(-)-Mesembrine

Base Information

• Chemical Name: (-)-Mesembrine
• CAS No.: 24880-43-1
• Molecular Formula: C₁₇H₂₃NO₃
• Molecular Weight: 289.375
• UNII: 86E2ZU4ETY,423182RCI5
• DSSTox Substance ID: DTXSID50947774
• Nikkaji Number: J17.690G
• Wikipedia: Mesembrine
• Wikidata: Q56450441
• Metabolomics Workbench ID: 68488
• ChEMBL ID: CHEMBL2008762
• Mol file: 24880-43-1.mol

Synonyms:mesembrine

Chemical Property of (-)-Mesembrine

Chemical Property:

• Vapor Pressure: 3.09E-07mmHg at 25°C
• Boiling Point: 419.2°Cat760mmHg
• PKA: 8.78±0.40(Predicted)
• Flash Point: 207.3°C
• PSA: 38.77000
• Density: 1.133g/cm³
• LogP: 2.33660
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 289.16779360
• Heavy Atom Count: 21
• Complexity: 400

Purity/Quality:

99%, ^*data from raw suppliers

Mesembrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
• Isomeric SMILES: CN1CC[C@]2([C@@H]1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
• Uses: Mesembrine is 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 129 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、 Wang, Lu-Ning,Cui, Qi,Yu, Zhi-Xiang. "A Concise Total Synthesis of (-)-Mesembrine". . p. 10165 - 10171. Retrieved 2016/11/17.
• 2、 Ilardi, Elizabeth A.,Isaacman, Michael J.,Qin, Ying-chuan,Shelly, Sommer A.,Zakarian, Armen. "Consecutive sigmatropic rearrangements in the enantioselective total synthesis of (-)-joubertinamine and (-)-mesembrine". experimental part. p. 3261 - 3269. Retrieved 2009/08/15.