JWH-015

JWH-015

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I
Identifiers
IUPAC name (2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone
CAS Number	155471-08-2 Y
PubChem CID	4273754
IUPHAR/BPS	5558
ChemSpider	3480676 N
UNII	W4FL204T10
CompTox Dashboard (EPA)	DTXSID60165902
ECHA InfoCard	100.161.912
Chemical and physical data
Formula	C23H21NO
Molar mass	327.427 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN1C(=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43)C
InChI InChI=1S/C23H21NO/c1-3-15-24-16(2)22(20-12-6-7-14-21(20)24)23(25)19-13-8-10-17-9-4-5-11-18(17)19/h4-14H,3,15H2,1-2H3 N Key:LJSBBBWQTLXQEN-UHFFFAOYSA-N N
NY (what is this?)  (verify)

JWH-015 is a chemical from the naphthoylindole family that acts as a subtype-selective cannabinoid 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 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 of the naphthalene ring, similar to the metabolic pathways seen for other aminoalkylindole cannabinoids such as WIN 55,212-2.Epoxidation of polycyclic aromatic hydrocarbons (see for example benzo(a)pyrene toxicity) can produce carcinogenic 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 Substances.

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