ChemicalBook--->CAS DataBase List--->69353-21-5

69353-21-5

69353-21-5 Structure

69353-21-5 Structure
IdentificationBack Directory
[Name]

GALANTHAMINE HYDROBROMIDE
[CAS]

69353-21-5
[Synonyms]

NIVALIN
1990/4/4
nivaline
NIVALIN, HBR
zocin-6-olhbr
GALANTAMINE HBR
GALANTHAMINE HBR
jilkonhydrobromide
Galantamine N-D3 HBr
Galantamine O-D3 HBr
lycoreminehydrobromide
GALANTAMINE HYDROBROMIDE
nivaline(pharmaceutical)
GALANTHAMIDE HYDROBROMIDE
galanthaminehydrogenbromide
nivaline(c17pharmaceutical)
Nootropics Power Galanthamine
GALANTHAMINE HYDROBROMIDE USP/EP/BP
Galantamine natural for system suitability
Galanthamine HBr (Galantamine Hydrobromide)
Galantamine synthetic for system suitability
Galanthamine, Hydrobromide - CAS 69353-21-5 - Calbiochem
High purity CAS 69353-21-5 GALANTHAMINE HYDROBROMIDE in stock
1,2,3,4,6,7,7a,11c-octahydro-9-methoxy-2-methyl-benzofuro(4,3,2-efg)(2)benza
3,2-efg)(2)benzazocin-6-ol,1,2,3,4,6,7,7a,11c-octahydro-9-methoxy-benzofuro(
1,2,3,4,6,7,7a,11c-Octahydro-9-methoxy-2-methylbenzofuro[4,3,2-efg]-2-benzazocin-6-ol hydrobromide
2,3,3a,8,9,10,11,11b-Octahydro-5-methoxy-9-methylbenzofuro[4,3,2-efg][2]benzazocin-2-ol hydrobromide
5-Methoxy-9-methyl-2,3,3a,3a1,8,9,10,11-octahydro-4-oxa-9-azacycloocta[def]fluoren-2-ol hydrobromide
4A,5,9,10,11,12-HEXAHYDRO-3-METHOXY-11-METHYL-6H-BENZOFURO[3A,3,2-EF][2]BENZAZEPIN-6-OL HYDROBROMIDE
Benzofuro[4,3,2-efg][2]benzazocin-2-ol,2,3,3a,8,9,10,11,11b-octahydro-5-Methoxy-9-Methyl-, hydrobroMide (9CI)
5-Methoxy-9-methyl-2,3,3a,3a1,8,9,10,11-octahydro-4-oxa-9-azacycloocta[def]fluoren-2-ol hydrobromide(Galantamine Hydrobromide)
Galantamine HydrobromideQ: What is Galantamine Hydrobromide Q: What is the CAS Number of Galantamine Hydrobromide Q: What is the storage condition of Galantamine Hydrobromide
[EINECS(EC#)]

217-780-5
[Molecular Formula]

C17H22BrNO3
[MDL Number]

MFCD00067672
[MOL File]

69353-21-5.mol
[Molecular Weight]

368.27
Chemical PropertiesBack Directory
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

ethanol: 1mg/mL
water: 1mg/mL
DMSO: 5mg/mL
[form ]

White solid
[color ]

white
[InChI]

InChI=1S/C17H21NO3.BrH/c1-18-6-5-10-7-12(19)8-14-15(10)16-11(9-18)3-4-13(20-2)17(16)21-14;/h3-4,7,12,14-15,19H,5-6,8-9H2,1-2H3;1H
[InChIKey]

DKGIHQCMWKXHHR-UHFFFAOYSA-N
[SMILES]

O(C1C=CC2CN(C)CCC3=CC(O)CC4C3C=2C=1O4)C.Br
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)
GHS06
[Signal word ]

Danger
[Hazard statements ]

H301
[Precautionary statements ]

P264-P270-P301+P310-P405-P501
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

