316189-74-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-1-pentyl-3-(4-Methoxynaphthoyl)indole is used as a cannabinoid receptor 2 agonist for its ability to selectively bind to and activate the CB2 receptor. This interaction is crucial for modulating various physiological processes and has been linked to potential therapeutic effects in treating a range of conditions, including inflammation, pain, and neurodegenerative diseases.
Used in Synthetic Cannabinoids:
As a derivative of indole-carbaldehyde, 2-Methyl-1-pentyl-3-(4-Methoxynaphthoyl)indole is also utilized in the development of synthetic cannabinoids. These compounds are designed to mimic the effects of naturally occurring cannabinoids found in the cannabis plant, offering an alternative for medical use and research. The synthetic nature of 2-Methyl-1-pentyl-3-(4-Methoxynaphthoyl)indole allows for greater control over its properties and potential applications, making it a valuable asset in the field of medicinal chemistry.

Upstream product

• 42951-36-0 2-methyl-1-pentylindole 
• 70696-57-0 4-methoxy-1-naphthoic acid chloride 
• 13041-62-8 4-methoxy-1-naphthoic acid 

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.