69353-21-5

Basic information

• Product Name: GALANTHAMINE HYDROBROMIDE
• Synonyms: 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(;galanthaminehydrogenbromide;jilkonhydrobromide;lycoreminehydrobromide;nivaline;nivaline(c17pharmaceutical);nivaline(pharmaceutical)
• CAS NO: 69353-21-5
• Molecular Formula: C17H22BrNO3
• Molecular Weight: 368.27
• EINECS: 217-780-5
• Product Categories: Galantamine
• Mol File: 69353-21-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 630.4 °C at 760 mmHg
• Flash Point: 335 °C
• Appearance: /
• Density: 1.593 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: −20°C
• CAS DataBase Reference: GALANTHAMINE HYDROBROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GALANTHAMINE HYDROBROMIDE(69353-21-5)
• EPA Substance Registry System: GALANTHAMINE HYDROBROMIDE(69353-21-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DF8075000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 69353-21-5(Hazardous Substances Data)

Usage

Description

Galanthamine Hydrobromide is a naturally occurring alkaloid compound that acts as a competitive and reversible inhibitor of acetylcholinesterase. It is an anti-myasthenic agent known for its ability to partially reverse the effects of scopolamine-induced amnesia in rats. Galanthamine Hydrobromide has also been reported to improve learning and short-term memory in animal models.

Uses

Used in Pharmaceutical Industry:
Galanthamine Hydrobromide is used as a therapeutic agent for the treatment of Alzheimer's disease and other cognitive disorders. It works by inhibiting the enzyme acetylcholinesterase, which helps to increase the levels of acetylcholine in the brain, thereby improving cognitive function and memory.
Used in Research Applications:
Galanthamine Hydrobromide is used as a research tool in the study of acetylcholinesterase inhibition and its effects on learning and memory. It is also used to investigate the mechanisms underlying Alzheimer's disease and other cognitive disorders.
Used in Drug Development:
Galanthamine Hydrobromide serves as a lead compound in the development of new drugs targeting acetylcholinesterase inhibition for the treatment of cognitive disorders and Alzheimer's disease. Its structure and properties provide valuable insights for the design and synthesis of novel therapeutic agents with improved efficacy and safety profiles.

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.

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