JWH-250

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 406104785

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

| image = JWH-250.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = S9

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule II

| legal_UK = Class B

| legal_US = Schedule I

| legal_DE = Anlage II{{cite web | title=Stoffe gem. Anlagen zum BtMG | url=https://www.bfarm.de/SharedDocs/Downloads/DE/Bundesopiumstelle/Betaeubungsmittel/BtM-Stoffe.xls?__blob=publicationFile | access-date=2024-11-23}}

| legal_status = Illegal in Czech Republic and Latvia[http://www.likumi.lv/doc.php?id=201101&from=off Legal article in Latvian (www.likumi.lv)]

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 864445-43-2

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

| UNII = IP9911R8A0

| ATC_prefix =

| ATC_suffix =

| PubChem = 44397540

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

| DrugBank =

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 188031

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 23256117

| C=22 | H=25 | N=1 | O=2

| smiles = COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C22H25NO2/c1-3-4-9-14-23-16-19(18-11-6-7-12-20(18)23)21(24)15-17-10-5-8-13-22(17)25-2/h5-8,10-13,16H,3-4,9,14-15H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = FFLSJIQJQKDDCM-UHFFFAOYSA-N

}}

JWH-250 or (1-pentyl-3-(2-methoxyphenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors, with a K_i of 11 nM at CB₁ and 33 nM at CB₂. Unlike many of the older JWH series compounds, this compound does not have a naphthalene ring, instead occupying this position with a 2'-methoxy-phenylacetyl group, making JWH-250 a representative member of a new class of cannabinoid ligands.{{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 }} Other 2'-substituted analogues such as the methyl, chloro and bromo compounds are also active and somewhat more potent.{{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 }}The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. {{ISBN|978-1-58829-712-9}}