Epigalantamine

Base Information

• Chemical Name: Epigalantamine
• CAS No.: 1668-85-5
• Molecular Formula: C17H21 N O3
• Molecular Weight: 287.359
• European Community (EC) Number: 684-870-2
• UNII: P5ATS8V989
• DSSTox Substance ID: DTXSID50168189
• Nikkaji Number: J2.176.930D
• Wikidata: Q27286219
• Pharos Ligand ID: 9LKHGJ1J19PL
• Metabolomics Workbench ID: 123643
• ChEMBL ID: CHEMBL1565544
• Mol file: 1668-85-5.mol

Synonyms:Epigalantamine;Epi-Galantamine;1668-85-5;Epi-galanthamine;Epi Galanthamine;2-Epigalanthamine;UNII-P5ATS8V989;P5ATS8V989;(1S,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;(-)-Epigalanthamine;3-Epigalanthamine;6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6S,8aS)-;6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, (4AS,6S,8AS)-;Tocris-0686;2-EPI-GALANTHAMINE;SCHEMBL5359499;CHEMBL1565544;DTXSID50168189;GALANTAMINE METABOLITE M13;HY-N7265;SPH-1068;TNP00150;TNP00165;GALANTHAMINE, (3.ALPHA.)-;AKOS030241930;NCGC00017256-01;NCGC00017256-02;NCGC00017256-03;NCGC00024731-01;(4aS,6S,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol;CS-0111011;J-010315;Q27286219;GALANTAMINE HYDROBROMIDE IMPURITY B [EP IMPURITY];(1S,12S,14S)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0?,??.0?,??]heptadeca-6(17),7,9,15-tetraen-14-ol;(4AS,6S,8AS)-3-METHOXY-11-METHYL-5,6,9,10,11,12-HEXAHYDRO-4AH-(1)BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL

Chemical Property of Epigalantamine

Chemical Property:

• Vapor Pressure: 1.71E-08mmHg at 25°C
• Melting Point: 183-185°C
• Boiling Point: 439.3°C at 760 mmHg
• PKA: 13.93±0.20(Predicted)
• Flash Point: 219.5°C
• PSA: 41.93000
• Density: 1.28g/cm³
• LogP: 1.78820
• Storage Temp.: -20°C Freezer
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 287.15214353
• Heavy Atom Count: 21
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Epigalanthamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O
• Isomeric SMILES: CN1CC[C@@]23C=C[C@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O
• Uses: A selective acetylcholinesterase inhibitor.

Technology Process of Epigalantamine

There total 164 articles about Epigalantamine 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: 68.0%

(-)-narwedine (510-77-0,26601-10-5) → Galantamine hydrobromide (1953-04-4,98125-73-6,193146-85-9) + (-)-epigalanthamine (1668-85-5)

Guidance literature:

(-)-narwedine; With cerium(III) chloride heptahydrate; In methanol; dichloromethane; at -55 - -50 ℃; for 0.5h;

With sodium tetrahydroborate; In methanol; dichloromethane; at -55 - -50 ℃; for 2.5h; Temperature; diastereoselective reaction;

DOI:10.1016/j.tetasy.2013.11.016

Reference yield: 67.0%

2-[(4aS,9bS)-9-([([(1,1-dimethylethyl)oxy]carbonyl)(methyl)amino]methyl)-3-hydroxy-6-(methyloxy)-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-9-yl]ethyl methanesulfonate → (-)-epigalanthamine (1668-85-5) + Galantamine (357-70-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol070255i

Reference yield: 62.0%

propylamine (107-10-8,42939-71-9) + (1-formyl-7-hydroxy-4-methoxy-6,7-dihydro-5aH-dibenzofuran-9a-yl)acetonitrile → (-)-epigalanthamine (1668-85-5) + Galantamine (357-70-0)

Guidance literature:

propylamine; (1-formyl-7-hydroxy-4-methoxy-6,7-dihydro-5aH-dibenzofuran-9a-yl)acetonitrile; In methanol; at 20 ℃; for 8h;

With diisobutylaluminium hydride; In hexane; toluene; at -78 ℃;

With sodium dihydrogenphosphate; sodium cyanoborohydride; In methanol; at 20 ℃; for 8h;

DOI:10.1021/ja054449+

upstream raw materials:

(-)-narwedine

Galantamine

C₁₇H₁₈BrNO₄

propylamine

Downstream raw materials:

(4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one

10-benzyl-3α-hydroxy-6-methoxy-10-methyl-galantham-1-enium; chloride

3,4-didehydro-3-deoxygalanthamine

(-)-narwedine

Refernces

• 1、 Chaplin, David A.,Johnson, Nicholas B.,Paul, Jane M.,Potter, Gerard A.. "Dynamic diastereomeric salt resolution narwedine and its transformation to (-)-galanthamine". . p. 6777 - 6780. Retrieved 1998.
• 2、 Trinadhachari, Ganala Naga,Kamat, Anand Gopalkrishna,Prabahar, Koilpillai Joseph,Handa, Vijay Kumar,Srinu, Kukunuri Naga Venkata Satya,Babu, Korupolu Raghu,Sanasi, Paul Douglas. "Commercial scale process of galanthamine hydrobromide involving Luche reduction: Galanthamine process involving regioselective 1,2-reduction of α,β-unsaturated ketone". . p. 406 - 412. Retrieved 2013.
• 3、 Nugent, Jeremy,Banwell, Martin G.. "An Eleven-Step Synthesis of Galanthamine from Commercially Available Materials". . p. 5862 - 5867. Retrieved 2016.
• 4、 Trinadhachari, Ganala Naga,Kamat, Anand Gopalkrishna,Raghu Babu, Korupolu,Sanasi, Paul Douglas,Prabahar, Koilpillai Joseph. "Stereoselective syntheses of galanthamine and its stereoisomers by complementary Luche and L-selectride reductions". . p. 117 - 124. Retrieved 2014/02/14.