JWH-164
{{Short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443832018
| IUPAC_name = 7-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
| image = JWH-164.svg
| width = 150
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| legal_US = Schedule I
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 824961-61-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L3432L6CJJ
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| PubChem = 45271217
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID = 24618407
| C=25 | H=25 | N=1 | O=2
| smiles = CCCCCn(c4)c1ccccc1c4C(=O)c2cccc(cc3)c2cc3OC
| StdInChI = 1S/C25H25NO2/c1-3-4-7-15-26-17-23(20-10-5-6-12-24(20)26)25(27)21-11-8-9-18-13-14-19(28-2)16-22(18)21/h5-6,8-14,16-17H,3-4,7,15H2,1-2H3
| StdInChIKey = IJNSZBAEVYRFCH-UHFFFAOYSA-N
}}
JWH-164 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It has approximately equal affinity for the CB1 and CB2 receptors, with a Ki of 6.6 nM at CB1 and 6.9 nM at CB2. JWH-164 is a positional isomer of the related compound JWH-081, but with a methoxy group at the 7-position of the naphthyl ring, rather than the 4-position as in JWH-081. Its potency is intermediate between that of JWH-081 and its ring unsubstituted derivative JWH-018, demonstrating that substitution of the naphthyl 7-position can also result in increased cannabinoid receptor binding affinity.{{cite journal | vauthors = Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Thompson AL, Bushell S, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR | display-authors = 6 | title = Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists | journal = Bioorganic & Medicinal Chemistry | volume = 13 | issue = 1 | pages = 89–112 | date = January 2005 | pmid = 15582455 | doi = 10.1016/j.bmc.2004.09.050 }}{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | year = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }}
In the United States, all CB1 all receptor agonists of the 3-(1-naphthoyl)indole class, including JWH-164, are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}