Galanthamine, cholinesterase inhibitor

Key facts

CAS number

357-70-0

Form

Solid

form

Molecular weight

287.35 Da

Molecular formula

C₁₇H₂₁NO₃

PubChem

9651

Nature

Synthetic

Solubility

Soluble in DMSO to 50 mM

Soluble in ethanol to 100 mM with gentle warming

Biochemical name

Galantamine

Biological description

Potent selective acetylcholinesterase inhibitor (IC₅₀ = 410 nM). Greater than 50-fold selective versus butyrylcholinesterase. Inhibits RBC cholinesterase activity 10-fold more potently than that of human brain tissue. Reduces apoptotic effect of thapsigargin in SH-SY5Y cells. Non-competitive nicotinic receptor aganist in rat PC12 cells. Neuroprotective following ischemia-reperfusion injury in animal models.

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

InChi

InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1

InChiKey

ASUTZQLVASHGKV-JDFRZJQESA-N

IUPAC Name

(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol