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Submit ReviewJZL 184
Description: Potent MAGL inhibitor
Chemical Name: 4-[Bis(1,3-benzodioxol-5-yl)hydroxymethyl]-1-piperidinecarboxylic acid 4-nitrophenyl ester
Purity: ≥98% (HPLC)
Biological Activity for JZL 184
JZL 184 is a 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 for JZL 184
JZL 184 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for JZL 184
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for JZL 184
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 52.05 | 100 |
Preparing Stock Solutions for JZL 184
The following data is based on the product molecular weight 520.49. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| 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 for JZL 184
References for JZL 184
References are publications that support the biological activity of the product.
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
If you know of a relevant reference for JZL 184, please let us know.
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Keywords: JZL 184, JZL 184 supplier, JZL184, MAGL, inhibitor, MAG, lipase, monoacylglycerol, inhibitors, inhibits, MGL, 3836, Tocris Bioscience
12 Citations for JZL 184
Citations are publications that use Tocris products. Selected citations for JZL 184 include:
Iryna M et al (2021) Increased 2-arachidonoyl-sn-glycerol levels normalize cortical responses to sound and improve behaviors in Fmr1 KO mice. J Neurodev Disord 13 47 PMID: 34645383
Gary et al (2021) Rapid Aging in the Perforant Path Projections to the Rodent Dentate Gyrus. J Neurosci 41 2301-2312 PMID: 33514675
Argueta et al (2019) Cannabinoid CB1 Receptors Inhibit Gut-Brain Satiation Signaling in Diet-Induced Obesity. Front Physiol 10 704 PMID: 31281260
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 Ins release. J Biol Chem 288 32685 PMID: 24089517
Hu et al (2019) Endocannabinoid Signaling Mediates Local Dendritic Coordination between Excitatory and Inhibitory Synapses. Cell Rep 27 666 PMID: 30995465
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
Praveen et al (2022) The Endocannabinoid Analgesic Entourage Effect: Investigations in Cultured DRG Neurons. J Pain Res 15 3493-3507 PMID: 36394060
Giulio G et al (2022) Identification of an endocannabinoid gut-brain vagal mechanism controlling food reward and energy homeostasis. Mol Psychiatry 27 2340-2354 PMID: 35075269
Bashashati et al (2015) Inhibiting endocannabinoid biosynthesis: a novel approach to the treatment of constipation. Br J Pharmacol 172 3099 PMID: 25684407
Miriam et al (2020) 2-arachidonoylglycerol reduces chondroitin sulphate proteoglycan production by astrocytes and enhances oligodendrocyte differentiation under inhibitory conditions. Glia 68 1255-1273 PMID: 31894889
Do you know of a great paper that uses JZL 184 from Tocris? Please let us know.
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