CAS 357-70-0|Galantamine

Introduction：Basic information about CAS 357-70-0|Galantamine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Galantamine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	Galantamine
CAS Number	357-70-0	Molecular Weight	287.353
Density	1.3±0.1 g/cm3	Boiling Point	439.3±45.0 °C at 760 mmHg
Molecular Formula	C₁₇H₂₁NO₃	Melting Point	119-121ºC
MSDS	/	Flash Point	219.5±28.7 °C

Names

Name	galanthamine
Synonym	More Synonyms

Galantamine BiologicalActivity

Description	Galanthamine is a potent acetylcholinesterase (AChE) inhibitor with an IC50 of 500 nM.
Related Catalog	Signaling Pathways >>Neuronal Signaling >>AChEResearch Areas >>Neurological DiseaseNatural Products >>Others
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.

Chemical & Physical Properties

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
InChIKey	ASUTZQLVASHGKV-JDFRZJQESA-N
SMILES	COc1ccc2c3c1OC1CC(O)C=CC31CCN(C)C2
Storage condition	-20°C Freezer

Toxicological Information

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

Safety Information

Hazard Codes	Xi
HS Code	2942000000

Customs

HS Code	2942000000

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

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