JWH-015 is a chemical from the

naphthoylindole Naphthoylindoles are a class of synthetic cannabinoids. See also * Structural scheduling of synthetic cannabinoids References {{reflist ...

family that acts as a subtype-selective

cannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

agonist. Its affinity for CB₂ receptors is 13.8 nM, while its affinity for CB₁ is 383 nM, meaning that it binds almost 28 times more strongly to CB₂ than to CB₁. However, it still displays some CB₁ activity, and in some model systems can be very potent and efficacious at activating CB₁ receptors, and therefore it is not as selective as newer drugs such as JWH-133. It has been shown to possess

immunomodulatory Immunotherapy or biological therapy is the treatment of disease by activating or suppressing the immune system. Immunotherapies designed to elicit or amplify an immune response are classified as ''activation immunotherapies,'' while immunotherap ...

effects, and CB₂ agonists may be useful in the treatment of pain and inflammation. It was discovered and named after John W. Huffman.

Metabolism

JWH-015 has been shown ''in vitro'' to be metabolized primarily by hydroxylation and ''N''- dealkylation, and also by

epoxidation In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale ...

of the naphthalene ring, similar to the metabolic pathways seen for other

aminoalkylindole Aminoalkylindoles (AAIs) are a family of cannabinergic compound that act as a cannabinoid receptor agonist. They were invented by pharmaceutical company Sterling-Winthrop in the early 1990s as potential nonsteroidal anti-inflammatory agents. Leg ...

cannabinoids Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

such as

WIN 55,212-2 WIN 55,212-2 is a chemical described as an aminoalkylindole derivative, which produces effects similar to those of cannabinoids such as tetrahydrocannabinol (THC) but has an entirely different chemical structure. WIN 55,212-2 is a potent canna ...

Epoxidation In organic chemistry, an epoxide is a cyclic ether () with a three-atom ring. This ring approximates an equilateral triangle, which makes it strained, and hence highly reactive, more so than other ethers. They are produced on a large scale ...

polycyclic aromatic hydrocarbon A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. ...

s (see for example benzo(a)pyrene toxicity) can produce

carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subs ...

metabolites, although there is no evidence to show that JWH-015 or other aminoalkylindole cannabinoids are actually carcinogenic ''in vivo''. A study published in the ''British Journal of Cancer'' shows that JWH-015 may signal certain cancers to shrink through a process called apoptosis.

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-015 are

Schedule I Controlled Substance This is the list of Schedule I drugs as defined by the United States Controlled Substances Act. 21 CFRbr>1308.11(CSA Sched I) with changes through (Oct 18, 2012). Retrieved September 6, 2013. The following findings are required for drugs to be pla ...

s. As of October 2015 JWH-015 is a controlled substance in China.

References

{{Cannabinoids Naphthoylindoles JWH cannabinoids Designer drugs CB1 receptor agonists CB2 receptor agonists