JWH-145

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| verifiedrevid =

| IUPAC_name = 1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone

| image = JWH-145.svg

| width =

| tradename =

| pregnancy_AU =

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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 = 914458-19-8

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = JRT5F2Y0NA

| ATC_prefix =

| ATC_suffix =

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

| PubChem = 44418304

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

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

| ChemSpiderID = 23277878

| ChEMBL = 385940

| C=26 | H=25 | N=1 | O=1

| smiles = O=C(C1=CN(CCCCC)C(C2=CC=CC=C2)=C1)C3=C(C=CC=C4)C4=CC=C3

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

| StdInChI = 1S/C26H25NO/c1-2-3-9-17-27-19-22(18-25(27)21-12-5-4-6-13-21)26(28)24-16-10-14-20-11-7-8-15-23(20)24/h4-8,10-16,18-19H,2-3,9,17H2,1H3

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

| StdInChIKey = JLXYYSHMURZHKI-UHFFFAOYSA-N

}}

JWH-145 (1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 14 ± 2nM) and CB₂ (K_i = 6.4 ± 0.4nM) receptors, with a moderate (~2.2x) selectivity for the CB₂ receptor. JWH-145 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 }}