JWH-365

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

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| IUPAC_name = (5-(2-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone

| image = JWH-365.svg

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| legal_CA = Schedule II

| legal_DE =

| legal_UK = Class B

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| CAS_number_Ref = {{cascite|correct}}

| CAS_number = 914458-23-4

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

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

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| PubChem = 44418313

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

| ChemSpiderID = 23277890

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

| smiles = CCCCCN1C=C(C=C1C2=CC=CC=C2CC)C(=O)C3=CC=CC4=CC=CC=C43

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

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

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

| StdInChIKey = SNWJCZXZSGPAJM-UHFFFAOYSA-N

}}

JWH-365 ((5-(2-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 17 ± 1nM) and CB₂ (K_i = 3.4 ± 0.2nM) receptors, with a strong (~5x) selectivity for the CB₂ receptor over the CB₁ receptor. JWH-365 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 }}