JWH-364

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| verifiedrevid =

| IUPAC_name = [5-(4-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl](1-naphthyl)methanone

| image = JWH-364.svg

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| legal_AU =

| legal_CA = Schedule II

| legal_DE =

| legal_UK = Class B

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| CAS_number_Ref = {{cascite|correct}}

| CAS_number = 914458-36-9

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

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| ChEMBL_Ref = {{ebicite|correct|EBI}}

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| PubChem = 44418348

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 23277926

| C=28 | H=29 | N=1 | O=1

| smiles = CCCCCN1C=C(C=C1C2=CC=C(C=C2)CC)C(=O)C3=CC=CC4=CC=CC=C43

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C28H29NO/c1-3-5-8-18-29-20-24(19-27(29)23-16-14-21(4-2)15-17-23)28(30)26-13-9-11-22-10-6-7-12-25(22)26/h6-7,9-17,19-20H,3-5,8,18H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = VJWBAPGRMUZBEH-UHFFFAOYSA-N

}}

JWH-364 ([5-(4-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl](1-naphthyl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 34 ± 3nM) and CB₂ (K_i = 29 ± 1nM) receptors, with a slight selectivity for the latter. JWH-364 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB₁ receptor.{{cite journal | vauthors = Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR | title = 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 16 | issue = 20 | pages = 5432–5 | date = October 2006 | pmid = 16889960 | doi = 10.1016/j.bmcl.2006.07.051 }}