3891-74-5

Usage

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 academic research and scientific papers

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

Synthesis and stereoselective dealkylation of N-chiral quarternary N-alkyl galanthaminium halides

The synthesis of N-chiral galanthaminium halides and their stereoselective dealkylation is described. The stereochemistry of two key compounds was determined by X-ray structure analysis.

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

Spectroscopic studies of galanthamine and galanthamine methiodide

Structural studies of the alkaloid galanthamine 1 and its salt, galanthamine methiodide 2, were carried out both in solution and in the solid state, using spectroscopic methods (UV, IR, 1H NMR, 13C NMR and X-ray analysis).Several one- and two-dimensional techniques were used to assign the 1H NMR and 13C NMR spectra of 1.The types of hydrogen bonding exhibited by 1 and 2, in solution and in the solid state, were investigated.Keywords: galanthamine / galanthamine methiodide / spectral studies / hydrogen bonding