JWH-315

Synthetic cannabinoid

CaptionSynonyms

JWH-315

Drug Information
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Identifiers ATC Code DrugBank KEGG ChEBI ChEMBL		Chemical Data Molecular Weight

JWH-315 is a synthetic cannabinoid that acts as a potent agonist at the cannabinoid receptors. It is part of the naphthoylindole family of compounds, which are known for their ability to mimic the effects of tetrahydrocannabinol (THC), the primary psychoactive component of cannabis.

Chemical Structure and Properties

JWH-315 is chemically classified as a naphthoylindole, with the systematic IUPAC name: (1-(2-(4-(1,1-dimethylheptyl)phenyl)ethyl)pyrrolidin-2-ylidene)(naphthalen-1-yl)methanone. The compound has a molecular formula of C₂₈H₃₅NO and a molecular weight of 401.59 g/mol.

The structure of JWH-315 includes a naphthalene group, a pyrrolidine ring, and a dimethylheptyl side chain, which contribute to its high affinity for cannabinoid receptors. The presence of the dimethylheptyl group is particularly significant, as it enhances the lipophilicity of the compound, allowing it to cross the blood-brain barrier more effectively.

Pharmacology

JWH-315 is a full agonist at the CB₁ and CB₂ cannabinoid receptors, with a higher affinity for the CB₂ receptor. This selectivity makes it of interest for research into the therapeutic potential of CB₂ receptor agonists, which are thought to have anti-inflammatory and analgesic properties without the psychoactive effects associated with CB₁ receptor activation.

Synthesis

The synthesis of JWH-315 involves the reaction of 1-naphthoyl chloride with 1-(2-(4-(1,1-dimethylheptyl)phenyl)ethyl)pyrrolidine. This process typically requires the use of an organic solvent and a base to facilitate the reaction, followed by purification steps to isolate the desired product.

Legal Status

The legal status of JWH-315 varies by country. In many jurisdictions, it is classified as a controlled substance due to its structural similarity to other synthetic cannabinoids that have been associated with adverse health effects. Researchers must obtain appropriate licenses to study this compound legally.

Potential Applications

While JWH-315 is primarily used in research settings, its selective action on the CB₂ receptor suggests potential applications in the development of new treatments for conditions such as chronic pain, inflammation, and autoimmune diseases. However, further studies are needed to fully understand its pharmacological profile and therapeutic potential.

Safety and Toxicology

As with many synthetic cannabinoids, the safety profile of JWH-315 is not well-established. Potential risks include cardiovascular effects, neurotoxicity, and the possibility of addiction. Researchers must exercise caution and adhere to safety protocols when handling this compound.

Also see

• Synthetic cannabinoids
• Cannabinoid receptor
• JWH-018
• CB1 receptor
• CB2 receptor