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Chapter # 18

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AminesOrganic compounds containing nitrogen

N 5 valence e-s :. 3 bonds(octet)

Primary, secondary, and tertiary amines

N with 4 bonds = ammonium ion

H I

CH3 – N+ – H I HMethyl ammonium ion

H I

CH3 – N+ – H Cl-

I HMethyl ammonium chloride

H I

H – N+ – H I HAmmonium ion

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Ending N

Middle N

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COMMON Naming simple amines

Diamines

Aromatic amines use the name aniline

List the names of the alkyl groups bonded to the N atom in alphabetical order + suffix -amine.

Amines are associated with unpleasant smells ranging from fishy to plain rotten. Diamines are even worse.

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Like water and alcohols, amines are Brønsted bases (proton acceptors):

Amines react with acids to produce ammonium salts

Properties of amines

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Quaternary (4˚) amines = ammonium salts

Ammonium salts are ionic and therefore:solids at room TodorlessSoluble in water and body fluids

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When the ammonium salt reacts with a strong base amine (also called the free amine or free base)

Cocaine Is sold illegally as an amine salt.Is reacted with NaOH to produce the free amine form known as “crack”.

It becomes less polar and therefore more soluble in fat cells in the body. As a result it is more potent.

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Novocain, a local anesthetic, is the trade name for the amine salt of procaine.

Procaine is a local anesthetic drug of the amino ester group. Procaine was first synthesized in 1905 and is the oldest man-made local anesthetic still in clinical use.

Procaine is used less frequently today since more effective (and hypoallergenic) alternatives such as lidocaine (Xylocaine) exist. Prior to the discovery of procaine, cocaine was the most commonly used local anesthetic.

Heterocyclic Amines and Alkaloids

A heterocyclic amine

• Is a cyclic organic compound.

• Has a five- or six-atom ring.

• Contains one or more nitrogen atoms.

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• Alkaloids

• Physiologically active nitrogen-containing compounds.

• Generally produced by plants but some are of non-plant origin.

• Used as stimulants, anesthetics, and antidepressants.

• Often habit forming.

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Caffeine• Is a stimulant of the central nervous system. • Is found in coffee beans, tea, chocolate, and soft

drinks.• Contains an imidazole ring.

Nicotine• Increases the adrenaline level in the blood.• Causes addiction to tobacco.• Contains a pyrrolidine ring.

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MorphineAlkaloids such as morphine and codeine are produced by the opium poppy (Papaver somniferum).• Have been used for centuries as painkillers.• heroin and codeine are modifications of morphine.

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Vicodin

Vicodin is a combination of hydrocodone and acetaminophen (Tylenol). Hydrocodone is a synthetic opiate, meaning its chemical structure is based on the chemical structure of opium. Other such drugs include oxycodone, dilaudid, fentanyl and morphine.

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This Is Life With Lisa Ling | Season 1, Episode 2 - 'Unholy Addiction'

hydrocodone

acetaminophen

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Amides

In amides, an amino group(–NH2) replaces the –OH group of carboxylic acids.

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Preparation

Amidation = reaction of a carboxylic acid with ammonia or a 1˚ or 2˚ amine to produce an amide.

Carboxylic acid + amines or ammonia amides

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Amides in Health and Medicine

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Hydrolysis of Amides

acid hydrolysis

base hydrolysis

carboxylic acid + ammonium salt

salt of carboxylic acid + an amine or ammonia

Treatment of an amide (RCONHR') with water in the presence of an acid catalyst (HCl) forms a carboxylic acid (RCOOH) and an amine salt (R'NH3+ Cl−).

Amides are also hydrolyzed in aqueous base to form carboxylate anions and a molecule of ammonia (NH3) or amine.