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JZL 184

CAS No.:
1101854-58-3
Catalog Number:
AG008SS0
Molecular Formula:
C27H24N2O9
Molecular Weight:
520.4875
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥97%
1 week
United States
$105
- +
10mg
≥97%
1 week
United States
$140
- +
50mg
≥97%
1 week
United States
$397
- +
100mg
≥97%
1 week
United States
$689
- +
Product Description
Catalog Number:
AG008SS0
Chemical Name:
JZL 184
CAS Number:
1101854-58-3
Molecular Formula:
C27H24N2O9
Molecular Weight:
520.4875
MDL Number:
MFCD11976911
IUPAC Name:
(4-nitrophenyl) 4-[bis(1,3-benzodioxol-5-yl)-hydroxymethyl]piperidine-1-carboxylate
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
InChI Key:
SEGYOKHGGFKMCX-UHFFFAOYSA-N
SMILES:
O=C(N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O)Oc1ccc(cc1)[N+](=O)[O-]
UNII:
7MZ1I2J68A
Properties
Complexity:
820  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
520.148g/mol
Formal Charge:
0
Heavy Atom Count:
38  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
520.494g/mol
Monoisotopic Mass:
520.148g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
133A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.2  
Literature
Title Journal
Actions of the dual FAAH/MAGL inhibitor JZL195 in a murine neuropathic pain model. British journal of pharmacology 20160101
Endogenous 2-Arachidonoylglycerol Alleviates Cyclooxygenases-2 Elevation-Mediated Neuronal Injury From SO2 Inhalation via PPARγ Pathway. Toxicological sciences : an official journal of the Society of Toxicology 20151001
Full Fatty Acid Amide Hydrolase Inhibition Combined with Partial Monoacylglycerol Lipase Inhibition: Augmented and Sustained Antinociceptive Effects with Reduced Cannabimimetic Side Effects in Mice. The Journal of pharmacology and experimental therapeutics 20150801
The effect of FAAH, MAGL, and Dual FAAH/MAGL inhibition on inflammatory and colorectal distension-induced visceral pain models in Rodents. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20150701
Endocannabinoids modulate cortical development by configuring Slit2/Robo1 signalling. Nature communications 20140101
Identification of potent Yes1 kinase inhibitors using a library screening approach. Bioorganic & medicinal chemistry letters 20130801
Covalent inhibition of recombinant human carboxylesterase 1 and 2 and monoacylglycerol lipase by the carbamates JZL184 and URB597. Biochemical pharmacology 20121101
Development and characterization of endocannabinoid hydrolases FAAH and MAGL inhibitors bearing a benzotriazol-1-yl carboxamide scaffold. Bioorganic & medicinal chemistry 20121101
Brain phospholipase C, diacylglycerol lipase and monoacylglycerol lipase are involved in (±)-epibatidine-induced activation of central adrenomedullary outflow in rats. European journal of pharmacology 20120915
The temporal dynamics of the effects of monoacylglycerol lipase blockade on locomotion, anxiety, and body temperature. Behavioural pharmacology 20120801
Assay and inhibition of diacylglycerol lipase activity. Bioorganic & medicinal chemistry letters 20120715
Estradiol acutely suppresses inhibition in the hippocampus through a sex-specific endocannabinoid and mGluR-dependent mechanism. Neuron 20120607
Highly selective inhibitors of monoacylglycerol lipase bearing a reactive group that is bioisosteric with endocannabinoid substrates. Chemistry & biology 20120525
Characterization of the effects of reuptake and hydrolysis inhibition on interstitial endocannabinoid levels in the brain: an in vivo microdialysis study. ACS chemical neuroscience 20120516
Gating the polarity of endocannabinoid-mediated synaptic plasticity by nitric oxide in the spinal locomotor network. The Journal of neuroscience : the official journal of the Society for Neuroscience 20120411
Inhibition of monoacylglycerol lipase attenuates vomiting in Suncus murinus and 2-arachidonoyl glycerol attenuates nausea in rats. British journal of pharmacology 20120401
Cannabinoids mediate opposing effects on inflammation-induced intestinal permeability. British journal of pharmacology 20120401
Dual inhibition of MAGL and type II topoisomerase by N-phenylmaleimides as a potential strategy to reduce neuroblastoma cell growth. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20120214
Structure-activity relationship of a new series of reversible dual monoacylglycerol lipase/fatty acid amide hydrolase inhibitors. Journal of medicinal chemistry 20120126
Reversible gating of endocannabinoid plasticity in the amygdala by chronic stress: a potential role for monoacylglycerol lipase inhibition in the prevention of stress-induced behavioral adaptation. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20111201
