Galanthamine N-Oxide

Base Information

• Chemical Name: Galanthamine N-Oxide
• CAS No.: 134332-50-6
• Molecular Formula: C17H21NO4
• Molecular Weight: 303.35
• European Community (EC) Number: 682-869-1
• UNII: S6AF61T5WO
• DSSTox Substance ID: DTXSID40173681
• Nikkaji Number: J391.066K
• Wikidata: Q27288725
• Mol file: 134332-50-6.mol

Synonyms:Galanthamine N-Oxide;134332-50-6;Galantamine N-Oxide;199014-26-1;UNII-S6AF61T5WO;S6AF61T5WO;(1S,12S,14R)-9-methoxy-4-methyl-4-oxido-11-oxa-4-azoniatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;Galanthamine-N-oxide;SCHEMBL3299153;DTXSID40173681;GALANTHAMINE (RS)-N-OXIDE;LROQBKNDGTWXET-FVWDGWMTSA-N;GALANTAMINE METABOLITE M10;AKOS030241457;GALANTAMINE N-OXIDE [USP IMPURITY];Galanthamine 10-Oxide(Galanthamine N-Oxide);J-006516;Q27288725;(4AS-(4A.ALPHA.,6.BETA.,8AR*))-4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, N-OXIDE;6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, 11-OXIDE, (4AS,6R,8AS)-;6H-BENZOFURO(3A,3,2-EF)(2)BENZAZEPIN-6-OL, 4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-, 11-OXIDE, (4AS-(4A.ALPHA.,6.BETA.,8AR*))-

Chemical Property of Galanthamine N-Oxide

Chemical Property:

• Melting Point: 246-247°C
• PSA: 68.12000
• LogP: 1.82170
• Storage Temp.: -20°C Freezer
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 303.14705815
• Heavy Atom Count: 22
• Complexity: 483

Purity/Quality:

98%Min ^*data from raw suppliers

GalanthamineN-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1(CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O)[O-]
• Isomeric SMILES: C[N+]1(CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O)[O-]
• Uses: A metabolite of Galanthamine, a selective acetylcholinesterase inhibitor A metabolite of Galanthamine (G188500), a selective acetylcholinesterase inhibitor.

Technology Process of Galanthamine N-Oxide

There total 5 articles about Galanthamine N-Oxide 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: 94.0%

Galantamine (357-70-0) → galanthamine N-oxide (134332-50-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/S0960-894X(03)00397-4

Reference yield:

Galantamine (357-70-0) → galanthamine N-oxide (134332-50-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 ℃; for 1.5h;

DOI:10.1016/0031-9422(91)83751-6

Reference yield:

O-Demethylgalantamine (60755-80-8) → galanthamine N-oxide (134332-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 11 mg / MCPBA / CHCl₃ / 0.5 h / Ambient temperature

2: 2.7 mg / methanol; diethyl ether / 48 h / Ambient temperature

With 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; chloroform;

DOI:10.1016/0031-9422(91)83751-6

upstream raw materials:

diazomethane

sanguinine N-oxide

Galantamine

O-Demethylgalantamine

Downstream raw materials:

N-desmethyl galantamine

Refernces

• 1、 Kobayashi, Shigeru,Satoh, Kimihito,Numata, Atsushi,Shingu, Tetsuro,Kihara, Masaru. "ALKALOID N-OXIDES FROM LYCORIS SANGUINEA". . p. 675 - 677. Retrieved 1991.
• 2、 -. "METHOD FOR THE PRODUCTION OF HIGH-PURITY 4A, 5, 9, 10, 11, 12,-HEXAHYDRO-6H-BENZOFURO [3A, 3, 2-EF] [2] BENZAZEPINE, AND THE DERIVATIVES THEREOF". Page/Page column 8. . Retrieved 2010/05/13.