microsomal cytochrome P450, to form 19 (Scheme 3).49 Isolated 19 contained a furano-trideuteromethyl group, indicating that a labile intermediate must have been formed during the course of the reaction to allow interchange of the positions of the two allylic methyl groups prior to hydroxylation, ring closure, and aromatization.
5.05.2.1.2.4 Carbon atoms a to a heteroatom (N, O, S, and X)
N-Dealkylation is a frequently encountered metabolic reaction. It is often responsible for the production of the major metabolite obtained from an N-alkyl containing drug. Its prominence does not simply derive from the commonality of an alkyl-substituted amino group as an important part of the structural motif of many drugs. It arises primarily as a consequence of N-dealkylation being energetically favored.10 Typical examples include the N-demethylation of methamphetamine (20)50 (eqn ), the N-deethylation of lidocaine (22)51 (eqn ), and the N-deisopropylation of propranolol (24)52 (eqn ), to form the secondary amines 21, 23, and 25, respectively.
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