The design, synthesis and biological evaluation of novel URB602 analogues as potential monoacylglycerol lipase inhibitors. Bioorganic & medicinal chemistry letters 20111115
Endocannabinoid hydrolysis generates brain prostaglandins that promote neuroinflammation. Science (New York, N.Y.) 20111111
Blockade of endocannabinoid hydrolytic enzymes attenuates precipitated opioid withdrawal symptoms in mice. The Journal of pharmacology and experimental therapeutics 20111001
Enhancement of endocannabinoid signaling with JZL184, an inhibitor of the 2-arachidonoylglycerol hydrolyzing enzyme monoacylglycerol lipase, produces anxiolytic effects under conditions of high environmental aversiveness in rats. Pharmacological research 20110901
Inhibition of monoacylglycerol lipase attenuates nonsteroidal anti-inflammatory drug-induced gastric hemorrhages in mice. The Journal of pharmacology and experimental therapeutics 20110901
Differential role of anandamide and 2-arachidonoylglycerol in memory and anxiety-like responses. Biological psychiatry 20110901
Peripheral antinociceptive effects of inhibitors of monoacylglycerol lipase in a rat model of inflammatory pain. British journal of pharmacology 20110801
Inhibition of COX-2 expression by endocannabinoid 2-arachidonoylglycerol is mediated via PPAR-γ. British journal of pharmacology 20110801
Increasing endogenous 2-arachidonoylglycerol levels counteracts colitis and related systemic inflammation. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20110801
Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain. Pharmacological research 20110701
Effect of developmental chlorpyrifos exposure, on endocannabinoid metabolizing enzymes, in the brain of juvenile rats. Toxicological sciences : an official journal of the Society of Toxicology 20110701
Endogenously generated 2-arachidonoylglycerol plays an inhibitory role in bombesin-induced activation of central adrenomedullary outflow in rats. European journal of pharmacology 20110511
Endocannabinoid 2-arachidonoylglycerol protects neurons against β-amyloid insults. Neuroscience 20110331
Inhibition of endocannabinoid catabolic enzymes elicits anxiolytic-like effects in the marble burying assay. Pharmacology, biochemistry, and behavior 20110301
Inactivation of lipid glyceryl ester metabolism in human THP1 monocytes/macrophages by activated organophosphorus insecticides: role of carboxylesterases 1 and 2. Chemical research in toxicology 20101220
Inhibition of monoacylglycerol lipase by troglitazone, N-arachidonoyl dopamine and the irreversible inhibitor JZL184: comparison of two different assays. British journal of pharmacology 20101201
Inhibitors of monoacylglycerol lipase, fatty-acid amide hydrolase and endocannabinoid transport differentially suppress capsaicin-induced behavioral sensitization through peripheral endocannabinoid mechanisms. Pharmacological research 20100901
Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system. Nature neuroscience 20100901
High-performance liquid chromatography assay with fluorescence detection for the evaluation of inhibitors against human recombinant monoacylglycerol lipase. Analytical biochemistry 20100415
Synthesis and evaluation of paracetamol esters as novel fatty acid amide hydrolase inhibitors. Journal of medicinal chemistry 20100311
Characterization of tunable piperidine and piperazine carbamates as inhibitors of endocannabinoid hydrolases. Journal of medicinal chemistry 20100225
Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors. Journal of medicinal chemistry 20091210
Monoacylglycerol lipase limits the duration of endocannabinoid-mediated depolarization-induced suppression of excitation in autaptic hippocampal neurons. Molecular pharmacology 20091201
Dual blockade of FAAH and MAGL identifies behavioral processes regulated by endocannabinoid crosstalk in vivo. Proceedings of the National Academy of Sciences of the United States of America 20091201
Blockade of 2-arachidonoylglycerol 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. The Journal of pharmacology and experimental therapeutics 20091101
Blockade of endocannabinoid-degrading enzymes attenuates neuropathic pain. The Journal of pharmacology and experimental therapeutics 20090901
Characterization of monoacylglycerol lipase inhibition reveals differences in central and peripheral endocannabinoid metabolism. Chemistry & biology 20090731
Inhibitors of endocannabinoid-metabolizing enzymes reduce precipitated withdrawal responses in THC-dependent mice. The AAPS journal 20090601
Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nature chemical biology 20090101
Properties