45
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

DF8075000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[Storage Class]

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
[Hazard Classifications]

Acute Tox. 3 Oral
Questions And AnswerBack Directory
[Background]

Galantamine Hydrobromide is the hydrobromide salt form of galantamine, a tertiary alkaloid obtained synthetically or naturally from the bulbs and flowers of Narcissus and several other genera of the Amaryllidaceae family with anticholinesterase and neurocognitive-enhancing activities. Galantamine competitively and reversibly inhibits acetylcholinesterase, thereby increasing the concentration and enhancing the action of acetylcholine (Ach). In addition, galantamine is a ligand for nicotinic acetylcholine receptors, which may increase the presynaptic release of Ach and activate postsynaptic receptors. This agent may improve neurocognitive function in mild and moderate Alzheimer's disease and may reduce abstinence-induced cognitive symptoms that promote smoking relapse[1].
Hazard InformationBack Directory
[Uses]

A competitive and reversible inhibitor of acetylcholinesterase. Antimyasthenic agent. Can partially reverse the effects of scopolamine-induced amnesia in rats. Reported to improve learning and short-term memory in animal models.
Cholinesterase antagonist. Antimyasthenic agent. Can partially reverse the effects of scopolamine-induced amnesia in rats.
[General Description]

A competitive and reversible inhibitor of acetylcholinesterase. Antimyasthenic agent. Can partially reverse the effects of scopolamine-induced amnesia in rats. Reported to improve learning and short-term memory in animal models.
[Biological Activity]

Galantamine Hydrobromide (GH) is a plant phenanthridine alkaloid which is a selective and reversible acetylcholinesterase (AChE) inhibitor found in several members of the Amaryllidaceae family, such as snowdrops. GH has been approved for symptomatic treatment of AD and vascular dementia by oral or injectable administration. GH concentration-dependent inhibition of AChE activity has antioxidative properties, involving decreased superoxide anion and NO overproduction and restoring mitochondrial membrane potential. GH also possesses memory-enhancing effects via its action as a cholinesterase inhibitor, where it modulates muscarinic transmission, and it is also an allosteric potentiating ligand (APL) of nicotinic acetylcholine receptors (nAChRs). Recently, it was reported that GH potently inhibited delayed rectifier potassium currents, β-amyloid aggregation, and cytotoxicity. These properties contribute to its effectiveness in AD therapy. However, the pharmacological properties of GH administered orally or by injection would likely cause some side effects on the gastrointestinal tract and impact other tissues, organs, and systems outside the central nervous system (CNS) in AD treatment[1].
[Biochem/physiol Actions]

Primary TargetAcetylcholinesterase
[Clinical Use]

Galantamine, which was introduced in 2001, is an alkaloid found in plants of the family Amaryllidaceae, which includes the daffodil (Narcissus pseudonarcissus) and snowflake (Leucojum aestivum). It is a reversible inhibitor of AChE, but it does not appear to inhibit butyrylcholinesterase. Because it is a tertiary amine and can cross the blood-brain barrier, it is indicated for treatment of mild-to-moderate AD and dementia. It has been used outside the U.S. for more than 30 years as an anticurare agent in anesthesia. Galantamine differs from other cholinesterase inhibitors, because it allosterically binds to nicotinic receptors, giving it a dual cholinergic action.
[Metabolism]

It is metabolized (75%) by CYP2D6 and CYP3A4 to afford the normethyl, O-desmethyl, and O-desmethylnormethyl metabolites, along with some other minor metabolites. Unlike tacrine, galantamine is not associated with hepatotoxicity. Its elimination half-life is 5.7 hours.
[References]

[1] Weize Li . “Pharmacokinetic behavior and efficiency of acetylcholinesterase inhibition in rat brain after intranasal administration of galanthamine hydrobromide loaded flexible liposomes.” Environmental toxicology and pharmacology 34 2 (2012): Pages 272-279.
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