6091-57-2

Basic information

• Product Name: Eseramine
• Synonyms: Eseramine;(3aS,8aS)-3,3a,8,8a-Tetrahydro-N,3a,8-trimethyl-5-[(methylcarbamoyl)oxy]pyrrolo[2,3-b]indole-1(2H)-carboxamide
• CAS NO: 6091-57-2
• Molecular Formula: C16H22N4O3
• Molecular Weight: 318.37
• Mol File: 6091-57-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 527.3°C at 760 mmHg
• Flash Point: 272.7°C
• Appearance: /
• Density: 1.242g/cm³
• Vapor Pressure: 3.29E-11mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: Eseramine(CAS DataBase Reference)
• NIST Chemistry Reference: Eseramine(6091-57-2)
• EPA Substance Registry System: Eseramine(6091-57-2)

Safety Data

• Hazardous Substances Data: 6091-57-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H22N4O3/c1-16-7-8-20(14(21)17-2)13(16)19(4)12-6-5-10(9-11(12)16)23-15(22)18-3/h5-6,9,13H,7-8H2,1-4H3,(H,17,21)(H,18,22)/t13-,16-/m0/s1

Upstream product

• 624-83-9 methyl isocyanate 
• 116103-18-5 (-)-N¹-norphysostigmine 
• 116103-15-2 (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole 
• 104069-11-6 (3aS,8aR)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 116103-16-3 (-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol 
• 116103-17-4 N¹-benzylnorphysostigmine 
• 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 

Relevant articles and documents

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).