116103-17-4

Upstream product

• 624-83-9 methyl isocyanate 
• 116103-16-3 (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol 
• 107485-89-2 (3aS,8aS)-5-Methoxy-3a,8-dimethyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid ((S)-1-phenyl-ethyl)-amide 
• 104069-11-6 (3aS,8aR)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 116103-15-2 (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole 
• 100-39-0 benzyl bromide 

Downstream Products

• 6091-57-2 (-)-eseramine 

Relevant academic research and scientific papers

Synthesis and Anticholinesterase Activity of (-)-N1-Norphysostigmine, (-)-Eseramine, and Other N(1)-Substituted Analogues of (-)-Physostigmine

(-)-N1-Benzylnorphysostigmine (4), prepared from synthetic (-)-O-methyl-N1-noreseroline (1) by N-benzylation, ether cleavage, and reaction of (-)-N1-benzylnoreseroline (3) with methyl isocyanate, was the intermediate used to prepare the title compounds.Catalytic debenzylation of (4) afforded (-)-N1-norphysostigmine (5), and (-)-eseramine (6) was obtained by reaction of 5 with methyl isocyanate.Reductive N-methylation of 5 gave (-)-physostigmine (9) while reaction of 5 with allyl bromide and phenethyl bromide afforded carbamates 7 and 8, respectively.Data on the in vitro potencies (IC50) and activities of certain of these compounds (4-8) as inhibitors of electric eel acetyl cholinesterase are reported. (-)-N1-Norphysostigmine (5) was found to be similarly potent against AChE as (-)-physostigmine (9).