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MedKoo Cat#: 510320 | Name: JZL184
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

JZL184 is highly selective, and potent MAGL inhibitor ( monoacylglycerol lipase inhibitor). JZL184 improves behavior and neural properties in Ts65Dn mice, a model of down syndrome. JZL184 attenuates LPS-induced increases in cytokine expression in the rat frontal cortex and plasma: differential mechanisms of action. JZL184 also suppresses inflammatory pain in the mouse carrageenan model.

Chemical Structure

JZL184
JZL184
CAS#1101854-58-3

Theoretical Analysis

MedKoo Cat#: 510320

Name: JZL184

CAS#: 1101854-58-3

Chemical Formula: C27H24N2O9

Exact Mass: 520.1482

Molecular Weight: 520.49

Elemental Analysis: C, 62.30; H, 4.65; N, 5.38; O, 27.67

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,350.00 2 Weeks
1g USD 2,050.00 2 Weeks
2g USD 3,450.00 2 Weeks
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Related CAS #
No Data
Synonym
JZL184; JZL 184; JZL-184.
IUPAC/Chemical Name
4-nitrophenyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)piperidine-1-carboxylate.
InChi Key
SEGYOKHGGFKMCX-UHFFFAOYSA-N
InChi Code
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
SMILES Code
O=C(N1CCC(C(C2=CC=C(OCO3)C3=C2)(C4=CC=C(OCO5)C5=C4)O)CC1)OC6=CC=C([N+]([O-])=O)C=C6
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
        
