Recognizing Functional Groups in Drugs and Medications

Summary

This script delves into the world of organic chemistry, focusing on functional groups—the key to understanding molecules' properties and reactivity. It explains how these groups, such as alcohols, ethers, and amines, classify molecules into families and dictate their behavior. The video uses common medications like ibuprofen and morphine to illustrate how specific functional groups contribute to their therapeutic effects, highlighting the profound impact of even minor structural variations on a drug's efficacy and side effects.

Takeaways

• 🧪 Functional groups in organic molecules define their chemical and physical properties, and categorize them into specific families.
• 🔗 Carbon to carbon single bonds are common in hydrocarbons but do not define a molecule's functional group family unless no other functional groups are present.
• 🔑 The presence of a carbon to carbon double bond classifies a molecule as an alkene, while a triple bond places it in the alkyne family.
• 🌐 A six-membered ring with alternating single and double bonds is characteristic of aromatic hydrocarbons, which have distinct properties from alkenes.
• 🍷 Functional groups containing oxygen include alcohols, phenols, ethers, ketones, aldehydes, and carboxylic acids, each with unique properties.
• 🌿 Functional groups with nitrogen include amines and amides, which are essential for various biological activities.
• 💊 Medications like ibuprofen and albuterol have distinct functional groups that contribute to their therapeutic effects and interactions within the body.
• 🔍 Identifying functional groups in drugs involves recognizing heteroatoms and unusual bonding patterns that define their chemical behavior.
• 💡 The structure of a molecule, defined by its functional groups, determines its mechanism of action, as seen in the comparison between aspirin and acetaminophen.
• 🌼 Natural and synthetic molecules can have similar structures but different properties, as demonstrated by the comparison between morphine and codeine.
• 📚 Understanding functional groups is crucial for analyzing the properties and actions of organic compounds, including drugs and medications.

Q & A

What are functional groups in organic chemistry?

Functional groups in organic chemistry are specific atoms or groups of atoms that provide the molecule with specific chemical and physical properties, classify the molecule into a family, and determine the naming of the molecule.

What are the different types of hydrocarbon families mentioned in the script?

The different types of hydrocarbon families mentioned are alkanes (with single bonds only), alkenes (with at least one carbon-carbon double bond), alkynes (with at least one carbon-carbon triple bond), and aromatics (with a six-membered ring and alternating single and double bonds).

How do aromatic hydrocarbons differ from alkenes in terms of properties?

Although aromatic hydrocarbons may appear similar to alkenes in structure, they differ in properties. Aromatic hydrocarbons are more like alkanes in their properties, which is why they are classified into a separate family.

What is the significance of functional groups in the context of medications and drugs?

Functional groups in medications and drugs determine the reactivity, properties, and the way these substances interact with biological receptors, which is crucial for their therapeutic effects.

How does the presence of a carboxilic acid group influence a molecule's properties?

A carboxilic acid group, characterized by a carbon double-bonded to oxygen and with a hydroxyl group (OH) attached to the same carbon, imparts acidic properties to the molecule, allowing it to donate a proton (H+).

What is the difference between an ester and a carboxilic acid?

An ester is a derivative of a carboxilic acid where the hydroxyl group (OH) of the carboxilic acid is replaced by an alkoxy group, while a carboxilic acid has a hydroxyl group attached to the carbon that is also double-bonded to oxygen.

What is the role of the amine functional group in organic molecules?

The amine functional group, which contains nitrogen bonded to carbons or hydrogens, can participate in various chemical reactions and is often involved in the formation of salts, coordination compounds, and can influence the solubility and basicity of the molecule.

How does the presence of an ether functional group affect a molecule?

An ether functional group, which consists of an oxygen atom bonded to two carbon atoms, can affect the molecule's polarity, solubility, and can act as a source of steric hindrance in reactions.

What is the structural difference between aceto salicylic acid (aspirin) and aceto minen (Tylenol)?

Aspirin (aceto salicylic acid) has an ester group and a carboxilic acid group, while Tylenol (aceto minen) has an amide group and lacks the carboxilic acid group, leading to different mechanisms of action and side effects.

How does the structure of procaine relate to that of cocaine?

