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	370.577 g·mol−1
3D model (JSmol)	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 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

Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, et al. (September 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.
Huffman JW (September 2000). "The search for selective ligands for the CB2 receptor". Current Pharmaceutical Design. 6 (13): 1323–37. doi:10.2174/1381612003399347. PMID 10903395.
Klein TW, Newton C, Friedman H (1998). "Cannabinoid receptors and the cytokine network". Drugs of Abuse, Immunomodulation, and Aids. Advances in Experimental Medicine and Biology. 437. pp. 215–22. doi:10.1007/978-1-4615-5347-2_24. ISBN 978-0-306-45838-5. PMID 9666274.
Griffin G, Fernando SR, Ross RA, McKay NG, Ashford ML, Shire D, et al. (November 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.

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[1] Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, et al. (September 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 (September 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". Drugs of Abuse, Immunomodulation, and Aids. Advances in Experimental Medicine and Biology. 437. pp. 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, et al. (November 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.