CasNo: 1953-04-4
Molecular Formula: C17H21NO3.HBr
Appearance: white to offf-white powder
Outline |
Galantamine hydrobromide also called as 11-methyl-3-methoxy-4a, 5, 9, 10, 11, 12-hexahydro-6H-benzene and furan [3a, 3, 2-ef] [2] benzazepine-6-ol hydrobromide, is an alkaloid isolated from Lycoris plants. In the 1960 s, China had first successfully isolated it from domestic Medicago Lycoris and Lycoris radiata, and had recorded into the Chinese Pharmacopoeia in 1977. This kind of herbal medicine has already had a history of 30 years of clinical application in some countries and regions for the treatment of reversal neuromuscular blockade, myasthenia gravis, and children with cerebral palsy psychosis. |
Physical and Chemical Properties |
It is white crystalline powder and is odorless with bitter taste. Galanthamine can be solubilized hot water, chloroform, acetone, and alcohol. However, it is less soluble in ether and benzene. |
Indications |
One example of drug that possesses cholinesterase inhibition activity is Galantamine hydrobromide (GH). It is suitable for treatment of benign memory disorders, improving the directed memory, associative learning, image memory, nonsense figure recognition and also portraits recalling capability of the patients. |
Uses |
Galantamine hydrobromide (GH) is the hydrobromide salt form of galanthamine. It is the major bioactive compound that is widely used in the treatment of neurological disorders, including Alzheimer's disease. |
Chemical Properties |
Galantamine hydrobromide is a white to almost white powder and is sparingly soluble in water. |
General Description |
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.Galantamine Hydrobromide, a reversible, competitive acetyl cholinesterase inhibitor, is suggested for the remedy of mild to moderate dementia of the Alzheimer′s type. |
Biological Activity |
Long-acting, centrally active acetylcholinesterase inhibitor (IC 50 = 410 nM) and allosteric potentiator at neuronal nicotinic ACh receptors. Prevents β -amyloid-induced apoptosis in SH-SY5Y and bovine chromaffin cells. Long-term administration reduces amyloid precursor protein deposition and neurodegeneration in a mouse model of Alzheimer's disease. |
InChI:InChI=1/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/p+1/t12-,14-,17-/m0/s1
Galanthamine in the leaves was also improved with 8 g/L NaCl. Salt stress treatments did not change the lycorine content in the leaves.
The invention concerns a method for prep...
Effect of lanthanide chloride in the Luc...
(-)-narwedine
Galantamine hydrobromide
Conditions | Yield |
---|---|
(-)-narwedine; With L-Selectride; In tetrahydrofuran; for 3.5h; Inert atmosphere; Large scale;
With hydrogen bromide; In tetrahydrofuran; ethanol; at 20 ℃; for 0.5h; Large scale;
|
99% |
(-)-narwedine; With L-Selectride; In tetrahydrofuran; at -50 - -45 ℃; for 4h;
With hydrogen bromide; In ethanol; water; at 15 - 20 ℃; for 2h; diastereoselective reaction;
|
85.4% |
With hydrogen bromide; L-Selectride; Yield given. Multistep reaction;
|
|
(-)-narwedine; With L-Selectride; In tetrahydrofuran; at -15 - 20 ℃; for 1.5h;
With hydrogen bromide; In tetrahydrofuran; at 0 - 20 ℃; for 1h;
|
(-)-narwedine
Galantamine hydrobromide
(-)-epigalanthamine
Conditions | Yield |
---|---|
(-)-narwedine; With cerium(III) chloride heptahydrate; In methanol; dichloromethane; at -55 - -50 ℃; for 0.5h;
With sodium tetrahydroborate; In methanol; dichloromethane; at -55 - -50 ℃; for 2.5h; Temperature; diastereoselective reaction;
|
68% 0.14% |
(-)-narwedine
(-)4a,5,9,10,11,12-hexhydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-one
galantamine
(-)-galantamine tartarate
(-)-(4aα,6β)-6-chloro-4a-5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-e,f][2]benzazepin
O-Demethylgalantamine
N-desmethyl galantamine
GLN-1062
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