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Introduction to Nomenclature and Structure of Amines

In the IUPAC system of nomenclature, functional groups are usually entitled in one of two ways. The existence of the function may be indicated by a feature suffix and a location number. This is general for the carbon-carbon double and triple bonds that have the respective suffixes ene and yne. Alternatively, Halogens do not have a suffix and are named as substituents, for an instance: (CH3)2C=CHCHClCH3 is 4-chloro-2-methyl-2-pentene. If you are unsure about the IUPAC rules for nomenclature you should reconsider them now.

Amines are derivatives of ammonia where one or more of the hydrogens has been changed by an alkyl or aryl group. The nomenclature of amines is complex by the fact that various distinct nomenclature systems present, and there is no clear preference for one over the others. Additionally, the terms primary (1º), secondary (2º) & tertiary (3º) are employed to classify amines in a entirely different way than they were employed for alcohols or alkyl halides. When applied to amines these terms consider to the number of alkyl (or aryl) substituents bonded to the nitrogen atom, where in other examples they consider to the nature of an alkyl group. The four compounds displayed in the top row of the following picture are all C4H11N isomers. The first two are categorized as 1º-amines, because only a single alkyl group is bonded to the nitrogen; though, the alkyl group is primary in the first instance and tertiary in the second instance. The third and fourth compounds in the row are 2º and 3º-amines correspondingly. Nitrogen bonded to four alkyl groups will essentially be positively charged and is called a 4º-ammonium cation. For an instance, (CH3)4N(+) Br(-) is tetramethylammonium bromide.

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The IUPAC names are listed first and colored blue in the diagram. This system names amine functions as substituents on the largest alkyl group. An amino group is the simple -NH2 substituent found in 1º-amines. For 2º and 3º-amines a compound prefix (example dimethylamino in the fourth instance) includes the names of all but the root alkyl group.
The Chemical Abstract Service has adopted a nomenclature system wherein the suffix -amine is attached to the root alkyl name. For 1º-amines like butanamine (first instance) this is analogous to IUPAC alcohol nomenclature (-ol suffix). Additional nitrogen substituents in 2º and 3º-amines are selected by the prefix N- before the group name. Those CA names are colored magenta in the diagram.
At last, a common system for simple amines names each alkyl substituent on nitrogen in alphabetical order, followed through the suffix -amine. These are the names specified in the last row (colored black in the diagram).
Several heterocyclic and aromatic amines are known by distinctive common names, the origins of which are frequently not known to the chemists that use them often. Because these names are not based on a rational system, it is essential to memorize them.

Natural Nitrogen Compounds

Nature abounds with nitrogen compounds, several of which take place in plants and are considered as alkaloids. Structural formulas for a number of representative alkaloids and other nitrogen consisting of natural products are shown below, and we can identify many of the basic structural features listed above in their formulas. So, Serotonin and Thiamine are the 1º-amines, Coniine is a 2º-amine, Morphine and Quinine are 3º-amines, Atropine, and Muscarine is a 4º-ammonium salt.

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