JWH-398

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 445719689

| IUPAC_name = 1-Pentyl-3-(4-chloro-1-naphthoyl)indole

| image = JWH-398.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = Class B

| legal_US = Schedule I

| legal_status = Illegal in Latvia[http://www.likumi.lv/doc.php?id=201101&from=off Grozījumi Ministru kabineta 2005.gada 8.novembra noteikumos Nr.847 "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem"]

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 1292765-18-4

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

| UNII = RX0E95S90H

| ATC_prefix =

| ATC_suffix =

| PubChem =

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

| DrugBank =

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

| ChemSpiderID = 28647395

| C=24 | H=22 | Cl=1 | N=1 | O=1

| smiles = c14ccccc1n(CCCCC)cc4C(=O)c(cc3)c2ccccc2c3Cl

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

| StdInChI = 1S/C24H22ClNO/c1-2-3-8-15-26-16-21(19-11-6-7-12-23(19)26)24(27)20-13-14-22(25)18-10-5-4-9-17(18)20/h4-7,9-14,16H,2-3,8,15H2,1H3

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

| StdInChIKey = IUWBHGFOHXVVKV-UHFFFAOYSA-N

}}

JWH-398 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors. It has mild selectivity for CB₁ with a K_i of 2.3 nM and 2.8 nM at CB₂.{{cite book | doi = 10.1007/978-1-59745-503-9| series = The Cannabinoid Receptors. The Receptors. | year = 2009| vauthors = Huffman JW | title = Cannabimimetic Indoles, Pyrroles, and Indenes: Structure–Activity Relationships and Receptor Interactions | veditors = Reggio PH | publisher = Humana Press | isbn = 978-1-58829-712-9}} This synthetic chemical compound was identified by the EMCDDA as an ingredient in three separate "herbal incense" products purchased from online shops between February and June 2009.{{cite web | url = http://www.emcdda.europa.eu/attachements.cfm/att_80086_EN_Spice%20Thematic%20paper%20%E2%80%94%20final%20version.pdf | title = Understanding the 'Spice' phenomenon | publisher = EMCDDA | location = Lisbon | date = November 2009 | access-date = 2009-11-05 | archive-date = 2010-04-08 | archive-url = https://web.archive.org/web/20100408172523/http://www.emcdda.europa.eu/attachements.cfm/att_80086_EN_Spice%20Thematic%20paper%20%E2%80%94%20final%20version.pdf | url-status = dead }} It was discovered by, and named after, John W. Huffman.{{cite conference | vauthors = Huffman JW, etal | title = Structure-Activity Relationships at the cb1 and cb2 Receptors for 1-Alkyl-3-(1-Naphthoyl-4 and 8-Halogen Substituted) Indoles | date = 2009 | conference = 19th Annual Symposium on the Cannabinoids | location = Burlington, Vermont | publisher = International Cannabinoid Research Society | page = 2 }}

In the United States, JWH-398 is a Schedule I controlled substance.[https://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf Controlled Substances listed by the DEA]