Procaine is modeled after the structure of cocaine but with modifications to remove groups that contribute to cocaine's addictiveness. Both contain amide and aromatic groups, but procaine is designed to be a safer local anesthetic.

What is the functional group difference between morphine and codeine that leads to their different properties?

Morphine has an alcohol group off the aromatic ring, while codeine has an ether group in that position. This small structural difference results in codeine being less potent as a painkiller but having a lower potential for addiction and better cough-suppressing properties.

Outlines

00:00

🧪 Organic Functional Groups and Medications

This paragraph delves into the significance of organic functional groups in determining the properties and reactivity of molecules. It explains how these groups classify molecules into families like hydrocarbons, alkenes, alkynes, and aromatics, which share similar properties. The paragraph introduces various oxygen-containing functional groups such as alcohols, phenols, ethers, ketones, and carboxilic acids, as well as nitrogen-containing groups like amines and amides. It uses the example of ibuprofen to illustrate how recognizing these groups can help understand a drug's mechanism of action and its classification as an analgesic and fever reducer.

05:03

🌿 Functional Groups in Albuterol and Aspirin

The second paragraph focuses on identifying functional groups in the medications albuterol and aspirin, highlighting their distinct properties and mechanisms despite being analgesics and fever reducers. It emphasizes the importance of heteroatoms and unusual bonds in recognizing functional groups. The summary includes the identification of alcohols, aromatic rings, amines, and the unique classification of phenols as a subclass of alcohols. The paragraph also contrasts the structural differences between aceto salicylic acid (aspirin) and aceto minen (Tylenol), explaining how these differences contribute to their distinct therapeutic effects and side effects.

10:06

💊 Structural Features of Cocaine, Procaine, Morphine, and Codeine

This paragraph explores the structural features and functional groups of cocaine, procaine, morphine, and codeine, highlighting how slight structural variations can lead to significant differences in their effects. It discusses cocaine's addictive properties and how procaine was developed to retain anesthetic qualities without addiction. The paragraph also examines morphine's natural occurrence, its potent painkilling effects, and its side effects, such as reduced respiration. Codeine is compared to morphine, noting the minor structural change that results in different therapeutic effects, with codeine being more effective as a cough suppressant and less addictive.

Keywords

💡Organic Functional Groups

Organic functional groups are specific atoms or arrangements of atoms within organic compounds that are responsible for their characteristic chemical reactions, physical properties, and reactivity. In the video, functional groups are highlighted as the key to understanding the behavior of organic molecules, such as how they interact with other molecules and their role in classifying molecules into families. For example, the presence of a carboxilic acid group (-COOH) in ibuprofen is a key functional group that contributes to its analgesic and anti-inflammatory properties.

💡Hydrocarbons

Hydrocarbons are organic compounds consisting entirely of hydrogen and carbon atoms. The script explains that hydrocarbons can be classified into different families based on the type of carbon-carbon bonds they contain: alkanes (single bonds), alkenes (double bonds), alkynes (triple bonds), and aromatics (a six-membered ring with alternating double bonds). The script uses the example of ibuprofen to illustrate how the presence of an aromatic ring contributes to the molecule's properties.

💡Aromaticity

Aromaticity refers to a special type of chemical bonding found in certain organic compounds, characterized by a ring of atoms with delocalized electrons. These compounds, such as benzene, have unique stability and reactivity. In the script, aromatic rings are mentioned as a type of hydrocarbon family that, despite appearing similar to alkenes, have properties more akin to alkanes and are crucial in the structure of drugs like ibuprofen.

💡Alcohols

Alcohols are a class of organic compounds where a hydroxyl group (-OH) is attached to a carbon atom. The script distinguishes between general alcohols and phenols, a subclass of alcohols where the hydroxyl group is directly bonded to an aromatic ring. Phenols are highlighted as having unique properties and are found in drugs like albuterol.

💡Ethers

Ethers are organic compounds characterized by an oxygen atom connected to two carbon atoms (R-O-R'), forming a C-O-C bond. In the script, ethers are mentioned as part of the functional groups present in morphine, where they contribute to the molecule's overall structure and properties.

💡Ketones

Ketones are organic compounds containing a carbonyl group (C=O) bonded to two carbon atoms. The script explains that ketones are part of the functional groups that give molecules specific properties and are found in various organic molecules, including some medications.

