1366068-04-3

Basic information

• Product Name: JWH 424
• Synonyms: JWH 424;(8-bromonaphthalen-1-yl)-(1-pentylindol-3-yl)methanone
• CAS NO: 1366068-04-3
• Molecular Formula: C24H22BrNO
• Molecular Weight: 420.34158
• Mol File: 1366068-04-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: JWH 424(CAS DataBase Reference)
• NIST Chemistry Reference: JWH 424(1366068-04-3)
• EPA Substance Registry System: JWH 424(1366068-04-3)

Safety Data

• Hazardous Substances Data: 1366068-04-3(Hazardous Substances Data)

Usage

General Description

JWH 424 is a synthetic cannabinoid that acts as a potent agonist at the cannabinoid receptors CB1 and CB2. It produces effects similar to those of THC, the main psychoactive component of cannabis, including relaxation, euphoria, and altered perception of time and space. However, JWH 424 is much more potent than THC, with a lower effective dose, and it can also have more intense and longer-lasting effects. Because of these properties, JWH 424 has been associated with a higher risk of adverse reactions and potentially dangerous physical and psychological effects, leading to its classification as a controlled substance in many jurisdictions.

Upstream product

• 6314-27-8 O-(hydroxymercuri)-1-naphtoic acid anhydride 
• 1729-99-3 8-bromonaphthalene-1-carboxylic acid 
• 59529-21-4 1-pentyl-1H-indole 
• 56268-44-1 8-bromo-1-naphthoyl chloride 

Relevant articles and documents

Synthesis and pharmacology of 1-alkyl-3-(1-naphthoyl)indoles: Steric and electronic effects of 4- and 8-halogenated naphthoyl substituents

To develop SAR at both the cannabinoid CB1 and CB2 receptors for 3-(1-naphthoyl)indoles bearing moderately electron withdrawing substituents at C-4 of the naphthoyl moiety, 1-propyl and 1-pentyl-3-(4-fluoro, chloro, bromo and iodo-1-naphthoyl) derivatives were prepared. To study the steric and electronic effects of substituents at the 8-position of the naphthoyl group, the 3-(4-chloro, bromo and iodo-1-naphthoyl)indoles were also synthesized. The affinities of both groups of compounds for the CB1 and CB2 receptors were determined and several of them were evaluated in vivo in the mouse. The effects of these substituents on receptor affinities and in vivo activity are discussed and structure-activity relationships are presented. Although many of these compounds are selective for the CB2 receptor, only three JWH-423, 1-propyl-3-(4-iodo-1-naphthoyl)indole, JWH-422, 2-methyl-1-propyl-3-(4-iodo-1-naphthoyl)indole, the 2-methyl analog of JWH-423 and JWH-417, 1-pentyl-3-(8-iodo-1-naphthoyl)indole, possess the desirable combination of low CB1 affinity and good CB2 affinity.