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Groups Containing One Nitrogen Atom

Amines Rule C-811 General

811.1 - Bases in which nitrogen forms part of a ring are named as heterocyclic compounds in accordance with Section B of these Rules. The termination "-ine", "-ole", or "-ete" of such names is not considered to be a suffix in the sense of Rule C-10.3, and so may be followed by endings to denote a substituent of the heterocycle, as, for example, in 2-quinolinol (I) or 4-thiazolecarboxylic acid (II). However, the endings denoting quaternary atoms (see Rule C-816) are considered as suffixes, and substituents must then be named by prefixes, as, for example, in 2-carboxypyridinium chloride (III). In the same way as "-ium" the ending "-amine" (see below) is considered as a suffix.

811.2 - The generic name "amine'' is applied to compounds NH2R, , and , which are called primary, secondary, and tertiary amines, respectively. In a wider sense, compounds containing nitrogen in a ring and owing their basicity to this atom may also be referred to as "amines".

811.3 - An -NH2 group, when not the principal group, is named by the prefix "amino-".

Examples to Rule C-811.3

Note: In Beilstein's Handbuch der organischen Chemie use of the prefix "amino-" is permitted as an alternative, when -NH2 is the principal group, but this method is not recommended here; it leads to names such as 1-aminobutane, 2-aminopentane, and 1-aminoanthracene.

811.4 - Radicals RNH-, R2N-, and are named as substituted amino groups by changing "ine'' of the amine to "ino".

Examples to Rule C-811.4

The following are examples of trivial names which are retained:

See Recommendations'93 R-5.4

Amines C-812, C-813, C-814, C-815, C-816
Amides and Imides C-821, C-822, C-823, C-824, C-825, C-826, C-827
Nitriles, Isocyanides, and Their Derivatives C-831, C-832, C-833, C-834
Hydroxylamines and Related Compounds C-841, C-842, C-843
Nitroso and Nitro Compounds C-851, C-852
Amine Radical Ions C-861

This HTML reproduction of Sections A, B and C of IUPAC "Blue Book" is as close as possible to the published version [see Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. Copyright 1979 IUPAC.] If you need to cite these rules please quote this reference as their source.

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