JWH-051

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JWH-051
JWH-051.png
Systematic (IUPAC) name
((6aR,10aR)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-9-yl)methanol
Clinical data
Legal status
?
Identifiers
CAS number  YesY
ATC code ?
PubChem CID 9799540
ChemSpider 7975305
Chemical data
Formula C25H38O2 
Mol. mass 370.567 g/mol
 YesY (what is this?)  (verify)

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[edit]

  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 Medical 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.