JZL 184

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Cat.No. 3836 - JZL 184 | C27H24N2O9 | CAS No. 1101854-58-3
Description: MAGL inhibitor
Chemical Name: 4-[Bis(1,3-benzodioxol-5-yl)hydroxymethyl]-1-piperidinecarboxylic acid 4-nitrophenyl ester
Purity: ≥98% (HPLC)
Datasheet
Citations (4)
Literature

Biological Activity

Potent and selective MAGL inhibitor. Blocks hydrolysis of the endocannabinoid 2-arachidonyl glycerol (2-AG) in vivo in the mouse brain (IC50 = 8 nM). Potentiates depolarization-induced suppression of excitability in cerebellar Purkinje neurons. Exhibits >300-fold selectivity for MAGL over FAAH in vitro. Attenuates nociception in neuropathic and inflammatory pain models. Also reduces free fatty acid levels in primary tumors.

Licensing Information

Sold under license from The Scripps Research Institute.

Compound Libraries

JZL 184 is also offered as part of the Tocriscreen Plus. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 520.49
Formula C27H24N2O9
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 1101854-58-3
PubChem ID 25021165
InChI Key SEGYOKHGGFKMCX-UHFFFAOYSA-N
Smiles O=C(OC6=CC=C([N+]([O-])=O)C=C6)N(CC5)CCC5C(C2=CC=C(OCO3)C3=C2)(O)C1=CC(OCO4)=C4C=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 52.05 100

Preparing Stock Solutions

The following data is based on the product molecular weight 520.49. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.92 mL 9.61 mL 19.21 mL
5 mM 0.38 mL 1.92 mL 3.84 mL
10 mM 0.19 mL 0.96 mL 1.92 mL
50 mM 0.04 mL 0.19 mL 0.38 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Long et al (2009) Selective blockade of 2-arachidonylglycerol hydrolysis produces cannabinoid behavioral effects. Nat.Chem.Biol. 5 37 PMID: 19029917

Pan et al (2009) Blockade of 2-arachidonylglycerol hydrolysis by selective monoacylglycerol lipase inhibitor 4-nitrophenyl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)piperidine-1-carboxylate (JZL184) enhances retrograde endocannabinoid signaling. J.Pharm.Exp.Ther. 331 591 PMID: 19666749

Kinsey et al (2013) Repeated low-dose administration of the monoacylglycerol lipase inhibitor JZL184 retains cannabinoid receptor type 1-mediated antinociceptive and gastroprotective effects. J.Pharmacol.Exp.Ther. 345 492 PMID: 23412396

Zhang et al (2012) Dysregulated lipid metabolism in cancer. World J.Biol.Chem. 3 167 PMID: 22937213


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Keywords: JZL 184, supplier, JZL184, MAGL, inhibitor, MAG, lipase, monoacylglycerol, lipase, inhibitors, inhibits, MGL, MAGL, Tocris Bioscience

4 Citations for JZL 184

Citations are publications that use Tocris products. Selected citations for JZL 184 include:

Valdeolivas et al (2013) The inhibition of 2-arachidonoyl-glycerol (2-AG) biosynthesis, rather than enhancing striatal damage, protects striatal neurons from malonate-induced death: a potential role of cyclooxygenase-2-dependent metabolism of 2-AG. Cell Death Dis 4 e862 PMID: 24136226

Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release. J Biol Chem 288 32685 PMID: 24089517

Martin et al (2015) Endocannabinoids Mediate Muscarinic Acetylcholine Receptor-Dependent Long-Term Depression in the Adult Medial Prefrontal Cortex. Stem Cells Dev 9 457 PMID: 26648844

Sardinha et al (2014) Experimental cannabinoid 2 receptor-mediated immune modulation in sepsis. Front Cell Neurosci 2014 978678 PMID: 24803745


Do you know of a great paper that uses JZL 184 from Tocris? If so please let us know.

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