Product Data
Product Data
Instruction
View handling instruction
Biological target:
JZL 184 is a potent, selective and irreversible MAGL inhibitor that blocks 2-Arachidonoylglycerol (2-AG) hydrolysis in brain membranes (IC50 of 8 nM). JZL 184 displays >300-fold selectivity for MAGL over FAAH.
In vitro activity:
In vitro, JZL184 induced a time- and concentration-dependent reduction of A549 cell invasion through Matrigel-coated membranes, which was likewise reversed by AM-251. Reference: Mol Cancer Ther. 2021 May;20(5):787-802. https://pubmed.ncbi.nlm.nih.gov/33632876/
In vivo activity:
Mice given daily injections of high-dose JZL184 (≥16 mg/kg) for 6 days displayed decreased CB1 receptor density and function in the brain, as assessed in [(3)H]SR141716A binding and CP55,940 [(-)-cis-3-[2-hydroxy-4-(1,1-dimethylheptyl)phenyl]-trans-4-(3-hydroxypropyl) cyclohexanol]-stimulated guanosine 5'-O-(3-[(35)S]thio)triphosphate binding assays, respectively. In contrast, normal CB1 receptor expression and function were maintained following repeated administration of low-dose JZL184 (≤8 mg/kg). Reference: J Pharmacol Exp Ther. 2013 Jun;345(3):492-501. https://pubmed.ncbi.nlm.nih.gov/23412396/
Solvent mg/mL mM
Solubility
DMF 30.0 57.64
DMSO 54.0 103.78
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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 the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Prüser JL, Ramer R, Wittig F, Ivanov I, Merkord J, Hinz B. The Monoacylglycerol Lipase Inhibitor JZL184 Inhibits Lung Cancer Cell Invasion and Metastasis via the CB1 Cannabinoid Receptor. doi: 10.1158/1535-7163.MCT-20-0589. Epub 2021 Feb 25. PMID: 33632876. 2. Ma M, Bai J, Ling Y, Chang W, Xie G, Li R, Wang G, Tao K. Monoacylglycerol lipase inhibitor JZL184 regulates apoptosis and migration of colorectal cancer cells. Mol Med Rep. 2016 Mar;13(3):2850-6. doi: 10.3892/mmr.2016.4829. Epub 2016 Jan 29. PMID: 26847687. 3. Kinsey SG, Wise LE, Ramesh D, Abdullah R, Selley DE, Cravatt BF, Lichtman AH. Repeated low-dose administration of the monoacylglycerol lipase inhibitor JZL184 retains cannabinoid receptor type 1-mediated antinociceptive and gastroprotective effects. J Pharmacol Exp Ther. 2013 Jun;345(3):492-501. doi: 10.1124/jpet.112.201426. Epub 2013 Feb 14. PMID: 23412396; PMCID: PMC3657109. 4. Long JZ, Li W, Booker L, Burston JJ, Kinsey SG, Schlosburg JE, Pavón FJ, Serrano AM, Selley DE, Parsons LH, Lichtman AH, Cravatt BF. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol. 2009 Jan;5(1):37-44. doi: 10.1038/nchembio.129. Epub 2008 Nov 23. PMID: 19029917; PMCID: PMC2605181.
In vitro protocol:
1. Prüser JL, Ramer R, Wittig F, Ivanov I, Merkord J, Hinz B. The Monoacylglycerol Lipase Inhibitor JZL184 Inhibits Lung Cancer Cell Invasion and Metastasis via the CB1 Cannabinoid Receptor. doi: 10.1158/1535-7163.MCT-20-0589. Epub 2021 Feb 25. PMID: 33632876. 2. Ma M, Bai J, Ling Y, Chang W, Xie G, Li R, Wang G, Tao K. Monoacylglycerol lipase inhibitor JZL184 regulates apoptosis and migration of colorectal cancer cells. Mol Med Rep. 2016 Mar;13(3):2850-6. doi: 10.3892/mmr.2016.4829. Epub 2016 Jan 29. PMID: 26847687.
In vivo protocol:
1. Kinsey SG, Wise LE, Ramesh D, Abdullah R, Selley DE, Cravatt BF, Lichtman AH. Repeated low-dose administration of the monoacylglycerol lipase inhibitor JZL184 retains cannabinoid receptor type 1-mediated antinociceptive and gastroprotective effects. J Pharmacol Exp Ther. 2013 Jun;345(3):492-501. doi: 10.1124/jpet.112.201426. Epub 2013 Feb 14. PMID: 23412396; PMCID: PMC3657109. 2. Long JZ, Li W, Booker L, Burston JJ, Kinsey SG, Schlosburg JE, Pavón FJ, Serrano AM, Selley DE, Parsons LH, Lichtman AH, Cravatt BF. Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects. Nat Chem Biol. 2009 Jan;5(1):37-44. doi: 10.1038/nchembio.129. Epub 2008 Nov 23. PMID: 19029917; PMCID: PMC2605181.
