Aromatic Amine

Definition

A primary aromatic amine is a homocyclic (strictly carbon-based) or heterocyclic (usually both carbon and nitrogen-based) conjugated ring structure that contains a primary amine (-NH₂) substituent directly attached to the ring. As many as 12 % of all of the substances listed by the U.S. National Toxicology Program as being a known or probable human carcinogen is a primary aromatic amine or a compound that can be converted into one. The simplest aromatic amine is aniline. N-acetylation of primary aromatic amines by arylamine N-acetyltransferase (NAT) enzymes is considered to be detoxifying since the product of the reaction is chemically stable. On the other hand, aromatic amines can be bioactivated to DNA-damaging electrophiles by a metabolic sequence of N-oxidation of the primary amino group by cytochrome P450 enzymes followed by O-acetylation either by NAT or by other O-conjugating enzymes such as sulfotransferases and UDP-glucuronosyltransferases. Examples of aromatic...