Sanguinine

Base Information

• Chemical Name: Sanguinine
• CAS No.: 60755-80-8
• Molecular Formula: C16H19 N O3
• Molecular Weight: 273.332
• UNII: L7ZOW3CZ7W
• DSSTox Substance ID: DTXSID40209575
• Nikkaji Number: J37.254D
• Wikidata: Q27114789
• Pharos Ligand ID: LWLLGK79QCUQ
• Metabolomics Workbench ID: 69842
• ChEMBL ID: CHEMBL1524
• Mol file: 60755-80-8.mol

Synonyms:sanguinine

Chemical Property of Sanguinine

Chemical Property:

• Appearance/Colour: Pale Yellow Powder
• Vapor Pressure: 5.91E-09mmHg at 25°C
• Melting Point: 227-230°C (dec.)
• Boiling Point: 451.9°C at 760 mmHg
• Flash Point: 227.1°C
• PSA: 52.93000
• Density: 1.37g/cm³
• LogP: 1.48520
• Storage Temp.: -20°C Freezer
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 273.13649347
• Heavy Atom Count: 20
• Complexity: 426

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

O-DesmethylGalanthamine ^*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)O)O
• Isomeric SMILES: CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)O)O
• Uses: Sanguinine has a more potent acetylcholinesterase inhibitory activity than galanthamine due to an extra hydroxyl group available for potential interaction with acetylcholinesterase. Sanguinine, in turn, is 10-fold more selective than galanthamine for acetylcholinesterase (AChE) vs. butyrylcholinesterase (BuChE). The lack of AChE inhibitory activity of lycoramine and epinorlicoramine could be due to the occurrence of a double bond in ring C, which does not allow these alkaloids to have the same spatial configuration as the active alkaloids of this series.

Technology Process of Sanguinine

There total 2 articles about Sanguinine 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: 98.0%

Galantamine hydrobromide (1953-04-4,98125-73-6,193146-85-9) → O-Demethylgalantamine (60755-80-8)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at 65 ℃; for 24h;

DOI:10.1002/jlcr.1510

Reference yield: 95.0%

Galantamine (357-70-0) → O-Demethylgalantamine (60755-80-8)

Guidance literature:

With L-Selectride; In tetrahydrofuran; for 20h; Heating;

DOI:10.1016/S0968-0896(98)00133-3

Reference yield: 36.0%

O-Demethylgalantamine (60755-80-8) + [13C,2H4]methyl alcohol (32479-98-4) → C16(13)CH18(2)H3NO3

Guidance literature:

With di-isopropyl azodicarboxylate; Ph₃P-resin; In tetrahydrofuran; at 20 ℃; for 20h;

upstream raw materials:

Galantamine

Galantamine hydrobromide

Downstream raw materials:

Galantamine

galanthamine N-oxide

Refernces

• 1、 Schildan, A.,Schirrmacher, R.,Samochocki, M.,Christner, C.,Mmaelicke, A.,Roesch, F.. "Synthesis and in vitro evaluation of galanthamine derivatives for examination of nicotinic acetylcholine receptor system". . p. S247 - S249. Retrieved 2007/10/03.
• 2、 Han, SY,Sweeney, JE,Bachman, ES,Schweiger, EJ,Forloni, G,et al.. "Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease ?". . p. 673 - 687. Retrieved 2007/10/02.