J3455

JZL 184 hydrate

≥97% (HPLC)

• Synonym(s): JZL184 hydrate
• Empirical Formula (Hill Notation): C₂₇H₂₄N₂O₉ · xH₂O
• CAS Number: 1101854-58-3
• Molecular Weight: 520.49 (anhydrous basis)
• MDL number: MFCD12912421
• UNSPSC Code: 12352200
• PubChem Substance ID: 329815406
• NACRES: NA.77

Properties

• Assay: ≥97% (HPLC)
• form: powder
• color: light yellow to yellow-green
• solubility: DMSO: >20 mg/mL
• storage temp.: 2-8°C
• SMILES string: O.OC(C1CCN(CC1)C(=O)Oc2ccc(cc2)[N+]([O-])=O)(c3ccc4OCOc4c3)c5ccc6OCOc6c5
• InChI: 1S/C27H24N2O9.H2O/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;1H2
• InChI key: HNSBVGMOKGQJLT-UHFFFAOYSA-N

Description

Application

JZL 184 hydrate has been used as an inhibitor of monoacylglycerol lipase to study its effect on human osteoblast differentiation and proliferation and postsynaptic neurons.

Biochem/physiol Actions

JZL184 selectively inhibits MAGL, the enzyme predominantly responsible for the degradation of the endocannabinoid 2-arachidonoylglycerol (2-AG). Anandamide and 2-AG are the two endogenous endocannabinoids that activate the cannabinoid receptors CB1 and CB2. Anandamide is predominantly metabolized by fatty acid amide hydrolase (FAAH), whereas monoacylglycerol lipase (MAGL) is thought to be the enzyme primarily responsible for the degradation of 2-AG. It is difficult to separate the activities of the two because most currently available inhibitors of MAGL are not selective, and also inhibit FAAH or other enzymes. JZL 184 is the first selective inhibitor of MAGL with nanomolar portency and over 200-fold selectivity for MAGL vs FAAH. When administered to mice, JZL184 increased levels of 2-arachidonoylglycerol in the brain by about 8-fold, with no effect on levels of anandamide.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable