty acids. Proteins on the other hand are polymers held together by amide bonds. We need our structural proteins to be VERY DURABLE to withstand all the water in our bodies. Our stomachs are the harshest chemical conditions in our bodies.

Formation of an ester

Carboxylic acids react with alcohols to form esters.

Quaternary Amine

Charged - Always Ionized= Polar Molecule thus it's HYDROPHOBIC No electrons that can accept a hydrogen- therefore it doesn't have acid base properties

Ketones (Diabetes)

Decreased Insulin

Succinylcholine is a

Ester The only Depolarizing NM Blocker we have - quickly dissolved into alcohol and acid

Pro-Drugs are

Ester and Amides Esters- Rapid Break Down and they go away quickly

Mivacuronium

Ester drug Trade Name: Mivacron Duration: 15-20 min Mechanism: Non-depolarizing blockade of muscle nicotinic receptors Elimination: plasma cholinesterase Rx: Intubation or muscle relaxant during surgery or ventilation

Local Anesthetics exist in two classes

Esters and Amides Ester anesthetic- benzocaine, procaine, and tetracaine Amide Anesthetics- bupivacaine, etidocaine, lidocaine, mepivacaine, ropivacaine, prilocaine

Ester

Esters are condensation products between acids and alcohols. Carbonyl with an R on one side= carboxylic acid and an O-R on the other= derived from alcohol Most esters have a pleasant fruity odor. Fragrance and flavor industry. Ester functional group binds three fatty acid molecules to a glycerin backbone, forming a triglyceride.

Ether

Ether is an oxygen bridge between two alkyl groups. Ether's are our ANESTHETIC REAGENTS! R-O-R Ethers are nonreactive in organic chemistry, so they are often used as solvents and protecting groups that hide the much more reactive hydroxyl group of alcohols. Diethyl ether, also known as ethyl ether or simply ether, is one of the most common solvents in organic chemistry. Diethyl ether is extremely flammable and is rarely used today. Ethers are Alkoxy Alkanes. The larger R Group is named as the alkane, and the smaller R group along with the oxygen atom is named as an alkoxy substituent. The most common anesthetic gases are halogenated ethers. Notice the "theme-and-variation" relationship between these compounds. Researchers moved and exchanged halogen atoms around on the same basic skeleton in a systematic attempt to fine-tune the physiological properties of the substance.

Naming Ethers

Ethers are Alkoxy Alkanes. The larger R Group is named as the alkane, and the smaller R group along with the oxygen atom is named as an alkoxy substituent.

Oxidation-reaction (redox)

Every electron that is lost by one atom through oxidation is gained by another atom through reduction •increased number of oxygen bonds •Catalyzed by the P450 cytochrome system •

Amines

Functional group derived from AMMONIA (NH3). So, amines are nitrogen analogs of alchols, and the chemistry of the two functional groups are similar. The generic formula of an amine is R3N, where R can either be alkyl groups or hydrogen atoms, in any combination. So, R3N, R2NH, or RNH2 are all generic formulas of amines. Like alcohols, amines can form hydrogen bonds and tend to be more soluble in water then any other functional classes. Amines are Basic. Most amines have a noticeable base strength and will accept a proton from a strong acid to form its conjugate acide. The conjugate acid of an amine is called an ammonium salt. The ionic salt is much more soluble in water then the electrically neutral free-base form. So, by controlling the pH of the medium, you can control the solubility of many medications. Because amines are weak bases, naturally occurring amines are called alkaloids. The alkaloid dissolves in water, the solution becomes very slightly alkaline. A large number of medications are amines. Mechlorethamine one of the first anticancer, chemotherapy drugs

Halothane

General anesthetic prototype: inhaled halogenated hydrocarbon. Causes cardiovascular and respiratory depression and relaxes skeletal and smooth muscle. Use has decreased due to sensitization of heart to catecholamines, and occurrence (rare) of hepatitis and malignant hyperthermia

