N-Arachidonyl maleimide

Names

[ Name ]:
N-Arachidonyl maleimide

[Synonym ]:
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

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]:

Signaling Pathways >> Metabolic Enzyme/Protease >> MAGL

Research Areas >> Metabolic Disease

[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

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H317

[ Precautionary Statements ]:
P280

[ RIDADR ]:
NONH for all modes of transport

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...