4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate hydrate

• ChemBase ID: 155790
• Molecular Formular: C27H26N2O10
• Molecular Mass: 538.50274
• Monoisotopic Mass: 538.15874504
• SMILES: c1cc(ccc1[N+](=O)[O-])OC(=O)N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O.O
• Canonical SMILES: O=C(N1CCC(CC1)C(c1ccc2c(c1)OCO2)(c1ccc2c(c1)OCO2)O)Oc1ccc(cc1)[N+](=O)[O-].O
• InChI: 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
• InChIKey: HNSBVGMOKGQJLT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate hydrate
• IUPAC Traditional name: 4-nitrophenyl 4-[bis(2H-1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate hydrate
• Synonyms: JZL 184 hydrate; JZL184 hydrate

Database IDs

• MDL Number: MFCD12912421
• PubChem SID: 162249928
• PubChem CID: 71312223

CALCULATED PROPERTIES

• Acid pKa: 13.1246605
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 3.9531872
• LogD (pH = 7.4): 3.9531865
• Log P: 3.9531872
• Molar Refractivity: 132.0473 cm^3
• Polarizability: 51.068157 Å^3
• Polar Surface Area: 132.51 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: light yellow powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C27H24N2O9 · xH2O

DETAILS

Sigma Aldrich - J3455

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.