JWH-049

JWH-049 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 psychoactive properties. JWH-049 was developed in the 1990s by John W. Huffman and his team at Clemson University as part of research into the structure-activity relationships of cannabinoids.

Chemical Structure and Properties

JWH-049 is chemically classified as a naphthoylindole, with the systematic name (1-pentyl-1H-indol-3-yl)-1-naphthalenylmethanone. Its molecular formula is C₂₅H₂₃NO, and it has a molecular weight of 353.46 g/mol.

The structure of JWH-049 consists of a naphthalene group attached to a methanone bridge, which is further connected to an indole group with a pentyl chain at the nitrogen atom. This structure is similar to other synthetic cannabinoids, such as JWH-018 and JWH-073, which also feature the naphthoylindole core.

Pharmacology

JWH-049 acts as a full agonist at the CB₁ and CB₂ cannabinoid receptors. These receptors are part of the endocannabinoid system, which plays a role in regulating various physiological processes, including mood, appetite, and pain sensation.

The binding affinity of JWH-049 for the CB₁ receptor is high, with a K_i value in the low nanomolar range, indicating potent activity. This high affinity contributes to its psychoactive effects, which can mimic those of THC, the primary active component of cannabis.

Legal Status

The legal status of JWH-049 varies by country. In many jurisdictions, it is classified as a controlled substance due to its potential for abuse and lack of accepted medical use. In the United States, synthetic cannabinoids like JWH-049 are often listed under the Controlled Substances Act as Schedule I substances.

Potential Risks and Side Effects

The use of JWH-049, like other synthetic cannabinoids, can pose significant health risks. Adverse effects may include tachycardia, hypertension, anxiety, paranoia, and hallucinations. In some cases, severe toxicity can occur, leading to seizures or psychosis.

Research and Applications

While JWH-049 itself is not used in clinical practice, research into synthetic cannabinoids has provided valuable insights into the endocannabinoid system and potential therapeutic targets. Studies continue to explore the role of cannabinoid receptors in various diseases and the development of selective agonists or antagonists for therapeutic use.

Also see

• Synthetic cannabinoids
• JWH-018
• Cannabinoid receptor
• Endocannabinoid system
• John W. Huffman