JWH-249

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477496189

| IUPAC_name = 2-(2-Bromophenyl)-1-(1-pentylindol-3-yl)ethanone

| image = JWH-249.svg

| width = 150

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = PSA

| legal_US = Schedule I

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 864445-60-3

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

| UNII = H988KQV4U9

| ATC_prefix =

| ATC_suffix =

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

| ChEMBL = 363471

| PubChem = 44397335

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

| DrugBank =

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

| ChemSpiderID = 23253217

| C=21 | H=22 | Br=1 | N=1 | O=1

| smiles = CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3Br

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

| StdInChI = 1S/C21H22BrNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3

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

| StdInChIKey = CGQRVOHECAULLB-UHFFFAOYSA-N

}}

JWH-249 (1-pentyl-3-(2-bromophenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 2.4 times selectivity for CB₁ with a K_i of 8.4 ± 1.8 nM and 20 ± 2 nM at CB₂. Similar to the related 2'-methoxy compound JWH-250, the 2'-chloro compound JWH-203, and the 2'-methyl compound JWH-251, JWH-249 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.{{cite journal | vauthors = Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR | display-authors = 6 | title = 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles | journal = Bioorganic & Medicinal Chemistry Letters | volume = 15 | issue = 18 | pages = 4110–3 | date = September 2005 | pmid = 16005223 | doi = 10.1016/j.bmcl.2005.06.008 }}{{cite journal | vauthors = Manera C, Tuccinardi T, Martinelli A | title = Indoles and related compounds as cannabinoid ligands | journal = Mini Reviews in Medicinal Chemistry | volume = 8 | issue = 4 | pages = 370–87 | date = April 2008 | pmid = 18473928 | doi = 10.2174/138955708783955935 }}

In the United States, CB₁ receptor agonists of the 3-phenylacetylindole class such as cannabipiperidiethanone are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}