824960-02-3

Basic information

• Product Name: JWH-182
• Synonyms: JWH-182;1-PENTYL-3-(4-PROPYL-1-NAPHTHOYL)INDOLE
• CAS NO: 824960-02-3
• Molecular Formula: C27H29NO
• Molecular Weight: 383.52526
• Mol File: 824960-02-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: JWH-182(CAS DataBase Reference)
• NIST Chemistry Reference: JWH-182(824960-02-3)
• EPA Substance Registry System: JWH-182(824960-02-3)

Safety Data

• Hazardous Substances Data: 824960-02-3(Hazardous Substances Data)

Usage

Description

JWH-182 is a potent synthetic cannabinoid (CB) that selectively activates the central CB1 receptor with a Ki value of 0.65 nM and the peripheral CB2 receptor with a Ki value of 1.1 nM. Its effects in cells and animals are currently unknown.

Uses

Used in Pharmaceutical Research:
JWH-182 is used as a research compound for studying the effects and mechanisms of action of synthetic cannabinoids on the CB1 and CB2 receptors. This helps in understanding the potential therapeutic applications and side effects associated with these compounds.
Used in Drug Development:
JWH-182 serves as a lead compound in the development of new drugs targeting the CB1 and CB2 receptors. Its high affinity and selectivity for these receptors make it a valuable tool in designing more effective and safer medications for various conditions.
Used in Toxicological Studies:
JWH-182 is utilized in toxicological research to evaluate the safety and potential risks associated with synthetic cannabinoids. This helps in determining the appropriate dosages, administration routes, and potential side effects of these compounds in humans.
Note: The uses mentioned above are based on the general applications of synthetic cannabinoids and may not be specific to JWH-182. Further research and development are required to fully understand the potential uses and implications of JWH-182 in various industries.

Upstream product

• 59529-21-4 1-pentyl-1H-indole 
• 107777-22-0 4-propyl-1-naphthoic acid 

Relevant articles and documents

Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: Steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists

The synthesis and pharmacology of 47 1-alkyl-3-(1-naphthoyl)indoles (R = C3H7 and C5H11, R′ = H and CH3) is described. Naphthoyl substituents include 4- and 7-alkyl groups, plus 2, 4, 6, and 7-methoxy groups. Three of these compounds are highly selective CB2 receptor agonists. In an effort to improve indole-based CB2 cannabinoid receptor ligands and also to develop SAR for both the CB1 and CB2 receptors, 47 indole derivatives were prepared and their CB1 and CB2 receptor affinities were determined. The indole derivatives include 1-propyl- and 1-pentyl-3-(1- naphthoyl)indoles both with and without a 2-methyl substituent. Naphthoyl substituents include 4- and 7-alkyl groups as well as 2-, 4-, 6-, 7-methoxy and 4-ethoxy groups. The effects of these substituents on receptor affinities are discussed and structure-activity relationships are presented. In the course of this work three new highly selective CB2 receptor agonists were identified, 1-propyl-3-(4-methyl-1-naphthoylindole (JWH-120), 1-propyl-2-methyl-3-(6-methoxy-1-naphthoylindole (JWH-151), and 1-pentyl-3-(2-methoxy-1-naphthoylindole (JWH-267). GTPγS assays indicated that JWH-151 is a full agonist at CB2, while JWH-120 and JWH-267 are partial agonists. Molecular modeling and receptor docking studies were carried out on a set of 3-(4-propyl-1-naphthoyl)indoles, a set of 3-(6-methoxy-1- naphthoyl)indoles and the pair of N-pentyl-3-(2-methoxy-1-naphthoyl)indoles. Docking studies indicated that the CB1 receptor affinities of these compounds were consistent with their aromatic stacking interactions in the aromatic microdomain of the CB1 receptor.