JWH-009

Synthetic cannabinoid

CaptionSynonyms

JWH-009

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

JWH-009 is a synthetic cannabinoid that acts as a potent agonist of the cannabinoid receptors. It is part of the naphthoylindole family of synthetic cannabinoids, which were originally developed for research purposes to study the endocannabinoid system.

Chemical Structure and Properties

JWH-009 is chemically classified as a naphthoylindole, which is a subclass of synthetic cannabinoids. Its chemical structure is characterized by a naphthalene ring system linked to an indole moiety. The IUPAC name for JWH-009 is (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol. The molecular formula is C23H34O3, and it has a molecular weight of 358.51 g/mol.

Pharmacology

JWH-009 acts as a full agonist at the CB1 receptor and CB2 receptor, with a higher affinity for the CB1 receptor. This receptor is primarily found in the central nervous system, where it modulates neurotransmitter release, leading to effects such as analgesia, euphoria, and altered perception. The CB2 receptor is mainly found in the immune system, and its activation can lead to anti-inflammatory effects.

Synthesis and Development

JWH-009 was first synthesized by John W. Huffman and his team at Clemson University as part of a series of compounds designed to investigate the structure-activity relationships of cannabinoids. The synthesis involves the condensation of a naphthoyl chloride with an indole derivative, followed by further chemical modifications to introduce the desired functional groups.

Legal Status

Due to its psychoactive properties and potential for abuse, JWH-009, like many other synthetic cannabinoids, has been classified as a controlled substance in many countries. It is often included in legislation targeting "designer drugs" or "novel psychoactive substances" (NPS).

Health Effects and Risks

The use of JWH-009, particularly in unregulated products, poses significant health risks. Adverse effects can include tachycardia, hypertension, anxiety, paranoia, and hallucinations. Long-term use may lead to addiction and psychosis.

Research Applications

Despite its potential for abuse, JWH-009 and similar compounds are valuable tools in scientific research. They are used to study the endocannabinoid system, explore potential therapeutic applications of cannabinoids, and develop new treatments for conditions such as chronic pain, multiple sclerosis, and cancer.

Also see

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