1. Chapter # 18 1

2. 2 Amines Organic compounds containing nitrogen N 5 valence e-s :. 3 bonds(octet) Primary, secondary, and tertiary amines N with 4 bonds = ammonium ion H I CH 3 – N + – H I H Methyl ammonium ion H I CH 3 – N + – H Cl - I H Methyl ammonium chloride H I H – N + – H I H Ammonium ion

3. 3 Ending N Middle N

4. 4 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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6. 6 Like water and alcohols, amines are Brønsted bases (proton acceptors): ammonium salts Amines react with acids to produce ammonium salts Properties of amines

7. Quaternary (4˚) amines = ammonium salts Ammonium salts are ionic and therefore: solids at room T odorless Soluble in water and body fluids 7

8. 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. 8

9. 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. 9 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.

10. 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. 10 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. \ˈpyu̇r-ˌēn\\pī-ˈri-mə-ˌdēn\ \ˈpir-ˌōl\ \ˌi-mə-ˈda-ˌzōl\ \ˈpir-ə-ˌdēn\ \pə-ˈräl-ə-ˌdēn\ \pī-ˈper-ə-ˌdēn\

11. 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. 11 Morphine Alkaloids 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.

12. 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. http://www.youtube.com/watch?v=gMGWrpN728A&feature=related 12 This Is Life With Lisa Ling | Season 1, Episode 2 - 'Unholy Addiction' hydrocodone acetaminophen

13. Amides 13 In amides, an amino group(–NH 2 ) replaces the –OH group of carboxylic acids.

14. Preparation Amidation = reaction of a carboxylic acid with ammonia or a 1˚ or 2˚ amine to produce an amide. 14 Carboxylic acid + amines or ammonia  amides

15. Amides in Health and Medicine 15

16. 16 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 (NH 3 ) or amine.