Organic Chemistry,7th Edition L.G.Wade,Jr. H CH2CH3 Chapter 19 Amines Copyright 2010 Pearson Education,Inc
Chapter 19 Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7th Edition L. G. Wade, Jr. Amines
Biologically Active Amines CH3 O CH-CH2NH2 CH3 -OCH3 O-C-Ph CH3O OCH3 CH OCH3 OH OH H cocaine nicotine mescaline morphine in coca leaves in tobacco in peyote cactus in opium poppies Copyright2010 Pearson Prentice Hall,Inc. The alkaloids are an important group of biologically active amines,mostly synthesized by plants to protect them from being eaten by insects and other animals. Many drugs of addiction are classified as alkaloids. Chapter 19 2
Chapter 19 2 Biologically Active Amines ▪ The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals. ▪ Many drugs of addiction are classified as alkaloids
Biological Activity of Amines Dopamine is a neurotransmitter. -Epinephrine is a bioregulator. -Niacin,Vitamin B6,is an amine. -Alkaloids:nicotine,morphine,cocaine Amino acids Chapter 19 3
Chapter 19 3 Biological Activity of Amines ▪ Dopamine is a neurotransmitter. ▪ Epinephrine is a bioregulator. ▪ Niacin, Vitamin B6 , is an amine. ▪ Alkaloids: nicotine, morphine, cocaine ▪ Amino acids
Classes of Amines Primary (19:Has one alkyl group bonded to the nitrogen(RNH2) -Secondary (2:Has two alkyl groups bonded to the nitrogen(R2NH). Tertiary (39:Has three alkyl groups bonded to the nitrogen (R3N). -Quaternary (49:Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(RN). Chapter 19
Chapter 19 4 Classes of Amines ▪ Primary (1): Has one alkyl group bonded to the nitrogen (RNH2 ). ▪ Secondary (2): Has two alkyl groups bonded to the nitrogen (R2NH). ▪ Tertiary (3): Has three alkyl groups bonded to the nitrogen (R3N). ▪ Quaternary (4): Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(R4N + )
Examples of Amines -NH2 N CH3 Primary Secondary Tertiary (1) (2) (3) Chapter 19 5
Chapter 19 5 Examples of Amines NH2 N H N CH3 Primary (1º) Secondary (2º) Tertiary (3º)