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

Physicochemical Properties

Molecular Formula	C24H35NO2
Molecular Weight	369.54
Exact Mass	369.266
CAS #	876305-42-9
PubChem CID	25021164
Appearance	Colorless to light yellow liquid
Density	1.0±0.1 g/cm3
Boiling Point	492.9±34.0 °C at 760 mmHg
Flash Point	185.2±18.0 °C
Vapour Pressure	0.0±1.3 mmHg at 25°C
Index of Refraction	1.524
LogP	7.89
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	15
Heavy Atom Count	27
Complexity	549
Defined Atom Stereocenter Count	0
SMILES	CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCN1C(=O)C=CC1=O
InChi Key	GZNZRHSGGQUYAP-DOFZRALJSA-N
InChi Code	InChI=1S/C24H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-25-23(26)20-21-24(25)27/h6-7,9-10,12-13,15-16,20-21H,2-5,8,11,14,17-19,22H2,1H3/b7-6-,10-9-,13-12-,16-15-
Chemical Name	1-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenyl]pyrrole-2,5-dione
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	IC50: 140 nM (MAGL)[1]
ln Vitro	A potential MAGL inhibitor that can be utilized to control the effects of 2-arachidonyl glycerol (2-AG) is N-arachidonyl maleimide. N-Arachidonyl maleimide raises the brain's natural amounts of 2-AG. At a comparatively modest concentration (IC50, 140 nM), N-arachidonyl maleimide inhibits the breakdown of 2-AG mediated by the cerebellar membrane[1].
ln Vivo	2-AG (1, 3, and 10 mg/kg) induces substantial and dose-dependent hypothermia, antinociception, and catalepsy when paired with a 1 mg/kg dosage of N-Arachidonyl maleimide[1].
References	[1]. 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]. 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.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (270.61 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.77 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (6.77 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.77 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.7061 mL	13.5303 mL	27.0607 mL
	5 mM	0.5412 mL	2.7061 mL	5.4121 mL
	10 mM	0.2706 mL	1.3530 mL	2.7061 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.