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J3455

Sigma-Aldrich

JZL 184 hydrate

≥97% (HPLC)

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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

Quality Level

100

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

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yihui Cui et al.
eLife, 5, e13185-e13185 (2016-02-28)
Synaptic plasticity is a cardinal cellular mechanism for learning and memory. The endocannabinoid (eCB) system has emerged as a pivotal pathway for synaptic plasticity because of its widely characterized ability to depress synaptic transmission on short- and long-term scales. Recent
Marie Smith et al.
PloS one, 10(9), e0136546-e0136546 (2015-09-29)
The endocannabinoid system is expressed in bone, although its role in the regulation of bone growth is controversial. Many studies have examined the effect of endocannabinoids directly on osteoclast function, but few have examined their role in human osteoblast function
Olga Karpińska et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 312(6), R883-R893 (2017-03-31)
Recent evidence suggests that endocannabinoids acting via cannabinoid CB

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