JWH-372

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

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| IUPAC_name = naphthalen-1-yl-[1-pentyl-5-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methanone

| image = JWH-372.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 = 914458-28-9

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

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

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| PubChem = 44418325

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

| ChemSpiderID = 23277903

| C=27 | H=24 | F=3 | N=1 | O=1

| smiles = CCCCCN1C=C(C=C1C2=CC=CC=C2C(F)(F)F)C(=O)C3=CC=CC4=CC=CC=C43

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

| StdInChI = 1S/C27H24F3NO/c1-2-3-8-16-31-18-20(17-25(31)23-13-6-7-15-24(23)27(28,29)30)26(32)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3

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

| StdInChIKey = CYPUIQJYGVOHMM-UHFFFAOYSA-N

}}

JWH-372 (naphthalen-1-yl-[1-pentyl-5-[2-(trifluoromethyl)phenyl]pyrrol-3-yl]methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as a potent and selective agonist of the CB₂ receptor.

JWH-372 binds approximately 9 times stronger to the CB₂ receptor (K_i = 8.2 ± 0.2nM) than the CB₁ receptor (K_i = 77 ± 2nM). The selectivity of JWH-372 for the CB₂ receptor is likely due to the electron-withdrawing character of the trifluoromethyl group rather than steric effects, as the o-methyl compound JWH-370 was only mildly selective for the CB₂ receptor (CB₁ K_i = 5.6 ± 0.4nM, CB₂ K_i = 4.0 ± 0.5nM). {{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 }}