💡Carboxilic Acids

Carboxilic acids are organic compounds with a carboxyl group (-COOH), which contains a carbonyl group and a hydroxyl group. The script uses the example of ibuprofen to show how the carboxilic acid group is a key part of the molecule's structure, contributing to its reactivity and function as an analgesic.

💡Esters

Esters are organic compounds derived from carboxilic acids where the hydroxyl group is replaced by an alkoxy group. The script points out that esters are present in some organic molecules and drugs, such as aspirin, where they contribute to the molecule's overall reactivity and properties.

💡Amines

Amines are organic compounds that contain nitrogen with three bonds to carbon atoms or, in some cases, two bonds to carbons and one to hydrogen. The script discusses amines as functional groups that play a role in the structure and properties of various drugs, including albuterol and cocaine.

💡Amides

Amides are a functional group with a carbonyl group (C=O) bonded to a nitrogen atom, which is also bonded to a carbon atom. The script explains amides as part of the functional groups that contribute to the properties of organic molecules, such as in the structure of Tylenol.

💡Pharmacophore

The pharmacophore is the ensemble of structural features responsible for the biological activity of a molecule. In the script, the term is used to describe the common structural features of procaine and cocaine that allow procaine to act as a local anesthetic, modeled after the structure of cocaine but without the addictive properties.

Highlights

Functional groups are key to understanding the properties and reactivity of organic molecules.

Functional groups provide specific chemical and physical properties to molecules and classify them into families.

Members of the same organic family exhibit similar physical properties and reactions.

Hydrocarbons are classified into alkanes, alkenes, alkynes, and aromatics based on carbon-carbon bonding.

Aromatic hydrocarbons resemble alkenes in structure but have properties more akin to alkanes.

Functional groups containing oxygen include alcohols, phenols, ethers, aldehydes, ketones, and carboxylic acids.

Nitrogen-containing functional groups are amines and amides, which are crucial in organic chemistry.

Ibuprofen's functional groups, including a carboxilic acid and an aromatic ring, contribute to its analgesic properties.

Albuterol's functional groups, such as alcohols and an aromatic ring, are responsible for its bronchodilator effects.

Aspirin and acetaminophen, despite being analgesics, have different functional groups and mechanisms of action.

Cocaine and procaine share structural similarities, with procaine being a modified version for reduced addictiveness.

Morphine's functional groups, including alcohols, an ether, an amine, and an alkene, contribute to its potent painkilling properties.

Codeine differs from morphine by a single functional group change, resulting in different therapeutic effects and reduced addictiveness.

The presence of heteroatoms and unusual bonds is a key indicator for identifying functional groups in organic molecules.

Phenols, a subclass of alcohols, exhibit unique properties due to their direct bonding to an aromatic ring.

Esters and carboxylic acids are differentiated by the presence of hydrogen in the latter, affecting their reactivity and properties.

