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JWH-051

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-051
Legal status
Legal status
Identifiers
  • ((6aR,10aR)-6,6-Dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-9-yl)methanol
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC25H38O2
Molar mass370.577 g·mol−1
3D model (JSmol)
  • CCCCCCC(C)(C)C1=CC2=C(C=C1)[C@@H]3CC(=CC[C@H]3C(O2)(C)C)CO
  • 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 ☒N
  • Key:ORTVDISIJXKUAV-FCHUYYIVSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-051 is ananalgesic drug which is acannabinoidagonist. Its chemical structure is closely related to that of the potent cannabinoid agonistHU-210, with the only difference being the removal of the hydroxyl group at position 1 of the aromatic ring. It was discovered and named afterJohn W. Huffman.

JWH-051 retains high affinity for theCB1receptor, but is a much stronger agonist forCB2, with aKi value of 14nM at CB2 vs 19nM at CB1.[2] It was one of the first CB2-selective ligands developed, although its selectivity for CB2 is modest compared to newer compounds such asHU-308.

It has similar effects to other cannabinoid agonists such assedation andanalgesia, but with a relatively strongantiinflammatory effect due to its strong activity at CB2.[3][4][5]

References

[edit]
  1. ^"Stoffe gem. Anlagen zum BtMG". Retrieved2024-11-23.
  2. ^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.
  3. ^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.
  4. ^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. Vol. 437. Boston, MA: Springer. pp. 215–22.doi:10.1007/978-1-4615-5347-2_24.ISBN 978-0-306-45838-5.PMID 9666274.
  5. ^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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