Basic information Safety Supplier Related

O-DESMETHYLGALANTHAMINE

Basic information Safety Supplier Related

O-DESMETHYLGALANTHAMINE Basic information

Product Name:
O-DESMETHYLGALANTHAMINE
Synonyms:
  • (4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-11-Methyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol
  • (4aS,8aS)-11-Methyl-4aα,5,9,10,11,12-hexahydro-6H-benzofuro[3a,3,2-ef][2]benzoazepine-3,6β-diol
  • (8aS)-5,6,9,10,11,12-Hexahydro-11-methyl-4aαH-benzofuro[3a,3,2-ef][2]benzazepine-3,6β-diol
  • 6-O-Demethylgalanthamine
  • 10-Methyl-galantham-1-ene-3b,6-diol
  • O-Demethyl-galanthamine
  • Sanguinine
  • 10-Methyl-galantham-1-ene-3,6-diol
CAS:
60755-80-8
MF:
C16H19NO3
MW:
273.33
Product Categories:
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Pharmaceuticals
Mol File:
60755-80-8.mol
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O-DESMETHYLGALANTHAMINE Chemical Properties

Melting point:
227-230°C (dec.)
Boiling point:
451.9±45.0 °C(Predicted)
Density 
1.37±0.1 g/cm3(Predicted)
storage temp. 
-20°C Freezer
solubility 
DMSO: soluble
form 
A solid
pka
9.39±0.40(Predicted)
CAS DataBase Reference
60755-80-8
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O-DESMETHYLGALANTHAMINE Usage And Synthesis

Chemical Properties

Pale Yellow Powder

Uses

A metabolite of Galanthamine, a selective acetylcholinesterase inhibitor

Uses

A metabolite of Galanthamine (G188500), a selective acetylcholinesterase inhibitor.

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.

Definition

ChEBI: Sanguinine is a benzazepine.

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