Eseroline

Base Information

• Chemical Name: Eseroline
• CAS No.: 469-22-7
• Molecular Formula: C13H18 N2 O
• Molecular Weight: 218.299
• UNII: Q22H41O18D
• DSSTox Substance ID: DTXSID30891448
• Nikkaji Number: J1.556.718J
• Wikipedia: Eseroline
• Wikidata: Q5397651
• Metabolomics Workbench ID: 57117
• ChEMBL ID: CHEMBL310934
• Mol file: 469-22-7.mol

Synonyms:eseroline;eseroline monohydrochloride, (3aS-cis)-isomer;eseroline, (+)-;eseroline, (3aR-cis)-isomer

Chemical Property of Eseroline

Chemical Property:

• Vapor Pressure: 6.99E-06mmHg at 25°C
• Boiling Point: 366.3°Cat760mmHg
• Flash Point: 189.6°C
• PSA: 26.71000
• Density: 1.16g/cm³
• LogP: 1.76420
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 218.141913202
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

98% ^*data from raw suppliers

ESEROLINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)O)C)C
• Isomeric SMILES: C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)O)C)C
• Description: Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated through the μ-opioid receptor.
• Uses: (-)-Eseroline is a metabolite of physostigmine, displaying both anti-acetylcholinesterase and opiate agonist activities.

Technology Process of Eseroline

There total 53 articles about Eseroline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

Physostigmin (57-47-6) → eseroline (469-22-7)

Guidance literature:

With sodium; In butan-1-ol; at 20 ℃;

DOI:10.1016/j.bmcl.2010.01.097

Reference yield: 76.0%

(-)-esermethole (65166-97-4) → eseroline (469-22-7)

Guidance literature:

With boron tribromide; In dichloromethane; 1.) -78 deg C; 2.) 10 deg C;

DOI:10.1248/cpb.30.2641

Reference yield: 71.3%

glacial HOAc + m-chlorophenyl isocyanate (2909-38-8) + Physostigmin (57-47-6) → eseroline (469-22-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran;

upstream raw materials:

(3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole

physostigmine

2-iodo-4-methoxy-N-methylaniline

(Z)-2-Methyl-4-triisopropylsilanyloxy-but-2-enoic acid

Downstream raw materials:

physostigmine

(-)-(3aS)-1-benzyl-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydro-5-methoxypyrrolo[2,3-b]indole

(-)-cymserine

1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl 2,6-diisopropylphenylcarbamate

Refernces

• 1、 Schammel, Alex W.,Chiou, Grace,Garg, Neil K.. "Synthesis of (+)-phenserine using an interrupted Fischer indolization reaction". . p. 725 - 728. Retrieved 2012/03/26.
• 2、 Huang, Audris,Kodanko, Jeremy J.,Overman, Larry E.. "Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine". . p. 14043 - 14053. Retrieved 2007/10/03.