N-Arachidonyl maleimide

Modify Date: 2024-01-08 18:14:21

N-Arachidonyl maleimide Structure
N-Arachidonyl maleimide structure
Common Name N-Arachidonyl maleimide
CAS Number 876305-42-9 Molecular Weight 369.540
Density 1.0±0.1 g/cm3 Boiling Point 492.9±34.0 °C at 760 mmHg
Molecular Formula C24H35NO2 Melting Point N/A
MSDS Chinese USA Flash Point 185.2±18.0 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of N-Arachidonyl maleimide


N-Arachidonyl maleimide is a potent, irreversible inhibitor of monoacylglycerol lipase (MAGL) with an IC50 value of 140 nM[1].

 Names

Name N-Arachidonyl maleimide,1-(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraen-1-yl-1H-pyrrole-2,5-dione
Synonym More Synonyms

 N-Arachidonyl maleimide Biological Activity

Description N-Arachidonyl maleimide is a potent, irreversible inhibitor of monoacylglycerol lipase (MAGL) with an IC50 value of 140 nM[1].
Related Catalog
Target

IC50: 140 nM (MAGL)[1]

In Vitro N-Arachidonyl maleimide is a putative MAGL inhibitor, which can be used for modulation of the effects of 2-arachidonyl glycerol (2-AG). N-Arachidonyl maleimide increases endogenous levels of 2-AG in the brain. N-Arachidonyl maleimide prevents cerebellar membrane-mediated degradation of 2-AG at a relatively low concentration (IC50, 140 nM)[1].
In Vivo When combined with a 1 mg/kg dose of N-Arachidonyl maleimide, 2-AG (1, 3, and 10 mg/kg) produces significant and dose-dependent hypothermia, inhibition of locomotor activity, antinociception, and catalepsy[1].
References

[1]. Susanna M Saario, et al. Characterization of the Sulfhydryl-Sensitive Site in the Enzyme Responsible for Hydrolysis of 2-arachidonoyl-glycerol in Rat Cerebellar Membranes. Chem Biol. 2005 Jun;12(6):649-56.

[2]. James J Burston, et al. N-arachidonyl Maleimide Potentiates the Pharmacological and Biochemical Effects of the Endocannabinoid 2-arachidonylglycerol Through Inhibition of Monoacylglycerol Lipase. J Pharmacol Exp Ther. 2008 Nov;327(2):546-53.

 Chemical & Physical Properties

Density 1.0±0.1 g/cm3
Boiling Point 492.9±34.0 °C at 760 mmHg
Molecular Formula C24H35NO2
Molecular Weight 369.540
Flash Point 185.2±18.0 °C
Exact Mass 369.266785
PSA 37.38000
LogP 7.89
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.524

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H317
Precautionary Statements P280
RIDADR NONH for all modes of transport

 Articles2

More Articles
Crystal structure of the human monoacylglycerol lipase, a key actor in endocannabinoid signaling.

ChemBioChem. 11 , 218-27, (2010)

2-Arachidonoylglycerol plays a major role in endocannabinoid signaling, and is tightly regulated by the monoacylglycerol lipase (MAGL). Here we report the crystal structure of human MAGL. The protein ...

Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes.

Chem. Biol. 12 , 649-56, (2005)

We have previously reported that the endocannabinoid, 2-arachidonoyl-glycerol (2-AG), is hydrolyzed in rat cerebellar membranes by monoglyceride lipase (MGL)-like enzymatic activity. The present study...

 Synonyms

1H-Pyrrole-2,5-dione, 1-[(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraen-1-yl]-
1-[(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraen-1-yl]-1H-pyrrole-2,5-dione
1-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraen-1-yl]-1H-pyrrole-2,5-dione
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