JWH-149

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (4-Methyl-1-naphthalenyl)(2-methyl-1-pentyl-1H-indol-3-yl)methanone

| image = JWH-149.png

| width = 150

| tradename =

| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = Class B

| legal_US = Schedule I

| legal_status =

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 548461-82-1

| PubChem = 45267820

| ChemSpiderID = 24627235

| UNII = AWD731Y25Z

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

| C=26 | H=27 | N=1 | O=1

| smiles = c4cccc1c4c(ccc1C)C(=O)c3c2ccccc2n(c3C)CCCCC

| StdInChI = 1S/C26H27NO/c1-4-5-10-17-27-19(3)25(23-13-8-9-14-24(23)27)26(28)22-16-15-18(2)20-11-6-7-12-21(20)22/h6-9,11-16H,4-5,10,17H2,1-3H3

| StdInChIKey = JTJAMXUOXJGSCW-UHFFFAOYSA-N

}}

JWH-149 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-pentyl analog of JWH-148. It is a potent but only moderately selective ligand for the CB₂ receptor, with a binding affinity of K_i = 0.73 ± 0.03 nM at this subtype, and more than six times selectivity over the CB₁ subtype.{{cite journal | vauthors = Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Thompson AL, Bushell S, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR | display-authors = 6 | title = Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists | journal = Bioorganic & Medicinal Chemistry | volume = 13 | issue = 1 | pages = 89–112 | date = January 2005 | pmid = 15582455 | doi = 10.1016/j.bmc.2004.09.050 }}

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-149 are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}