Question

Atracurium is used intravenously as a neuromuscular blocker. 

 The molecule undergoes a chemical degradation at slightly alkaline pH. What is the name of this reaction?

• A. Hofmann rearrangement
• B. Hofmann elimination
• C. Cope rearrangement
• D. McLafferty rearrangement

Answer 1

The Correct Option is B

Step 1: Understanding the Reaction of Atracurium - Atracurium is a neuromuscular blocker that undergoes non-enzymatic degradation at slightly alkaline pH (around 7.4). - The major degradation pathway is Hofmann elimination, which occurs under physiological conditions. - This reaction is temperature- and pH-dependent and does not require hepatic or renal metabolism.


Step 2: Evaluating the Given Options - (A) Hofmann rearrangement: - This reaction involves conversion of amides to amines in the presence of bromine and a strong base, which is not relevant here.
- (B) Hofmann elimination (Correct Answer): - This is a base-catalyzed reaction where quaternary ammonium compounds degrade to produce tertiary amines, alkenes, and alcohols. - This perfectly matches the degradation of Atracurium.
- (C) Cope rearrangement: - A pericyclic reaction involving [3,3] sigmatropic shifts in amines or oximes, unrelated to Atracurium degradation.
- (D) McLafferty rearrangement: - A mass spectrometry fragmentation reaction, not applicable here.


Step 3: Selecting the Correct Answer - Since Atracurium undergoes Hofmann elimination under slightly alkaline conditions, the correct answer is (B) Hofmann elimination.