Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from ecgonine or cocaine.

[4] The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

[13][14] Thus, reaction of methyldiazobutenoate (2) with 5 equiv of N-((2-(TMS)ethoxy)carbonyl)pyrrole (1) in the presence of rhodium(II) hexanoate/hexane gave the [3.2.1]-azabicyclic system (R/S)-8 in 62% yield.

The unsubstituted double bond was selectively reduced using Wilkinson catalyst to provide N-protected anhydroecgonine methyl ester ((R/S)-4).

Following deprotection of N8 nitrogen with TBAF and reductive methylation with formaldehyde and sodium cyanoborohydride, (R/S)-5 was obtained in overall good yield.