3891-74-5

Basic information

• Product Name: (4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide
• CAS NO: 3891-74-5
• Molecular Formula: C₁₈H₂₄NO₃*I
• Molecular Weight: 429.2925
• Mol File: 3891-74-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide(3891-74-5)
• EPA Substance Registry System: (4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide(3891-74-5)

Safety Data

• Hazardous Substances Data: 3891-74-5(Hazardous Substances Data)

Usage

Description

(4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide is a complex organic compound that features a benzofuran and a benzazepine ring system. It is characterized by the presence of a hydroxy and a methoxy group, along with a quaternary ammonium moiety. The molecule has three stereocenters, which confer a specific stereochemistry to it. As an iodide salt, the iodine atom bears a positive charge. (4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide may possess pharmacological properties, and its intricate structure indicates potential applications in medicinal chemistry research and drug development.

Uses

Used in Medicinal Chemistry Research:
(4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide is utilized as a research compound for exploring its potential pharmacological activity. Its unique structure and functional groups make it a candidate for studying various biological interactions and mechanisms.
Used in Drug Development:
In the pharmaceutical industry, (4aS,6R)-6-hydroxy-3-methoxy-11,11-dimethyl-5,6,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepin-11-ium iodide serves as a key component in the development of new drugs. Its complex structure allows for the fine-tuning of pharmacokinetic and pharmacodynamic properties, which is essential for creating effective and safe medications.

Upstream product

• 74-88-4 methyl iodide 
• 357-70-0 Galantamine 

Downstream Products

• 357-70-0 Galantamine 

Relevant articles and documents

Synthesis and evaluation of tritium labelled 10-methylgalanthamine iodide: A novel compound to examine the mechanism of interaction of galanthamine derivatives with the nicotinic acetylcholine receptors

A new promising galanthamine derivative, 10-[ 3H]methylgalanthamine iodide, was synthesized for binding studies to nicotinic acetylcholine receptors expressed in Torpedo electric ray electroplaques. Galanthamine was reacted with [3H]methyl iodide to yield 10-[3H]methylgalanthamine iodide with a radiochemical yield of > 70% and a specific activity of 32 Ci/mmol after purification via solid phase extraction. To test the ligand properties of the radioligand, calcium imaging and electrophysiology of the non-radioactive analogue were performed to obtain an EC50 of 270 nM, a Hill coefficient of 1.9 and the induced cell current. Copyright

Chemical and pharmacological characterization of galanthamine, an acetylcholinesterase inhibitor, and its derivatives. A potential application in Alzheimer's disease ?

We conducted structural and pharmacological studies of galanthamine, a cortical acetylcholinesterase (AChE) inhibitor, and 19 structural analogs.Systematic derivatization of galanthamine at the cyclohexene ring, tertialy amino, hydroxyl, methoxyl functions indicated that these structural features are essential for biological activity.Molecular modeling studies suggested that the low energy conformations of the analogs are similar to that of the parent.One derivative, galanthamine n-butyl carbamate, had an LD50 of over 100 mg/kg (ip) in mice.In a passive avoidanceparadigm, this analog improved performance in a dose-dependant fashion with a peak effect at 0.1 mg/kg in control and 0.5 mg/kg in basal forebrain lesioned mice.In the same paradigm, the peak effect of the parent compound is a 6-fold higher dose.With this surprisingly high therapeutic ratio, this compound may be of interest in treating cholinergic deficits of the central nervous system such as Alzheimer's desease. galanthamine derivatives / molecular modeling / avetylcholinesterase inhibitor / Alzheimer's desease / passive avoidance / basal forebrain lesion