The most common Anesthetic Gases are

Halogenated Ethers The most common anesthetic gases are halogenated ethers. Notice the "theme-and-variation" relationship between these compounds. Researchers moved and exchanged halogen atoms around on the same basic skeleton in a systematic attempt to fine-tune the physiological properties of the substance. Shubert, David, PhD; Leyba, John, PhD; Niemann, Sharon, DNAP, CRNA. Chemistry and Physics for Nurse Anesthesia, Third Edition (p. 333). Springer Publishing Company. Kindle Edition.

heteroaromatic compounds

Hetero means other. So heteroaromatic compounds have one or more atoms other than carbon in the ring. Nitrogenous means that the other atom is a nitrogen atom. As you can probably guess from Figure 11.30, there is a staggering variety of heteroaromatic compounds. Pyridine is the most common heteroaromatic compound, but purine and pyrimidine are the templates upon which the genetic bases are built. Pyrrole and imidazole are both based on a five-membered ring and occur frequently in many biologically important molecules.

Amino- Ester

Hydrolysis metabolism - much shorter half life

Metabolism of Amides

Hydrolysis- Amide + water >>> Carboxylic acid + amine Oxidation

Phenol Group

Hydroxy Group bonded to a benzene ring.

Fatty acid - Carboxylic Acids

Identify these molecules and the functional group on them.

Phenol Group

In the simplest phenol, named phenol, the -OH group is the only group attached to a benzene ring.When substituents are added to this molecule, the carbon atom carrying the -OH is designated as carbon 1.-Weak acid-easily conjugated

Sevoflurane

Inhalation anesthetic

Medically Important Ketones

Ketamine, Oxycodone, Methadone, Progesterone two alkyl groups bonded to a carbonyl group.

Medically Important Amines

Ketamine, Quinine, Mechlorethamine, Dopamine, Epinepherine, Serotonin

Oxycodone

Ketone Group- two alkyl groups bonded to a carbonyl group.

Ketamine

Ketone group- two alkyl groups bonded to a carbonyl group.

Ketone

Ketones have two alkyl groups bonded to a carbonyl group. Ketones are very common in nature, and form a variety of natural compounds and medicines.

Esters physical properties

Less polar than R-OH & R-COOH •Loss of hydroxyl group limits solubility •Hydrogen bonding?? •Slightly soluble in water •BP is < R-OH or R-COOH •Odor and taste Naming add -ate

amino-amide local anesthetics 1. derivative 2. list common examples

Lidocaine, Ropivicaine, Bupivacaine benzene ring at one end- with amide at the other

Amino Acids

Made of Amines and Acids

Bupivacaine

Marcaine

If something is charged will it cross the blood brain barrier?

No- being charged makes it polar- (is this hydrophilic or hydrophobic) Lipophilic Non Polar Non Charged and CAN CROSS a membrane

Propofol is a

Phenol- aromatic alcohol- Propofol- Not soluble in water because it has 12 carbon atoms, and is much more soluble in hydrophobic solvents. Propofol suspended in soybean oil and water- An egg based phospholipid (Lecithin) is added to stabilize that emulsion. Flavored water-soybean oil-lecithin mixture= MAYONNAISE.

Aromatic alcohols are called

Phenols Phenol itself, formerly known as carbolic acid, finds application as a preservative Propofol- Not soluble in water because it has 12 carbon atoms, and is much more soluble in hydrophobic solvents. Propofol suspended in soybean oil and water- An egg based phospholipid (Lecithin) is added to stabilize that emulsion. Flavored water-soybean oil-lecithin mixture= MAYONNAISE.

