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SML0257

Sigma-Aldrich

JZL195

≥98% (HPLC)

Synonym(s):

4-[(3-Phenoxyphenyl)methyl]-1-piperazinecarboxylic acid 4-nitrophenyl ester

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About This Item

Empirical Formula (Hill Notation):
C24H23N3O5
CAS Number:
Molecular Weight:
433.46
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥5 mg/mL at warmed

storage temp.

−20°C

SMILES string

[O-][N+](=O)c1ccc(OC(=O)N2CCN(CC2)Cc3cccc(Oc4ccccc4)c3)cc1

InChI

1S/C24H23N3O5/c28-24(32-22-11-9-20(10-12-22)27(29)30)26-15-13-25(14-16-26)18-19-5-4-8-23(17-19)31-21-6-2-1-3-7-21/h1-12,17H,13-16,18H2

InChI key

QNYRAEKLMNDRFY-UHFFFAOYSA-N

Application

JZL195 has been used:
  • as a selective inhibitor of endocannabinoid (eCB) clearance enzymes to induce in vivo long-term depression at CA3-CA1 synapses and at prelimbic (PrL)-nucleus accumbens (NAc)synapses, to study the neuroprotective action of eCB
  • to inhibit the action of hydrolytic enzymes that limit eCB activity, to study the effect of 2-linoleoylglycerol (2-LG) on the human CB1 receptor activity
  • as a dual fatty acid amide hydrolase (FAAH)/monoacylglycerol lipase (MAGL) inhibitor to study its dose-related antipruritic effect on the serotonin (5-HT)-induced scratching model

Biochem/physiol Actions

JZL195 is a dual inhibitor of FAAH and MAGL.
JZL195 is a potent dual inhibitor of Monoacylglycerol lipase (MAGL) and fatty acid amide hydrolase (FAAH), enzymes that degrade the endocannabinoids 2-arachidonoylglycerol (2-AG) and anandamide (AEA), the endogenous ligands for the cannabinoid G-protein coupled receptors CB1 and CB2. IC50 values are 2 nM for MAGL and 4 nM for FAAH. JZL195 has been shown to inhibit endocannabinoid hydrolysis and elevate 2-AG and AEA levels in vivo.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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