University of California, San Diego

• CHEM 140C

• Introduction • Organic derivatives of ammonia. • Many are biologically active. => 21-2 Biological Activity • Neurotransmitters: dopamine • Bioregulators: epinephrine • Vitamins: niacin, B 6 • Alkaloids: nicotine, morphine, cocaine • Amino acids Chapter 21: Amines 21-3 Classification of Amines and Nomenclature Amines are related to ammonia in the same sense that ethers and alcohols are related to water. In the amines, the number of alkyl or aryl groups on the nitrogen atom defines the designation of primary, secondary, tertiary and quaternary: • Primary (1 ): one C-N bond, 2 N-H bonds. • Secondary (2 ): two C-N bonds, 1 N-H bond. • Tertiary (3 ): three C-N bonds, no N-H bond. • Quaternary (4 ): four C-N bonds, nitrogen has a + formal charge. Aliphatic amines are named as alkanamines; the name of the alkane stem is modified by replacing the ending – e with –amine. Similar to alcohol nomenclature, except now more than one alkyl group can be present on the nitrogen. Chapter 21: Amines 21-4 Nomenclature (cont’d) Aromatic amines (or anilines) are called benzenamines. Heterocylic amines have a variety of unique names (Chapter 25). For secondary and tertiary amines, the largest alkyl substituent on nitrogen is chosen as the alkanamine stem. Other groups are named using N-, followed by the name of the additional