From Wikipedia, the free encyclopedia
JZL184
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| Names
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Preferred IUPAC name
4-Nitrophenyl 4-[di(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
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| Identifiers
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| ChEBI
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| ChEMBL
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| ChemSpider
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| UNII
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InChI=1S/C27H24N2O9/c30-26(38-21-5-3-20(4-6-21)29(32)33)28-11-9-17(10-12-28)27(31,18-1-7-22-24(13-18)36-15-34-22)19-2-8-23-25(14-19)37-16-35-23/h1-8,13-14,17,31H,9-12,15-16H2 NKey: SEGYOKHGGFKMCX-UHFFFAOYSA-N N
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c1cc(ccc1[N+](=O)[O-])OC(=O)N2CCC(CC2)C(c3ccc4c(c3)OCO4)(c5ccc6c(c5)OCO6)O
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| Properties
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C27H24N2O9
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| Molar mass
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520.15 g/mol
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| Appearance
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Pale yellow solid
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
JZL184 is an irreversible inhibitor for monoacylglycerol lipase (MAGL), the primary enzyme responsible for degrading the endocannabinoid 2-arachidonoylglycerol (2-AG).[1] It displays high selectivity for MAGL over other brain serine hydrolases, including the anandamide-degrading enzyme fatty acid amide hydrolase (FAAH), thereby making it a useful tool for studying the effects of endogenous 2-AG signaling, in vivo. Administration of JZL184 to mice was reported to cause dramatic elevation of brain 2-AG leading to several cannabinoid-related behavioral effects.
- ^ Long JZ, Li W, Booker L, Burston JJ, Kinsey SG, Schlosburg JE, Pavón FJ, Serrano AM, Selley DE, Parsons LH, Lichtman AH, Cravatt BF (November 2008). "Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects". Nat. Chem. Biol. 5 (1): 37–44. doi:10.1038/nchembio.129. PMC 2605181. PMID 19029917.
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Phytocannabinoids (comparison) | | Cannabibutols | |
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| Cannabichromenes | |
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| Cannabicyclols | |
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| Cannabidiols | |
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| Cannabielsoins | |
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| Cannabigerols | |
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| Cannabiphorols | |
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| Cannabinols | |
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| Cannabitriols | |
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| Cannabivarins | |
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| Delta-3-tetrahydrocannabinols | |
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| Delta-4-tetrahydrocannabinols | |
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| Delta-7-tetrahydrocannabinols | |
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| Delta-8-tetrahydrocannabinols | |
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| Delta-9-tetrahydrocannabinols | |
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| Delta-10-Tetrahydrocannabinols | |
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| Delta-11-Tetrahydrocannabinols | |
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| Miscellaneous cannabinoids | |
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| Active metabolites | |
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| Endocannabinoids | |
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Synthetic cannabinoid receptor agonists / neocannabinoids | Classical cannabinoids (dibenzopyrans) | |
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Non-classical cannabinoids | |
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| Adamantoylindoles | |
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| Benzimidazoles | |
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| Benzoylindoles | |
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| Cyclohexylphenols | |
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| Eicosanoids | |
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Indazole-3- carboxamides | |
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| Indole-3-carboxamides | |
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| Indole-3-carboxylates | |
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| Naphthoylindazoles | |
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| Naphthoylindoles | |
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| Naphthoylpyrroles | |
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| Naphthylmethylindenes | |
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| Naphthylmethylindoles | |
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| Phenylacetylindoles | |
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| Pyrazolecarboxamides | |
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Tetramethylcyclo- propanoylindazoles | |
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Tetramethylcyclo- propanoylindoles | |
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| Others | |
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| Allosteric CBRTooltip Cannabinoid receptor ligands | |
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Endocannabinoid enhancers (inactivation inhibitors) | |
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Anticannabinoids (antagonists/inverse agonists/antibodies) | |
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Receptor (ligands) | | CB1Tooltip Cannabinoid receptor type 1 | Agonists (abridged, full list) | |
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| Inverse agonists | |
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| Antagonists | |
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| CB2Tooltip Cannabinoid receptor type 2 | | Agonists |
- 2-AG
- 2-AGE (noladin ether)
- 3,3'-Diindolylmethane
- 4-O-Methylhonokiol
- α-Amyrin · β-Amyrin
- A-796,260
- A-834,735
- A-836,339
- AM-1172
- AM-1221
- AM-1235
- AM-1241
- AM-2232
- Anandamide
- AZ-11713908
- Cannabinol
- Caryophyllene
- CB-13
- CBS-0550
- CP 55,940
- GW-405,833 (L-768,242)
- GW-842,166X
- HU-308
- JTE 7-31
- JWH-007
- JWH-015
- JWH-018
- JWH-73
- JWH-133
- L-759,633
- L-759,656
- Lenabasum (anabasum)
- Magnolol
- MDA-19
- Nabitan
- NADA
- Olorinab (APD-371)
- PF-03550096
- S-444,823
- SER-601
- Serinolamide A
- UR-144
- Tedalinab
- THC (dronabinol)
- THCV
- Tetrahydromagnolol
- Virodhamine
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| Antagonists | |
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NAGly (GPR18) | |
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| GPR55 | |
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| GPR119 | |
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Transporter (modulators) | | eCBTsTooltip Endocannabinoid transporter | |
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Enzyme (modulators) | |
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| Others |
- Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
- ARN-272 (FAAH-like anandamide transporter inhibitor)
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