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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.
See also
References
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^ 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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