Oxidative Dealkylation and Oxidative Deamination in Drug Metabolism

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Which type of amines are susceptible to oxidative N-dealkylation, oxidative deamination, and N-oxidation reactions?

Secondary amines

What type of reaction leads to the formation of lactam metabolites in alicyclic tertiary amines?

Oxidation reaction

In the metabolism of which drug does bisdealkylation of the tertiary aliphatic amine occur very slowly?

Lidocaine

Which group remains intact and does not undergo significant metabolism in many β-adrenergic antagonists?

<p>N-t-butyl group</p> Signup and view all the answers

Which type of amines proceed with N-dealkylation through the carbinolamine pathway?

<p>Primary amines</p> Signup and view all the answers

Which type of amine drugs are susceptible to oxidative N-dealkylation reactions?

<p>Aliphatic tertiary amines</p> Signup and view all the answers

What is the primary amine metabolite formed from oxidative dealkylation of secondary amines susceptible to?

<p>Oxidative deamination</p> Signup and view all the answers

Which process involves an initial α-carbon hydroxylation reaction to form a carbinolamine intermediate?

<p>Oxidative dealkylation</p> Signup and view all the answers

What can direct oxidative deamination of secondary amines produce?

<p>Aldehyde metabolite and alkylamine</p> Signup and view all the answers

Which type of amines can be metabolized to their corresponding lactam derivatives?

<p>Secondary alicyclic amines</p> Signup and view all the answers

What do N-hydroxylamine metabolites generated from secondary aliphatic and alicyclic amines undergo?

<p>Further oxidation to nitrone derivatives</p> Signup and view all the answers

In the metabolism of propranolol, what reaction leads to the formation of the carbinolamine intermediate?

<p>$\alpha$-carbon hydroxylation reaction</p> Signup and view all the answers

What is the key role of metabolism of nitrogen functionalities like amines and amides?

<p>Synthesis of natural products and important drugs</p> Signup and view all the answers

Which enzyme is primarily responsible for oxidative N-dealkylation of tertiary aliphatic and alicyclic amines?

<p>Cytochrome P450 (CYP) mixed-function oxidase enzymes</p> Signup and view all the answers

What is the initial step in the oxidative N-dealkylation process of tertiary aliphatic and alicyclic amines?

<p>Alpha-carbon hydroxylation</p> Signup and view all the answers

Why is N-dealkylation of the t-butyl group not possible by the carbinolamine pathway?

<p>Absence of alpha-carbon hydroxylation</p> Signup and view all the answers

Which type of functional groups are commonly found in natural products like morphine, cocaine, and nicotine?

<p>Aromatic and heterocyclic nitrogen compounds</p> Signup and view all the answers

What is the main outcome of the spontaneous heterolytic cleavage of the C–N bond during oxidative N-dealkylation?

<p>Release of a secondary amine and a carbonyl moiety</p> Signup and view all the answers

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