Transcripts

so let's talk about organic functional

groups they're where the action is in

organic

molecules remember functional groups

provide the properties for the molecule

they give the molecule specific chemical

and physical properties they classify

the molecule into one or more families

they provide naming portions especially

the ending of the name and the key

feature is that members of the same

organic family have similar physical

properties and often very similar

reactions you have a chart of functional

groups first let's take a really quick

look at the functional groups for carbon

to carbon bonds the carbon to carbon

bonds are single bonds and there are no

other important groupings then the

molecule belongs to the hydrocarbon

family alkan if anywhere in the molecule

there's a carbon to carbon double bond

then that compound belongs to the

hydrocarbon family

alken if anywhere in the molecule

there's a carbon to carbon triple bond

then that molecule belongs to the

hydrocarbon family alkine

if the molecule contains this unusual

grouping which is a six-membered ring

with alternating single and double bonds

all the way around the ring this

particular structural feature places the

molecule in a different hydrocarbon

family the hydrocarbon family

aromatic aromatics have some

similarities to alkenes in terms of what

they look like they seem to have carbon

to carbon double bonds but in terms of

their properties they're actually much

more like alkanes they needed to be put

in a different family because in spite

of the appearance in this picture they

are not alkenes they are their own

family there are a large number of

functional groups which contain oxygen

alcohol C single Bond o single Bond

H phols which are a special case of

alcohol with an O bonded directly to one

of the carbons of an aromatic ring these

are sometimes called aromatic alcohol

usually called

phols alahh C double bond o and one side

of the C has to have an H Ketone C

double bond o and on both sides of that

carbonal carbon are other

carbons ethers C single Bond o single

Bond c carboxilic acid C double bond o

that same C has an o h single bonded to

it that whole CL cluster is a carboxilic

acid it's not two groups put together

it's one group see double bond o single

Bond o single Bond H Esther which is

considered a derivative of the

carboxilic acid where we have the same

grouping except where there's an H in a

carboxylic acid there are additional

carbons in an

Esther there are two functional groups

containing nitrogen that are part of

this course amans where this looks very

complicated but all it's really trying

to say is that there's a nice nitrogen

with three bonds to it and at least one

of the bonds has to be to a carbon it

can be all three bonds to carbons two

bonds to carbons or just one bond to

carbon but to be an organic compound at

least one of these bonds has to be to

carbon and then there is an amide which

is a functional group containing both

oxygen and nitrogen it has C double bond

o and that same carbon is single bonded

to a nitrogen that area makes this an

amide

so let's go looking for organic

functional groups in some medications

and drugs the goal here is to learn to

recognize the cluster that makes that

area of the molecule belong to a certain

functional group family so here's the

drug ibuprofen an over-the-counter

endset analgesic fever reducer let's

look for functional groups in it when

you're looking for functional groups

remember to look for hetero atoms things

other than carbon and also unusual bonds

so here's an area that might be

interesting and here's an area that

might be inter interesting otherwise we

just seem to have a lot of carbon to

carbon single Bond every organic

compound is going to have some carbon to

carbon single Bonds in it so we never

use the family alkan unless there's

nothing else going on in the molecule so

in spite of all these carbon to carbon

single bonds this molecule will not be

placed in

alkanes this area will create some

functional group behavior and this area

will see if you can figure out what

those groups are by referring to a

functional group chart eventually you

need to be able to recogn recognize the

functional groups without reference to a

chart so there's one cluster cbond o o

Ah that's a carboxilic acid here's the

other interesting area a six-membered

ring with alternating single and double

bonds aha if I look that up that's one

of the hydrocarbon functional groups

that's an aromatic those two groups will

give this molecule its reactivity its

properties and actually are a big part

of why it acts as an analgesic

there's another medication albuterol

I've already highlighted one of the

functional groups C single Bond O8 can

you find any other areas of Interest

there's actually quite a few in this

there's something going on here here

here and here so let's try identifying

some of these refer to your functional

group

chart there's some more alcohols alcohol

alcohol alcohol

then what's this this is that

hydrocarbon group alternating single and

double bonds all the way around to Six

membered Ring that's an aromatic so

what's going on over

here that is a nitrogen bonded to a

carbon bonded to a hydrogen and bonded

to another carbon so that's a nitrogen

with three single bonds to it that's an

amine so this molecule has all of those

functional groups and its character its

performance its ability to do what it

does which is be a Bronco dilator comes

from those different groupings and how

those groupings allow it to interact

with various receptors in the body one

of the alcohols in this molecule should

actually be classified slightly

differently it's an alcohol group an O

connected directly to a carbon of an

aromatic ring that makes it a phenol a

subclass of alcohols with their own

unique properties can you find the

phenol

here's two molecules that are sometimes

considered very similar but in fact if

you look at their structures they're

quite different the one on the left

