JWH-051

JWH-051

Identifiers
IUPAC name ((6aR,10aR)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-9-yl)methanol
PubChem (CID)	9799540
ChemSpider	7975305
Chemical and physical data
Formula	C25H38O2
Molar mass	370.567 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCCCC(C)(C)C1=CC2=C(C=C1)[C@@H]3CC(=CC[C@H]3C(O2)(C)C)CO
InChI InChI=1S/C25H38O2/c1-6-7-8-9-14-24(2,3)19-11-12-20-21-15-18(17-26)10-13-22(21)25(4,5)27-23(20)16-19/h10-12,16,21-22,26H,6-9,13-15,17H2,1-5H3/t21-,22+/m0/s1 Key:ORTVDISIJXKUAV-FCHUYYIVSA-N
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JWH-051 is an analgesic drug which is a cannabinoid agonist. Its chemical structure is closely related to that of the potent cannabinoid agonist HU-210, with the only difference being the removal of the hydroxyl group at position 1 of the aromatic ring. It was discovered and named after Dr. John W. Huffman.

JWH-051 retains high affinity for the CB₁ receptor, but is a much stronger agonist for CB₂, with a Ki value of 14nM at CB₂ vs 19nM at CB₁.^[1] It was one of the first CB₂-selective ligands developed, although its selectivity for CB₂ is modest compared to newer compounds such as HU-308.

It has similar effects to other cannabinoid agonists such as sedation and analgesia, but with a relatively strong antiinflammatory effect due to its strong activity at CB₂.^[2][3][4]

References

1. Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, Martin BR, Bramblett RD, Reggio PH (1996). "Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor". Journal of Medicinal Chemistry. 39 (20): 3875–7. doi:10.1021/jm960394y. PMID 8831752.
2. Huffman JW (2000). "The search for selective ligands for the CB2 receptor". Current pharmaceutical design. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.
3. Klein TW, Newton C, Friedman H (1998). "Cannabinoid receptors and the cytokine network". Advances in experimental medicine and biology. Advances in Experimental Medicine and Biology. 437: 215–22. doi:10.1007/978-1-4615-5347-2_24. ISBN 978-0-306-45838-5. PMID 9666274.
4. Griffin G, Fernando SR, Ross RA, McKay NG, Ashford ML, Shire D, Huffman JW, Yu S, et al. (1997). "Evidence for the presence of CB2-like cannabinoid receptors on peripheral nerve terminals". European Journal of Pharmacology. 339 (1): 53–61. doi:10.1016/S0014-2999(97)01336-8. PMID 9450616.