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Usage

Uses

Used in Pharmaceutical Industry:
Methanone, (4-methoxy-1-naphthalenyl)[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]is used as a synthetic cannabinoid for the development of drugs targeting the CB1 receptor. Its high affinity for the receptor makes it a promising candidate for the treatment of various conditions, such as pain, inflammation, and neurological disorders.
Used in Research Applications:
In the field of research, Methanone, (4-methoxy-1-naphthalenyl)[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]is used as a research tool to study the effects and mechanisms of action of cannabinoids on the CB1 receptor. This helps scientists to better understand the role of the endocannabinoid system in various physiological and pathological processes, and to develop new therapeutic strategies.
Used in Drug Design and Development:
Methanone, (4-methoxy-1-naphthalenyl)[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]can be used as a starting point for the design and development of new drugs with improved pharmacological properties. By modifying its chemical structure, researchers can potentially create compounds with higher selectivity, potency, and reduced side effects, making them more suitable for clinical use.

Upstream product

• 13041-62-8 4-methoxy-1-naphthoic acid 
• 70696-57-0 4-methoxy-1-naphthoic acid chloride 
• 72395-48-3 1-<2-(4-morpholinyl)ethyl>-1H-indole 

Relevant academic research and scientific papers

3-Indolyl-1-naphthylmethanes: New cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor

A series of 1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (9-11) and 2-methyl-1-pentyl-1H-indol-3-yl-(1-naphthyl)methanes (12-14) have been synthesized to investigate the hypothesis that cannabimimetic 3-(1-naphthoyl)indoles interact with the CB1 receptor by hydrogen bonding to the carbonyl group. Indoles 9-11 have significant (Ki=17-23 nM) receptor affinity, somewhat less than that of the corresponding naphthoylindoles (5, 15, 16). 2-Methyl-1-indoles 12-14 have little affinity for the CB1 receptor, in contrast to 2-methyl-3-(1-naphthoyl)indoles 17-19, which have affinities comparable to those of 5, 15, 16. A cannabimimetic indene hydrocarbon (26) was synthesized and found to have Ki=26±4 nM. Molecular modeling and receptor docking studies of naphthoylindole 16, its 2-methyl congener (19) and indolyl-1-naphthylmethanes 11 and 14, combined with the receptor affinities of these cannabimimetic indoles, strongly suggest that these cannabinoid receptor ligands bind primarily by aromatic stacking interactions in the transmembrane helix 3-4-5-6 region of the CB1 receptor.

Aminoalkylindoles: Structure - Activity Relationships of Novel Cannabinoid Mimetics

Aminoalkylindoles (AAIs) are a novel series of cannabinoid receptor ligands.In this report we disclose the structural features of AAIs which are important for binding to this receptor as measured by inhibition of binding of 3H>Win 55212-2 (5).Functional activity in the mouse vas deferens is also noted and used to distinguish agonists from potential antagonists.The key structural features for potent cannabinoid activity in this series are a bicyclic (naphthyl) substituent at the 3-position, a small (H) substituent at the 2-position, and an aminoethyl (morpholinoethyl) substituent at the 1-position.A 6-bromo analog, Win 54461 (31), has been identified as a potential cannabinoid receptor antagonist.Modeling experiments were done to develop a pharmacophore and also to compare AAI structures with those of classical cannabinoids.The fact that the cannabinoid AAIs arose out of work on a series of cyclooxygenase inhibitors makes sense now that an endogenous cannabinoid ligand has been identified which is a derivative of arachidonic acid.Because of their unique structures and physical properties, AAIs provide useful tools to study the structure and function of the cannabinoid receptor(s).