JWH-116

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (2-Ethyl-1-pentyl-1H-indol-3-yl)-1-naphthalenylmethanone

| image = JWH-116.png

| width = 150

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| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = Class B

| legal_US = Schedule I

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| CAS_number = 619294-64-3

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| UNII = RKP962UAI3

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

| ChemSpiderID = 29341485

| C=26 | H=27 | N=1 | O=1

| smiles = CCCCCN1C2=CC=CC=C2C(=C1CC)C(=O)C3=CC=CC4=CC=CC=C43

| StdInChI = 1S/C26H27NO/c1-3-5-10-18-27-23(4-2)25(22-15-8-9-17-24(22)27)26(28)21-16-11-13-19-12-6-7-14-20(19)21/h6-9,11-17H,3-5,10,18H2,1-2H3

| StdInChIKey = AQHPTHKEKSWGPO-UHFFFAOYSA-N

}}

JWH-116 is a synthetic cannabinoid receptor ligand from the naphthoylindole family. It is the indole 2-ethyl derivative of related compound JWH-018. The binding affinity of JWH-116 for the CB₁ receptor is reported as K_i = 52 ± 5 nM.{{cite journal | vauthors = Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR | display-authors = 6 | title = 3-Indolyl-1-naphthylmethanes: new cannabimimetic indoles provide evidence for aromatic stacking interactions with the CB(1) cannabinoid receptor | journal = Bioorganic & Medicinal Chemistry | volume = 11 | issue = 4 | pages = 539–49 | date = February 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-naphthoyl)indole class such as JWH-116 are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}