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JWH-051
Systematic (IUPAC) name
((6aR,10aR)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-9-yl)methanol
Identifiers
CAS number  ?
ATC code  ?
PubChem 9799540
Chemical data
Formula C 25H38O2  
Mol. mass 370.567 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

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.[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. 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
  2. ^ Huffman JW. The search for selective ligands for the CB2 receptor. Current Pharmaceutical Design. 2000 Sep;6(13):1323-37. PMID 10903395
  3. ^ Klein TW, Newton C, Friedman H. Cannabinoid receptors and the cytokine network. Advances in Experimental Medicine and Biology. 1998;437:215-22. PMID 9666274
  4. ^ 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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