JWH-360

JWH-360

IUPAC Name:	(6aR,10aR)-3-(1-naphthylmethyl)-1,2,3,6,6a,7,10,10a-octahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran
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Chemical formula	CHNO
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JWH-360 is a synthetic cannabinoid compound from the naphthoylindole family. It was developed by the chemist John W. Huffman and is known for its high affinity for the CB2 receptor, which is part of the endocannabinoid system.

Chemical Structure and Properties

JWH-360 is characterized by its complex chemical structure, which includes a naphthyl group attached to a dibenzopyran ring system. The compound has a molecular formula of C₂₆H₃₀O and a molar mass of 358.52 g/mol. The stereochemistry of JWH-360 is defined by its specific configuration, which is crucial for its activity at cannabinoid receptors.

Pharmacology

JWH-360 acts as a potent agonist at the CB2 receptor, with a high selectivity over the CB1 receptor. This selectivity makes it of interest for research into therapeutic applications that target the CB2 receptor, which is primarily expressed in the peripheral tissues and is involved in modulating immune responses and inflammation.

Receptor Binding

The binding affinity of JWH-360 for the CB2 receptor is significantly higher than for the CB1 receptor, which is predominantly found in the central nervous system. This selective binding profile suggests potential uses in treating conditions such as chronic pain, inflammation, and autoimmune diseases without the psychoactive effects associated with CB1 receptor activation.

Synthesis

The synthesis of JWH-360 involves the condensation of a naphthylmethyl group with a dibenzopyran core. The process requires precise control of reaction conditions to ensure the correct stereochemistry is achieved, which is essential for its biological activity.

Legal Status

As with many synthetic cannabinoids, the legal status of JWH-360 varies by country. In some jurisdictions, it may be classified as a controlled substance due to its potential for abuse and lack of medical approval.

Research and Applications

Research into JWH-360 and similar compounds is ongoing, with studies focusing on their potential therapeutic benefits and mechanisms of action. The selective CB2 receptor activity of JWH-360 makes it a candidate for further investigation in the context of pain management, neuroprotection, and immune modulation.

Safety and Toxicology

The safety profile of JWH-360 has not been extensively studied in humans. However, as with other synthetic cannabinoids, there is a potential for adverse effects, particularly if used inappropriately or in high doses. Research is needed to fully understand its toxicological properties and potential risks.

Also see

• Synthetic cannabinoids
• CB2 receptor
• John W. Huffman
• Endocannabinoid system