When a benzene ring is a stick-on group it is called a

Phenyl Group

Hydroxy Group adds

Polarity •Water solubility increases with # of -OH's •Polarity (electronegativity) •Hydrogen bonding •Water solubility decreases with more carbons •"Weak acid"

Aldehydes and Ketones

Prefer Nucleophilic ADDITION (vs carboxylic acids -> Nucleophilic Substitution). Know: Aldehyde (RCOH), formaldehyde/methanal (HCOH), ketone (RCOR), acetone/2-propanone (CH3COCH3). More polar and have higher BP than alkanes and alkenes of similar MW, but cannot H bond with each other so lower BP than corresponding alcohols. Aldehydes and ketones with up to 4 Cs are soluble in water (and readily form hydrate). Aldehydes are slightly more acidic than ketones (alkyl groups are EDG). --> Accept H bonds - makes H2O, etc excellent solvents for these substances. Mostly act as the substrate in Nucleophilic Addition or as a Brownsted-Lowry acid by donating an α-H (corresponding ion is the enolate with negative charge). Adding an alcohol (ROH) to an aldehyde (R'COH) or ketone (R"COR"') forms the hemiacetal R'HC(OH)OR and hemiketal R"R"'C(OH)OR respectively. --> Aldehydes can be oxidized to carboxylic acids while ketones cannot.

Amino Esters

Procaine, Novacaine, Coccaine, tetracaine

Desflurane

Pungent inhaled anesthetic which leads to high incidence of coughing and vasospasm

Acetylcholine

Quaternary Amine

Ethers

R-O-R Alcohols and Ethers are both derivatives of water. If we replace one hydrogen on the water molecule with an alkylg group, we have an alcohol. If we replace BOTH HYDROGENS with alkyl groups we have an ETHER.

Alcohol

R-OH

Sulfide

R-S-R

L-bupivacaine

Racemic version of Bupivacaine- Levo-Bupivacaine is safer because it's not cardio toxic. Then why don't we use it all the time? It's too expensive. Bupivacaine alone is cheap.

Reduction

Reduction is the gain of electrons- opposite of oxidation. So, when the number of bonds to oxygen decreases or the number of bonds to hydrogen increases, the species has undergone reduction.

Carbonic Acid VS Alcohol

See how far away the OH is

Aromatics

Sometimes called arenes, have a functional group called a benzene ring. Very common in nature because they are ESPECIALLY STABLE and are frequently found in medications

thiol

Sulfur in the center instead of an oxygen Ethanethiol

Esters used for

Taste and smell

carboxylic acid

The functional group of a carboxylic acid, is the carboxyl group, which is a carbonyl group with a hydroxyl group bonded to the carbonyl carbon. Carboxylic acids are important intermediates in metabolism, and fatty acids are long-chained carboxylic acids that we use as our principal long-term energy storage molecules. One application of carboxylate anions is to serve as biologically inert anions for positively charged medications. For example, the citrate ion is commonly used as a counterion for positively charged medications, for example, sildenafil citrate (Viagra).

ESTERIFICATION

The reaction of an alcohol with a carboxylic acid to produce an ester and water. (ESTER SYNTHESIS)

Aspirin

There is a ring= Arene an OH bound to a Carbonyl= Carboxylic Acid Toward the middle- Oxygen bound to a carbonyl, bound to an Arene - with an ester on the other side

Thiobarbiturates

Thiamylal Secobarbital Sulfur containing is more ?combustible?

Mercaptan is another name for

Thiols

Phase 1 metabolism

Uses enzymes (oxidases) to unmask or introduce polar groups (ex. -OHs, -O's) on the drug Phase 1 mainly uses: CYTOCHROME P450 which are Heme-containing enzymes. Start with a drug and make it more water soluble- Drug + o2 > one O ends up binding to the new drug, and the other binds to an H2O molecule. Where do the hydrogens come from? They come from NADPH-(part of Pentose Phosphate Shunt) NADPH acts as a reducing agent- which means it can reduce other molecules- Reduction, Oxidation, hydrolysis. Usually yields slightly polar, water-soluble metabolites (often still active). Geriatric Patients lose this first.