aceto salicylic acid is aspirin and the

one on the right aceto minen is Tylenol

they actually are both analgesics and

fever reducers but they do not act on

the same system in the body aspirin can

handle certain kinds of pain prostag

gland and induced pain that

acetominophen simply cannot touch

acetominophen can cause liver toxicity

aspirin can cause blood clotting issues

so they have very different groups and

it's the very different groups that make

their mechanism of action different but

for now let's just look for the groups

so remember focus on hetero atom and

unusual bonding and let's see what we

can

find there we go C C double bond o some

carbons over here and then what's on the

other side oh an oxygen okay c bond o o

so does it have an h no so it's not a

carboxilic acid it has more carbons

couble Bond o o c that makes that an

Esther and then what else do we have

well we've got another one of those

aromatic rings and what else do we have

ah here's our carboxilic acid see double

bond o single Bond o h look at the

difference between an Esther and a

carboxilic acid see double bond o o and

carbons see double bond o o and an

H so we have an Esther an aromatic and a

carboxilic acid and it turns out that

all three of those regions are very

important in getting this molecule to

interact with the enzyme it essentially

shuts down the production of the

prostaglandins that cause inflammatory

pain

so how about a CED minin here we have a

group C double bond o single Bond n oh

well that's see double bond o single

Bond n that's an

amide and then we have another one of

those

aromatics and then we have an alcohol

hanging off over here so we have amide

aromatic alcohol and again there's an

alcohol in Tylenol that would be better

classed as a phenol quite different than

Esther aromat IC carboxilic acid very

different structures very different

mechanisms of action so let's compare

cocaine and procaine novocaine they're

actually more related to each other than

you might think cocaine has an

amine it has two Esters C double bond o

single Bond o carbons C double bond o

single Bond o carbons

Esters and it has an

aromatic this area right here is called

called a bicyclic ring it's two rings

that are only partially connected to

each other that's a very important

structural feature in cocaine but it

isn't any kind of specific functional

group so here's procane we still have an

amine we have an Esther see double Bondo

single Bond o and carbons we have an

aromatic and we have another amine way

out over here so this molecule actually

has a lot of the functional group

features and if you kind of count it

carefully if we start here at this amine

which has carbons on all three places

this amine has carbons on all three

places and we have just one

two three carbons till we get to an

Esther or one two three carbons till we

get to an Esther so here from this

nitrogen we have one two carbons till we

get to an Esther a little bit shorter

then we have the Esther and there's an

Esther on an aromatic ring just like

down here and so actually this structure

right here is very much like Watch Me

Trace

that part of cocaine and in fact those

common structural features are part of

what let procaine be used as local or

topical anesthetic a local anesthetic

cocaine would also be a great local

anesthetic except it's so addictive that

you don't use it that way but procaine

is actually built off of the structure

of cocaine modeled after cocaine with

the removal of the groups that seem to

cause the addictive nature for example

this particular is a really bad actor in

this structure it keeps what it needs to

be able to be an anesthetic and got rid

of what was there in cocaine that caused

the addictiveness of the molecule and

its name actually speaks to its

parentage procaine came from cocaine not

naturally but made in the laboratory to

model this particular grouping of

cocaine which is called its

pharmacophore so how about more morphine

and Codine we have a similar kind of

thing going on here except that nature

did this so here we have two alcohol

groups what else do we have in the

structure of morphine well there's

another one of those aromatics and then

we have oh an N with carbons to three

single bonds that's an amine and what's

this over here C single Bond o single

Bond C it also closes a ring but that's

an ether then we've got one more

functional group in morphine can you

find

it see this different bond that makes an

alken so morphine has two alcohols one

on an aromatic ring it has an ether in a

cyclic system it has an amine this is

actually called a tertiary amine because

all three groups are carbon and it has

an

alken opium poppies make this compound

naturally this compound is a fantastic

painkiller unfortunately it's addictive

it's also got anti-tussive behavior in

other words it can reduce cough it

reduces respiration too which is a

negative thing about it so what about

Codine opium poppies also make Codine

let's compare its functional groups to

Morphine it's got an

alcohol it's got that same

alken it's got that same tertiary amine

boy they're looking awfully

similar got an

aromatic oh here's a difference this has

an alcohol off the aromatic ring and

this has C single Bond o c and ether off

the aromatic R and then we have one more

functional group right here an ether

COC so they have essentially identical

structures with this one difference an

alcohol off the aromatic ring and

morphine and an ether off the aromatic

ring encoding that doesn't seem like a

very huge difference instead of an H we

have a ch3 but that actually makes their

behavior very very different Codine

isn't a particularly good painkiller

having that group allows more to go

places and do things that this grouping

does not Codine is pretty good at

reducing cough and Codine has less

addictive nature than morphine does that

one tiny change appears to be tiny

change o to

O3 creates the very large difference in

their property all of this that stays

the same is why they can act similarly