JWH-164
Chemical compound
- US: Schedule I
- 7-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
- 824961-61-7
Y
- 45271217
- 24618407
- L3432L6CJJ
- DTXSID70669880
- Interactive image
- CCCCCn(c4)c1ccccc1c4C(=O)c2cccc(cc3)c2cc3OC
InChI
- InChI=1S/C25H25NO2/c1-3-4-7-15-26-17-23(20-10-5-6-12-24(20)26)25(27)21-11-8-9-18-13-14-19(28-2)16-22(18)21/h5-6,8-14,16-17H,3-4,7,15H2,1-2H3
- Key:IJNSZBAEVYRFCH-UHFFFAOYSA-N
JWH-164 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It has approximately equal affinity for the CB1 and CB2 receptors, with a Ki of 6.6 nM at CB1 and 6.9 nM at CB2. JWH-164 is a positional isomer of the related compound JWH-081, but with a methoxy group at the 7-position of the naphthyl ring, rather than the 4-position as in JWH-081. Its potency is intermediate between that of JWH-081 and its ring unsubstituted derivative JWH-018, demonstrating that substitution of the naphthyl 7-position can also result in increased cannabinoid receptor binding affinity.[1][2]
In the United States, all CB1 all receptor agonists of the 3-(1-naphthoyl)indole class, including JWH-164, are Schedule I Controlled Substances.[3]
References
- ^ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "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". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
- ^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
- ^ 21 U.S.C. § 812: Schedules of controlled substances
- v
- t
- e
(comparison)
| Cannabibutols |
|
|---|---|
| Cannabichromenes | |
| Cannabicyclols |
|
| Cannabidiols | |
| Cannabielsoins |
|
| Cannabigerols | |
| Cannabiphorols |
|
| Cannabinols | |
| Cannabitriols |
|
| Cannabivarins |
|
| Delta-8-tetrahydrocannabinols |
|
| Delta-9-tetrahydrocannabinols | |
| Delta-10-Tetrahydrocannabinols | |
| Miscellaneous cannabinoids |
|
| Active metabolites |
- Arachidonoyl ethanolamide (AEA; anandamide)
- 2-Arachidonoylglycerol (2-AG)
- 2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
- 2-Oleoylglycerol (2-OG)
- N-Arachidonoyl dopamine (NADA)
- N-Arachidonylglycine (NAGly)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- N-Arachidonoyl serotonin (AA-5-HT)
- Docosatetraenoylethanolamide (DEA)
- Lysophosphatidylinositol (LPI)
- Oleamide
- Oleoylethanolamide (OEA)
- Palmitoylethanolamide (PEA)
- RVD-Hpα
- Stearoylethanolamide (SEA)
- O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
cannabinoid
receptor
agonists /
neocannabinoids
| Classical cannabinoids (dibenzopyrans) |
|
|---|---|
| Non-classical cannabinoids |
|
| Adamantoylindoles |
|
| Benzimidazoles | |
| Benzoylindoles |
|
| Cyclohexylphenols | |
| Eicosanoids |
|
| Hydrocarbons | |
| Indazole carboxamides | |
| Indazole-3- carboxamides |
|
| Indole-3-carboxamides |
|
| Indole-3-carboxylates | |
| Naphthoylindazoles | |
| Naphthoylindoles |
|
| Naphthoylpyrroles | |
| Naphthylmethylindenes | |
| Naphthylmethylindoles | |
| Phenylacetylindoles | |
| Pyrazolecarboxamides |
|
| Pyrrolobenzoxazines | |
| Quinolinyl esters | |
| Tetramethylcyclo- propanoylindazoles | |
| Tetramethylcyclo- propanoylindoles | |
| Tetramethylcyclo- propylindoles | |
| Others |
|
enhancers
(inactivation inhibitors)
- 4-Nonylphenylboronic acid
- AM-404
- Arachidonoyl serotonin
- Arvanil
- BIA 10-2474
- Biochanin A
- CAY-10401
- CAY-10429
- Genistein
- Guineesine
- IDFP
- JNJ 1661010
- JNJ-42165279
- JZL184
- JZL195
- Kaempferol
- LY-2183240
- MK-4409
- O-1624
- O-2093
- Oleoylethanolamide (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(antagonists/inverse
agonists/antibodies)
- AM-251
- AM-281
- AM-630
- AM-1387
- AM-4113
- AM-6527
- AM-6545
- BML-190
- Brizantin (Бризантин)
- CAY-10508
- CB-25
- CB-52
- CB-86
- Dietressa (Диетресса)
- Drinabant (AVE1625)
- Hemopressin
- Ibipinabant (SLV319)
- JTE-907
- LH-21
- LY-320,135
- MDA-77
- MJ-15
- MK-9470
- NESS-0327
- NIDA-41020
- O-606
- O-1184
- O-1248
- O-1918
- O-2050
- O-2654
- Otenabant (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics
 | This cannabinoid related article is a stub. You can help Wikipedia by expanding it. |
- v
- t
- e