Phase 2 metabolism

Uses enzymes (transferases) to attach small endogenous POLAR MOLECULES to a drug. Glucuronate, sulfate, acetate = Conjugation reactions in which a polar molecule is linked to a suitable functional group on a drug or one of its Phase 1 metabolites •Conjugation of the drug or the product of phase 1 metabolism •Glucuronic acid, sulfuric acid or acetic acid • •Leads to a more polar compound (more ionized) • •Body synthesizes a new compound

Most famous Carboxylic Acid

Vinegar= acetic acid

Aldehydes and Ketones

___ and ___ are more polar and have higher boiling points than alkanes of similar weight. They cannot hydrogen bond with one another, so they have lower boiling points than corresponding alcohols.

Hyperresponders

_____________ may demonstrate clinical signs and symptoms of local anesthetic overdose at blood levels that are considerably lower than those normally necessary to produce such reactions.

Hyporesponders

______________ may not experience any adverse reaction until local anesthetic blood level is considerably above "normal" overdose threshold.

ADME process (we're interested in what? because-)

absorption, distribution, metabolism, excretion - For us- we're interested in Metabolism because that is the breakdown of functional groups

Naming Amines

adding "amine"

Naming Esters

aklyl alkanoates- the portion of the ester derived from the alcohol is named as an alkyl group. The portion of the ester derived from carboxylic acid is named as the conjugate base of that acid. The half derived from the carboxylic acid has the carbonyl group.

primary alcohol

an alcohol in which the hydroxyl (-OH) group is attached to a carbon that is attached to no more than one other carbon. - the carbon atom carrying the -OH group is attached to one other carbon atom

Carboxyl Acid

an organic compound containing a carboxyl group

Amide

are condensation products between carboxylic acids and amines. The Amine is the R-N-R in blue, while the grey double bound Carbon Oxygen= the carboxylic acid. The R groups on the nitrogen can either by alkyl groups or hydrogens. PROTEINS are the most biologically important examples of amides.

Hydrocarbons

contain only hydrogen and carbon- Hydrocarbon functional groups = Alkanes, Alkenes, Alkynes, and Arenes (aromatic compounds)- little medical applications because they're FLAMMABLE and are typically- gas

Amine

diethylamine Morphine, Nicotine, Caffeine

Naming Ketones

drop "e" add "one" the simplest ketone is Propanone= acetone Acetone is an excellent solvent for most organic compounds and is the main ingredient in fingernail polish remover. Acetone is one of the ketone bodies that build up in the bloodstream from excessive metabolism of fats. = Ketosis or "acetone breath"

to name aldehydes

drop "e" from the end of the alkane name and replace it with "al" The simplest aldehyde is Methanal= commonly called formaldehyde- is a highly toxic gas used to preserve biological specimens. Ethanal is the next aldehyde

Inflorine

inhaled anesthetic

Oxidation

loss of electrons- Oxidation may be manifest by an increase in ionic charge (Fe2+ > Fe3+) In organic chemistry we find it easier to recognize oxidation as increasing the number of bonds to oxygen or decreases the number of bonds to hydrogen- oxidation has occurred. Oxidation represents the chemical pathway to extract the chemical potential energy stored in the carbon-hydrogen and carbon-carbon bonds in an organic molecule. Carbohydrates are already partially oxidized. Fats have a much higher carbon to oxygen ratio, this is why carboydrates contain fewer calories per gram than fats. Alcohols are oxidized to give ketones or aldehydes, depending on the substitution pattern on the alcohol. Aledhydes and ketones are reduced to alcohols. Notice that when going from an alcohol to an aldehyde or ketone, two hydrogent atoms are rmoved, while at the same time, the carbon oxygen bond order increases from a single bond to a double bond. In reduction the reverse is true.

Glycerin is

nontoxic, and serves as the backbone that holds fatty acids into triglycerides- if you add Nitric or Sulfuric acids introduces 3 nitro groups (-NO2) into hydroxyl groups and affords NITROGLYGERIN. It is used in explosives or to treat angina.

