Nicotine undergoes phase I metabolism by a reaction with CyP450 that gives a compound A. In the presence of water, compound A is converted spontaneously into compound B, with which it is in equilibrium. (See Fig. P17.52)

(a) Use what you know about the reactions of CyP450 to suggest a structure for compound B.

(b) Assuming the presence of H₃O⁺ and H₂O, provide a curved-arrow mechanism for the conversion of A into B.

Transcribed Image Text:

H CH3 nicotine (form present at pH 7) Figure P17.52 CyP450 A H₂O+ H₂O B H H CH3