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J3455

Sigma-Aldrich

JZL 184 hydrate

≥97% (HPLC)

Synonyme(s) :

JZL184 hydrate

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About This Item

Formule empirique (notation de Hill):
C27H24N2O9 · xH2O
Numéro CAS:
1101854-58-3
Poids moléculaire :
520.49 (anhydrous basis)
Numéro MDL:
MFCD12912421
Code UNSPSC :
12352200
ID de substance PubChem :
329815406
Nomenclature NACRES :
NA.77

Pureté

≥97% (HPLC)

Forme

powder

Couleur

light yellow to yellow-green

Solubilité

DMSO: >20 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

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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