Famous Thiols

pentothal (was the drug of choice before Propofol)

All drugs are

poisons

Reduction Reactions

reactions in which a molecule acquires electrons and gains energy. •decreased number of oxygen bonds and increase the number of hydrogen bonds •Catalyzed by the P450 cytochrome system

Compared to hydrocarbons with a similar molecular weight, alcohols have

relatively high boiling points

2 propanol, isopropanol, and isopropyl alcohol all =

rubbing alchol

Hydrolosis

the chemical breakdown of a compound due to reaction with water. •catalyzed by esterases

Functional Groups

the components of organic molecules that are most commonly involved in chemical reactions •A functional group is an atom, groups of atoms, or bond that gives a molecule a particular set of chemical properties, function and activity. •Each family of organic compounds is defined by the functional group that its members contain. 2 Functional Groups, Alcohols and Ethers are both derivatives of water. Is we replace on Hydrogen on the water molecule with an alkyl group then we have an alcohol. If we replace BOTH Hydrogen with alkyl groups, we have an ETHER.

saturated compounds contain...

the maximum number of hydrogen atoms for a given number of carbon atoms. Alkenes and cycloalkanes have FEWER Hydrogen atoms per carbon atom than alkANES, therefore, compounds that contain double bonds or rings are called UNSATURATED.

If the compound has more than one hydroxyl group you need to include

the prefix multiplier

BIOTRANSFORMATION

the process in which enzymes convert a drug into a metabolite that is itself active, possibly in ways that are substantially different from the actions of the original substance •"if we knew quantitatively all of the factors affecting the distribution, elimination, and sensitivity to a drug in an individual patient, we could predict the time course of drug effects exactly. • However, we only know a minority of the factors...understanding of one important factor generally does not explain the bigger picture

The -OH group of phenols allows these molecules

to form hydrogen bonds with one another and, as a result, phenols tend to have relatively high boiling points and many are liquids at room temperature

The simplest alcohol =

wood alcohol= Methanol Methanol itself is low toxicity, however when oxidized by the liver (metabolized) it forms fomaldehyde, and then formic acid= both of which are toxic

Pharmacologic esters

•Amino-ester local anesthetics -Cocaine, Chloroprocaine, Procaine, Tetracaine • •Succinylcholine • •Mivacuronium

Physical properties of Carboxylic Acids

•Carboxyl group is polar •Form hydrogen bonds •High boiling point -BP of R-COOH is > R-OH •LMW (< 5 C) compounds are water soluble •4-20 C compounds called 'fatty acids'

carboxyclic acid

•Compared to other organic compounds with a similar molecular weight, carboxylic acids have relatively high boiling points due to their ability to form hydrogen bonds with one another. • • •The ability to form hydrogen bonds, in addition to the presence of polar C=O, C-O, and O-H bonds, gives small carboxylic acids a significant water solubility. -As we have seen before, an increasing number of carbon atoms leads to a reduction in water solubility. Runs the Krebs cycle

Importance of esters

•Drugs prepared as esters convert to acids & alcohols in vivo •Would this property be beneficial? Drugs can be administered and rapidly broken down into an alcohol and an acid- (RBC esterase) and work at its site of action

Metabolism of esters

•Ester hydrolysis •React with water -Ester carboxylic acid + alcohol • •Carboxylic acid drugs are hydrophilic. Make a drug into a ester and it can then reach it site of action. Then it can be hydrolyzed into the active carboxylic acid. IF A DRUG IS METABOLIZED QUICKLY IT IS BECAUSE OF ESTER HYDROLOSIS Succinylcholine- undergoes ester hydrolosis -

Naming Ethers

•Only the most simple ethers have an ether name •Diethyl ether •Ethers are alk"OXY" alkanes •1,1,1,3,3,3-hexafluoro-2-(fluoromethoxy)propane (sevo) •Larger R group named as an alkane •The smaller R group is an alkoxy substituent

