JWH-051

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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	C25H38O2
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]

[edit] 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

v • d • e Cannabinoids Plant cannabinoids CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV Cannabinoid metabolites 11-Hydroxy-THC • 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA) Synthetic cannabinoid agonists Classical cannabinoids (Dibenzopyrans) A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • O-2694 • Parahexyl • THC-O-acetate • THC-O-phosphate Nonclassical cannabinoids CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene Aminoalkylindoles AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2 Aminoalkylpyrroles JWH-030 • JWH-147 • JWH-307 Eicosanoids AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861 Others BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220 Endocannabinoid activity enhancers AM-404 • N-arachidonoyl-serotonin • O-1624 • URB-597 • URB-754 Cannabinoid antagonists and inverse agonists AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR