Mesembrine

Base Information

• Chemical Name: Mesembrine
• CAS No.: 468-53-1
• Molecular Formula: C17H23NO3
• Molecular Weight: 289.375
• Mol file: 468-53-1.mol

Synonyms:3a-(3,4-Dimethoxyphenyl)octahydro-1-methyl-6H-indol-6-one;(3aR,7aR)-3a-(3,4-Dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one;

Chemical Property of Mesembrine

Chemical Property:

• Vapor Pressure: 3.09E-07mmHg at 25°C
• Refractive Index: 1.548
• Boiling Point: 419.2 °C at 760 mmHg
• PKA: 8.78±0.40(Predicted)
• Flash Point: 207.3 °C
• PSA: 38.77000
• Density: 1.133 g/cm³
• LogP: 2.33660
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

(3AR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methylhexahydro-1H-indol-6(2H)-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An alkaloid used in preparing Channa, a drug of Southwest Africa. A serotonin-uptake inhibitor; occurs naturally as the (-)-form.

Technology Process of Mesembrine

There total 202 articles about Mesembrine 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: 82.0%

(-)-Mesembranol (23544-42-5) → (-)-mesembrine (468-53-1,6023-73-0,21104-37-0,24880-43-1,28639-24-9,35056-46-3,35056-47-4)

Guidance literature:

With dmap; [2,2]bipyridinyl; 2-azatricyclo[3.3.1.1^3,7]dec-2-yloxidanyl; copper(l) chloride; In acetonitrile; at 20 ℃; for 7h; chemoselective reaction;

DOI:10.1002/anie.201309634

Reference yield: 81.0%

(-)-joubertinamine (74163-89-6) → (-)-mesembrine (468-53-1,6023-73-0,21104-37-0,24880-43-1,28639-24-9,35056-46-3,35056-47-4)

Guidance literature:

With manganese(IV) oxide; In benzene; at 20 - 24 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2008.10.048

Reference yield: 77.0%

Δ7-mesembrenone (35714-44-4) → (-)-mesembrine (468-53-1,6023-73-0,21104-37-0,24880-43-1,28639-24-9,35056-46-3,35056-47-4)

Guidance literature:

With lithium; In ammonia;

DOI:10.1016/S0040-4039(01)93019-9

upstream raw materials:

Δ7-mesembrenone

(3aR,7aS)-3a-(3,4-Dimethoxy-phenyl)-5-hydroxy-1-methyl-octahydro-indol-6-one

2,2-Dimethyl-propionic acid (3aR,7aS)-3a-(3,4-dimethoxy-phenyl)-1-methyl-6-oxo-octahydro-indol-5-yl ester

Acetic acid (3aR,7aS)-6-benzyloxy-3a-(3,4-dimethoxy-phenyl)-1-methyl-2,3,3a,4,5,7a-hexahydro-1H-indol-5-yl ester

Refernces

• 1、 Bokka, Apparao,Mao, James X.,Hartung, John,Martinez, Steven R.,Simanis, Justin A.,Nam, Kwangho,Jeon, Junha,Shen, Xiaoqiang. "Asymmetric Synthesis of Remote Quaternary Centers by Copper-Catalyzed Desymmetrization: An Enantioselective Total Synthesis of (+)-Mesembrine". supporting information. p. 5158 - 5162. Retrieved 2018/09/13.
• 2、 Spittler, Michael,Lutsenko, Kiril,Czekelius, Constantin. "Total Synthesis of (+)-Mesembrine Applying Asymmetric Gold Catalysis". . p. 6100 - 6105. Retrieved 2016/07/26.