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357-70-0

357-70-0 structure
357-70-0 structure
  • Name: Galantamine
  • Chemical Name: galanthamine
  • CAS Number: 357-70-0
  • Molecular Formula: C17H21NO3
  • Molecular Weight: 287.353
  • Catalog: Biochemical Natural product
  • Create Date: 2018-07-01 20:29:12
  • Modify Date: 2025-08-20 12:52:05
  • Galanthamine is a potent acetylcholinesterase (AChE) inhibitor with an IC50 of 500 nM.
Name galanthamine
Synonyms MFCD00867189
3,4-Dihydrogalanthamine
Galantamine
Nivalin
6H-Benzofuro[3a,3,2-ef][2]benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, (4aS,6R,8aS)-
Lycoremine
Galantamine Hydrobromide
(4aS,6R,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol
Galanthamine
Description Galanthamine is a potent acetylcholinesterase (AChE) inhibitor with an IC50 of 500 nM.
Related Catalog
Target

IC50: 0.5 μM (AChE)[1]

In Vitro Galanthamine inhibits AChE and BChE with IC50 of 0.5 and 8.5 μM[1]. Galanthamine acts as a positive allosteric modulator (PAM) of human α4β2 AChRs expressed in permanently transfected HEK 293 cells. Galanthamine increases the response of (α4β2)2α5 AChRs to 1 μM ACh by up to 220% with very low concerntration(EC50=0.25 nM). Only small potentiation (20%) of either α4β2 or (α4β2)2β3 AChRs is detected using FLEXstation assays. Galanthamine at concentrations of 1 μM and above inhibits all three AChR subtypes[2].
In Vivo Acute administration of Galantamine (0.3-3 mg/kg, i.p.) increases IGF2 mRNA levels in the hippocampus, but not in the prefrontal cortex, in time- and dose-dependent manner. Galantamine (3 mg/kg, i.p.) causes a transient increase in fibroblast growth factor 2 mRNA levels and a decrease in brain-derived neurotrophic factor mRNA levels in the hippocampus, while it does not affect the mRNA levels of other neurotrophic/growth factors. The Galantamine-induced increase in the hippocampal IGF2 mRNA levels is blocked by Mecamylamine, a nonselective nicotinic acetylcholine (ACh) receptor (nAChR) antagonist, and Methyllycaconitine, a selective α7 nAChR antagonist, but not by Telenzepine, a preferential M1muscarinic ACh receptor antagonist. Moreover, the selective α7 nAChR agonist PHA-543613 increasea the IGF2 mRNA levels, while Donepezil, an acetylcholinesterase inhibitor, does not. Galantamine also increases hippocampal IGF2 protein, which is blocked by Methyllycaconitine[2].
Animal Admin Mice[2] Eight-week-old male ddY mice are housed in cages (24 cm×17 cm×12 cm) in each group of five to six animals under controlled environmental conditions (22±1°C; 12:12-h light-dark cycle, lights on at 0800 hours, food and water ad libitum) for 1 week before use in the experiments. 453 mice are used in total and in single use for each purpose. The following drugs are used: mecamylamine, methyllycaconitine, oxotremorine, and telenzepine, and Galantamine, Donepezil, and PHA-543613. All drugs are dissolved in saline (0.9 % solution of NaCl). Drugs are administered in a volume of 10 mL/kg intraperitoneally (i.p.) (Galantamine, Donepezil, Mecamylamine, Methyllycaconitine, Oxotremorine) or subcutaneously (s.c.) (PHA-543613, Telenzepine).
References

[1]. Melanie-Jayne R. Howes, et al. Acetylcholinesterase inhibitors of natural origin. International Journal of Research in Pharmaceutical and Biomedical Sciences 3(SI 1):67-86.

[2]. Kuryatov A, et al. Roles of accessory subunits in alpha4beta2(*) nicotinic receptors. Mol Pharmacol. 2008 Jul;74(1):132-43.

[3]. Kita Y, et al. Galantamine increases hippocampal insulin-like growth factor 2 expression via α7 nicotinic acetylcholine receptors in mice. Psychopharmacology (Berl). 2013 Feb;225(3):543-51.
Density 1.3±0.1 g/cm3
Boiling Point 439.3±45.0 °C at 760 mmHg
Melting Point 119-121ºC
Molecular Formula C17H21NO3
Molecular Weight 287.353
Flash Point 219.5±28.7 °C
Exact Mass 287.152130
PSA 41.93000
LogP 1.75
Vapour Pressure 0.0±1.1 mmHg at 25°C
Index of Refraction 1.636
Storage condition -20°C Freezer

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LW5952100
CHEMICAL NAME :
Galanthamine
CAS REGISTRY NUMBER :
357-70-0
BEILSTEIN REFERENCE NO. :
0093736
LAST UPDATED :
199706
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C17-H21-N-O3
MOLECULAR WEIGHT :
287.39

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22900 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 37,689,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4550113
Hazard Codes Xi
HS Code 2942000000
HS Code 2942000000
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