JZL184

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.

JZL184

Names
IUPAC name 4-nitrophenyl-4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
Identifiers
CAS Number	1101854-58-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:95015
ChEMBL	ChEMBL576786
ChemSpider	21467840
PubChem CID	25021165
UNII	7MZ1I2J68A
InChI 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 Key: SEGYOKHGGFKMCX-UHFFFAOYSA-N
SMILES c1cc(ccc1[N+](=O)[O-])OC(=O)N2CCC(CC2)C(c3ccc4c(c3)OCO4)(c5ccc6c(c5)OCO6)O
Properties
Chemical formula	C27H24N2O9
Molar mass	520.15 g/mol
Appearance	Pale yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

See also

• JZL195

References

1. 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.