Metabolism of Amines

•Oxidation •Deamination •removal of an amino group from a molecule •MAO (Mono Amine Oxidase) can catalyze these reactions Anti Anxiety medications MAOI's MAO INHIBITOR- Mono Amine Oxidase- breaks up epinepherne, ephedrine, norepinepherine

Physical properties of Amines

•Polar compounds (N) •N less electronegative than O •Amines water solubility < alcohols but > alkanes •Ability to hydrogen bond depends on N substitutents- •Primary & tertiary amines form weak hydrogen bonds NITROGEN act as weak Base drugs - Why do amines function as a base?- Acids have a H+ to give up, Bases have the ability to accept those Hydrogen's

Thiols Group

•Similar physical properties to ethers •Foul-smelling compounds (sulfur containing component) •Skunk spray •Flatulence •Garlic •Sewage •Rotten eggs •Added to Natural gas (to allow it to be detected)

Naming Amines (From Class)

•To name a 1°, 2°, or 3° amine using IUPAC rules, the parent, the longest chain of carbon atoms attached to the amine nitrogen atom, is numbered from the end nearer the point of attachment of the nitrogen. •The parent chains of amines are named by dropping "e" from the name of the corresponding hydrocarbon and adding "amine." •If an amine is 2° or 3°, the carbon-containing groups attached to the nitrogen atom that are not part of the parent chain are substituents and N is used to indicate their location (N-methyl, N,N-diethyl, etc.). •Simple amines, those with a relatively few number of carbon atoms, are often identified by common names by placing "amine" after the names of the groups attached to the nitrogen. methylamine = CH3NH2

Reactions of ethers

•Undergo substitution (e.g., halogenation) •decreases flammability •increases stability •decreases potency • •Relatively non-reactive (why is this important?) • •Other metabolism hydroxylation

PROPERTIES OF AMIDES (PRO-DRUG)

•Weak bases- like amines- because Nitrogen group can accept hydrogen bonds- making them weak bases. •Hydrogen bonding- yes does work •High boiling points •Why?- because it's stable •Water soluble this is the HIGHEST Water Soluble Functional Group More than the carboxylic acids and alcohols Amide quickly broken down to carboxylic acid and Amine

Naming Carboxylic Acids

•When naming a carboxylic acid according to the IUPAC rules, the parent is the longest continuous carbon chain that includes the carboxyl group. •Numbering begins at the carboxyl carbon, and alkyl groups are identified by name, position, and number of appearances. •IUPAC names for carboxylic acid parent chains are formed by dropping the final "e" on the name of the corresponding hydrocarbon and adding "oic acid".

Naming Aldehydes and Ketones

•When naming aldehydes and ketones according to the IUPAC rules, the carbonyl (C=O) must be part of the parent chain, which is numbered from the end nearer this group. •Since the carbonyl carbon atom of an aldehyde is always in position number 1, its position is not specified in the name. •For ketones, however, the position of the carbonyl carbon is given, unless the molecule is small enough that there is no question as to carbonyl placement. •Parent chains are named by dropping the final "e" from the name of the corresponding hydrocarbon and adding "al" for aldehydes or "one" for ketones.

Naming Alcohols

•When the IUPAC rules are used to name an alcohol, the parent (the longest continuous carbon chain carrying the -OH group) is numbered from the end nearer the -OH and named by dropping the "e" ending on the name of the corresponding hydrocarbon by adding "ol." •When a parent chain contains more than two carbon atoms, the position of the -OH group must be specified with a number. •Any alkyl groups attached to the parent chain are identified by name, position, and number of appearances.

Properties of Thiols

•electronegativity of sulfur? •similar to Carbon- not a lot of electronegativity difference- (.4)- no polarity •Polar or nonpolar? •Non Polar •Boiling points? •Low Boiling points because it lacks hydrogen bonding hydrogen bonding?> No