JWH-051

Drugbox
IUPAC_name = ((6aR,10aR)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo [c] chromen-9-yl)methanol

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PubChem= 9799540
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C=25 | H=38 | O=2
molecular_weight = 370.567 g/mol
smiles = CCCCCCC(C)(C)c3cc2OC(C)(C)C1CC=C(CO)CC1c2cc3
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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.

JWH-051 retains high affinity for the CB₁ receptor, but is a much stronger agonist for CB₂, with a Ki value of 0.03nM at CB₂ vs 1.20nM at CB₁. [Huffman JW, Yu S, Showalter V, Abood ME, Wiley JL, Compton DR, Martin BR, Bramblett RD, Reggio PH. Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor. "Journal of Medicinal Chemistry" 1996 Sep 27;39(20):3875-7. PMID 8831752] 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. [Huffman JW. The search for selective ligands for the CB2 receptor. "Current Pharmaceutical Design". 2000 Sep;6(13):1323-37. PMID 10903395] [Klein TW, Newton C, Friedman H. Cannabinoid receptors and the cytokine network. "Advances in Experimental Medicine and Biology". 1998;437:215-22. PMID 9666274] [Griffin G, Fernando SR, Ross RA, McKay NG, Ashford ML, Shire D, Huffman JW, Yu S, Lainton JA, Pertwee RG. Evidence for the presence of CB2-like cannabinoid receptors on peripheral nerve terminals. "European Journal of Pharmacology". 1997 Nov 19;339(1):53-61. PMID 9450616]

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