:JWH-185

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 3-[(4-Methoxy-1-naphthalenyl)methyl]-1-pentyl-1H-indole

| image = JWH-185.png

| image_class = skin-invert-image

| width = 180

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| legal_UK = Class B

| legal_US = Schedule I

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| CAS_number = 619294-39-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T981O5QY3V

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| ChemSpiderID = 35303440

| C=25 | H=27 | N=1 | O=1

| smiles = CCCCCn1cc(c2c1cccc2)Cc3ccc(c4c3cccc4)OC

| StdInChI = 1S/C25H27NO/c1-3-4-9-16-26-18-20(22-11-7-8-13-24(22)26)17-19-14-15-25(27-2)23-12-6-5-10-21(19)23/h5-8,10-15,18H,3-4,9,16-17H2,1-2H3

| StdInChIKey = OTYBPWBZUDBUQS-UHFFFAOYSA-N

}}

JWH-185 is a synthetic cannabinoid receptor ligand from the naphthoylindole family. It is the carbonyl-reduced derivative of related compound JWH-081. The binding affinity of JWH-185 for the CB₁ receptor is reported as K_i = 17 ± 3 nM.{{cite journal |vauthors=Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR | title = 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor | journal = Bioorg. Med. Chem. | volume = 11 | issue = 4 | pages = 539–549 | year = 2003 | pmid = 12538019| doi = 10.1016/s0968-0896(02)00451-0| s2cid = 29107765 }}

In the United States, all CB₁ receptor agonists of the 3-(1-naphthylmethane)indole class such as JWH-185 are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}