Podcast
Questions and Answers
Which type of amines are susceptible to oxidative N-dealkylation, oxidative deamination, and N-oxidation reactions?
Which type of amines are susceptible to oxidative N-dealkylation, oxidative deamination, and N-oxidation reactions?
What type of reaction leads to the formation of lactam metabolites in alicyclic tertiary amines?
What type of reaction leads to the formation of lactam metabolites in alicyclic tertiary amines?
In the metabolism of which drug does bisdealkylation of the tertiary aliphatic amine occur very slowly?
In the metabolism of which drug does bisdealkylation of the tertiary aliphatic amine occur very slowly?
Which group remains intact and does not undergo significant metabolism in many β-adrenergic antagonists?
Which group remains intact and does not undergo significant metabolism in many β-adrenergic antagonists?
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Which type of amines proceed with N-dealkylation through the carbinolamine pathway?
Which type of amines proceed with N-dealkylation through the carbinolamine pathway?
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Which type of amine drugs are susceptible to oxidative N-dealkylation reactions?
Which type of amine drugs are susceptible to oxidative N-dealkylation reactions?
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What is the primary amine metabolite formed from oxidative dealkylation of secondary amines susceptible to?
What is the primary amine metabolite formed from oxidative dealkylation of secondary amines susceptible to?
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Which process involves an initial α-carbon hydroxylation reaction to form a carbinolamine intermediate?
Which process involves an initial α-carbon hydroxylation reaction to form a carbinolamine intermediate?
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What can direct oxidative deamination of secondary amines produce?
What can direct oxidative deamination of secondary amines produce?
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Which type of amines can be metabolized to their corresponding lactam derivatives?
Which type of amines can be metabolized to their corresponding lactam derivatives?
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What do N-hydroxylamine metabolites generated from secondary aliphatic and alicyclic amines undergo?
What do N-hydroxylamine metabolites generated from secondary aliphatic and alicyclic amines undergo?
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In the metabolism of propranolol, what reaction leads to the formation of the carbinolamine intermediate?
In the metabolism of propranolol, what reaction leads to the formation of the carbinolamine intermediate?
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What is the key role of metabolism of nitrogen functionalities like amines and amides?
What is the key role of metabolism of nitrogen functionalities like amines and amides?
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Which enzyme is primarily responsible for oxidative N-dealkylation of tertiary aliphatic and alicyclic amines?
Which enzyme is primarily responsible for oxidative N-dealkylation of tertiary aliphatic and alicyclic amines?
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What is the initial step in the oxidative N-dealkylation process of tertiary aliphatic and alicyclic amines?
What is the initial step in the oxidative N-dealkylation process of tertiary aliphatic and alicyclic amines?
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Why is N-dealkylation of the t-butyl group not possible by the carbinolamine pathway?
Why is N-dealkylation of the t-butyl group not possible by the carbinolamine pathway?
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Which type of functional groups are commonly found in natural products like morphine, cocaine, and nicotine?
Which type of functional groups are commonly found in natural products like morphine, cocaine, and nicotine?
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What is the main outcome of the spontaneous heterolytic cleavage of the C–N bond during oxidative N-dealkylation?
What is the main outcome of the spontaneous heterolytic cleavage of the C–N bond during oxidative N-dealkylation?
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Study Notes
Types of Amines and Reactions
- Tertiary amines are susceptible to oxidative N-dealkylation, oxidative deamination, and N-oxidation reactions.
- Secondary amines can be metabolized to lactam derivatives.
Lactam Formation
- Lactam metabolites in alicyclic tertiary amines arise from a specific reaction type.
Drug Metabolism
- Propranolol demonstrates slow bisdealkylation involving tertiary aliphatic amines.
- Some β-adrenergic antagonists maintain intact aromatic hydroxyl groups, reducing significant metabolism.
Carbinolamine Pathway
- Secondary amines proceed with N-dealkylation through the carbinolamine pathway.
- The oxidative N-dealkylation of tertiary aliphatic and alicyclic amines involves an initial α-carbon hydroxylation to create a carbinolamine intermediate.
Metabolite Formation
- The primary amine metabolite from oxidative dealkylation of secondary amines is susceptible to further reactions.
- Direct oxidative deamination of secondary amines can yield aldehydes or ketones.
N-Hydroxylamine Metabolites
- N-hydroxylamine metabolites derived from secondary aliphatic and alicyclic amines generally undergo further reactions.
Enzyme Involvement
- Cytochrome P450 enzymes are primarily responsible for oxidative N-dealkylation of tertiary aliphatic and alicyclic amines.
Mechanisms and Cleavage
- The initial step in the oxidative N-dealkylation process involves a hydroxylation reaction.
- N-dealkylation of t-butyl groups does not occur via the carbinolamine pathway due to steric hindrance.
Functional Groups in Natural Products
- Common functional groups found in natural products, such as morphine, cocaine, and nicotine, include amines and amides.
Cleavage Outcomes
- Spontaneous heterolytic cleavage of the C–N bond during oxidative N-dealkylation typically results in the formation of a carbonyl compound and an amine.
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Description
Learn about the process of oxidative dealkylation leading to primary amine metabolites, which are susceptible to oxidative deamination. The pathway involves initial α-carbon hydroxylation, formation of carbinolamine intermediate, and subsequent carbon–nitrogen cleavage.
