Sanguinine
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Basic information
- CAS
60755-80-8- Standard SMILES
CN1CC[C@@]23C=C[C@H](O)C[C@@H]2Oc2c(O)ccc(c23)C1- InChIKey
OYSGWKOGUVOGFQ-RBOXIYTFSA-N- Molecular formula
- C16H19NO3
- Average molar mass
- 273.33 g/mol
- Monoisotopic mass
- 273.13649347
Overview
Sanguinine is a benzazepine.
Names & identifiers
- Preferred name
- Sanguinine
- IUPAC
- (1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene-9,14-diol
- English name
- O-DESMETHYLGALANTHAMINE
- Molecular formula
- C16H19NO3
- Molecular weight
- 273.33
Names & synonyms
Sanguinine60755-80-8O-DesmethylgalantamineL7ZOW3CZ7W(1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraene-9,14-diolDTXSID40209575(1S,12S,14R)-4-methyl-11-oxa-4-azatetracyclo(8.6.1.01,12.06,17)heptadeca-6(17),7,9,15-tetraene-9,14-diolRefChem:181161DTXCID90132066O-Desmethyl GalanthamineO-Desmethyl GalantamineO-DESMETHYLGALANTHAMINE
Show more names
O-DemethylgalantamineO-methyl-galanthamineGalantamine Impurity 7Galantamine Impurity 3O-Demethyl-galanthamine6-O-DemethylgalanthamineGalantamine O-Desmethyl Impurity
UNII-L7ZOW3CZ7WCHEMBL1524(4aS,6R,8aS)-11-Methyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-3,6-diol(4aS,6R,8aS)-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepine-3,6-diolGalantamine Impurity 66-O-demethylgalantamine(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepine-3,6-diolorb1296966
Database identifiers
- CAS
60755-80-8- PubChem CID
- 443722
- DTXSID
DTXSID40209575- ChEMBL
CHEMBL1524- ChEBI
CHEBI:32117- UNII
- L7ZOW3CZ7W
- Nikkaji
- J37.254D
Properties
Computed structural propertiesFilling in
- XLogP
- 1.5
- Topological polar surface area
- 52.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 426
Physicochemical properties
- Melting point
- 227 · 227-230°C (dec.)
- Boiling point
- 451.9 · 451.9±45.0 °C(Predicted)
- Density
- 1.37 · 1.37±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO: soluble
- form
- A solid
- pka
- 9.39 · 9.39±0.40(Predicted)
- color
- White to off-white
- CAS DataBase Reference
- 60755 · 60755-80-8
- FDA UNII
- 7 ZOW3CZ7W · L7ZOW3CZ7W
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H300
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites
O-Desmethylgalantamine has known human metabolites that include [(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-9-yl] hydrogen sulfate and (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[[(1S,12S,14R)-14-hydroxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-9-yl]oxy]oxane-2-carboxylic acid.
Applications
UsesA metabolite of Galanthamine, a selective acetylcholinesterase inhibitor
UsesA metabolite of Galanthamine (G188500), a selective acetylcholinesterase inhibitor.
UsesSanguinine 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.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Sanguinine is a benzazepine.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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