1: Lysenko LV, Kim J, Henry C, Tyrtyshnaia A, Kohnz RA, Madamba F, Simon GM, Kleschevnikova NE, Nomura DK, Ezekowitz RA, Kleschevnikov AM. Monoacylglycerol Lipase Inhibitor JZL184 Improves Behavior and Neural Properties in Ts65Dn Mice, a Model of Down Syndrome. PLoS One. 2014 Dec 4;9(12):e114521. doi: 10.1371/journal.pone.0114521. eCollection 2014. PubMed PMID: 25474204. 2: Khasabova IA, Yao X, Paz J, Lewandowski CT, Lindberg AE, Coicou L, Burlakova N, Simone DA, Seybold VS. JZL184 is anti-hyperalgesic in a murine model of cisplatin-induced peripheral neuropathy. Pharmacol Res. 2014 Oct 7;90C:67-75. doi: 10.1016/j.phrs.2014.09.008. [Epub ahead of print] PubMed PMID: 25304184. 3: Ma L, Wang L, Yang F, Meng XD, Wu C, Ma H, Jiang W. Disease-modifying effects of RHC80267 and JZL184 in a pilocarpine mouse model of temporal lobe epilepsy. CNS Neurosci Ther. 2014 Oct;20(10):905-15. doi: 10.1111/cns.12302. Epub 2014 Jul 3. PubMed PMID: 24989980. 4: Fernández-Suárez D, Celorrio M, Riezu-Boj JI, Ugarte A, Pacheco R, González H, Oyarzabal J, Hillard CJ, Franco R, Aymerich MS. The monoacylglycerol lipase inhibitor JZL184 is neuroprotective and alters glial cell phenotype in the chronic MPTP mouse model. Neurobiol Aging. 2014 Nov;35(11):2603-16. doi: 10.1016/j.neurobiolaging.2014.05.021. Epub 2014 May 28. PubMed PMID: 24973119. 5: Seillier A, Dominguez Aguilar D, Giuffrida A. The dual FAAH/MAGL inhibitor JZL195 has enhanced effects on endocannabinoid transmission and motor behavior in rats as compared to those of the MAGL inhibitor JZL184. Pharmacol Biochem Behav. 2014 Sep;124:153-9. doi: 10.1016/j.pbb.2014.05.022. Epub 2014 Jun 6. PubMed PMID: 24911644; PubMed Central PMCID: PMC4150743. 6: Kinsey SG, Wise LE, Ramesh D, Abdullah R, Selley DE, Cravatt BF, Lichtman AH. Repeated low-dose administration of the monoacylglycerol lipase inhibitor JZL184 retains cannabinoid receptor type 1-mediated antinociceptive and gastroprotective effects. J Pharmacol Exp Ther. 2013 Jun;345(3):492-501. doi: 10.1124/jpet.112.201426. Epub 2013 Feb 14. PubMed PMID: 23412396; PubMed Central PMCID: PMC3657109. 7: Kerr DM, Harhen B, Okine BN, Egan LJ, Finn DP, Roche M. The monoacylglycerol lipase inhibitor JZL184 attenuates LPS-induced increases in cytokine expression in the rat frontal cortex and plasma: differential mechanisms of action. Br J Pharmacol. 2013 Jun;169(4):808-19. doi: 10.1111/j.1476-5381.2012.02237.x. PubMed PMID: 23043675; PubMed Central PMCID: PMC3687661. 8: Crow JA, Bittles V, Borazjani A, Potter PM, Ross MK. Covalent inhibition of recombinant human carboxylesterase 1 and 2 and monoacylglycerol lipase by the carbamates JZL184 and URB597. Biochem Pharmacol. 2012 Nov 1;84(9):1215-22. doi: 10.1016/j.bcp.2012.08.017. Epub 2012 Aug 27. PubMed PMID: 22943979; PubMed Central PMCID: PMC3470872. 9: Woodhams SG, Wong A, Barrett DA, Bennett AJ, Chapman V, Alexander SP. Spinal administration of the monoacylglycerol lipase inhibitor JZL184 produces robust inhibitory effects on nociceptive processing and the development of central sensitization in the rat. Br J Pharmacol. 2012 Dec;167(8):1609-19. doi: 10.1111/j.1476-5381.2012.02179.x. PubMed PMID: 22924700; PubMed Central PMCID: PMC3525864. 10: Ghosh S, Wise LE, Chen Y, Gujjar R, Mahadevan A, Cravatt BF, Lichtman AH. The monoacylglycerol lipase inhibitor JZL184 suppresses inflammatory pain in the mouse carrageenan model. Life Sci. 2013 Mar 19;92(8-9):498-505. doi: 10.1016/j.lfs.2012.06.020. Epub 2012 Jun 28. PubMed PMID: 22749865; PubMed Central PMCID: PMC3717616. 11: Sciolino NR, Zhou W, Hohmann AG. 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. Pharmacol Res. 2011 Sep;64(3):226-34. doi: 10.1016/j.phrs.2011.04.010. Epub 2011 May 11. PubMed PMID: 21600985; PubMed Central PMCID: PMC3140828. 12: Björklund E, Norén E, Nilsson J, Fowler CJ. Inhibition of monoacylglycerol lipase by troglitazone, N-arachidonoyl dopamine and the irreversible inhibitor JZL184: comparison of two different assays. Br J Pharmacol. 2010 Dec;161(7):1512-26. doi: 10.1111/j.1476-5381.2010.00974.x. PubMed PMID: 20735405; PubMed Central PMCID: PMC3010564. 13: Pan B, Wang W, Long JZ, Sun D, Hillard CJ, Cravatt BF, Liu QS. 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. J Pharmacol Exp Ther. 2009 Nov;331(2):591-7. doi: 10.1124/jpet.109.158162. Epub 2009 Aug 7. PubMed PMID: 19666749; PubMed Central PMCID: PMC2775254.

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A‑971432

A‑971432