JWH-015

JWH-015

Systematic (IUPAC) name
(2-Methyl-1-propyl-1H-indol-3-yl)-1-naphthalenylmethanone
Clinical data
Legal status	DE: Anlage II (Prohibited)
Identifiers
CAS Number	155471-08-2 Y
PubChem	CID: 4273754
IUPHAR/BPS	5558
ChemSpider	3480676
Chemical data
Formula	C23H21NO
Molecular mass	327.43 g/mol
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 Key:LJSBBBWQTLXQEN-UHFFFAOYSA-N
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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 28x more strongly to CB₂ than 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 Dr. John W. Huffman.

Metabolism

JWH-015 has been shown in vitro to be metabolised 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

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