JWH-198

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 451606850

| IUPAC_name = (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone

| image = JWH-198.svg

| width = 150

| 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 =

| routes_of_administration =

| bioavailability =

| protein_bound =

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| elimination_half-life =

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

| CAS_number = 166599-76-4

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

| UNII = J53IGM38PB

| ATC_prefix =

| ATC_suffix =

| PubChem = 10319620

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

| DrugBank =

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

| ChemSpiderID = 8495084

| C=26 | H=26 | N=2 | O=3

| smiles = C4COCCN4CCn2cc(c5ccccc25)C(=O)c3c1ccccc1c(OC)cc3

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

| StdInChI = 1S/C26H26N2O3/c1-30-25-11-10-22(19-6-2-3-8-21(19)25)26(29)23-18-28(24-9-5-4-7-20(23)24)13-12-27-14-16-31-17-15-27/h2-11,18H,12-17H2,1H3

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

| StdInChIKey = QWHSUXWDDKWTOG-UHFFFAOYSA-N

}}

JWH-198 is a drug from the aminoalkylindole and naphthoylindole families which acts as a cannabinoid receptor agonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a binding affinity at the CB₁ receptor of 10 nM, binding around four times more tightly than the parent compound JWH-200, which has no substitution on the naphthoyl ring.{{cite journal | vauthors = Huffman JW, Padgett LW | title = Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes | journal = Current Medicinal Chemistry | volume = 12 | issue = 12 | pages = 1395–411 | year = 2005 | pmid = 15974991 | doi = 10.2174/0929867054020864 }} It has been used mainly in molecular modelling of the cannabinoid receptors.{{cite journal | vauthors = Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, Gruett MD, Kumar V, Estep KG, Olefirowicz EM | title = Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 16 | pages = 3094–105 | date = Aug 1995 | pmid = 7636873 | doi = 10.1021/jm00016a013 }}{{cite journal | vauthors = Shim JY, Collantes ER, Welsh WJ, Subramaniam B, Howlett AC, Eissenstat MA, Ward SJ | title = Three-dimensional quantitative structure-activity relationship study of the cannabimimetic (aminoalkyl)indoles using comparative molecular field analysis | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 23 | pages = 4521–32 | date = Nov 1998 | pmid = 9804691 | doi = 10.1021/jm980305c }}

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-198 are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}