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Key Documents

A2984

Sigma-Aldrich

N-Arachidonylmaleimide

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C24H35NO2
CAS Number:
Molecular Weight:
369.54
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

assay

≥98% (HPLC)

form

solid

storage condition

under inert gas

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCN1C(=O)C=CC1=O

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-

Inchi Key

GZNZRHSGGQUYAP-DOFZRALJSA-N

Biochem/physiol Actions

N-Arachidonylmaleidmide (NAM) is structurally similar to the MAGL substrate 2-AG and displays a high potency for inhibition of MAGL. It is thought that NAM binds MAGL at the substrate binding site and inhibits enzyme activity through the Michael addition reaction at the Cys201, and to a lesser extent Cys242, residue of MAGL. In cerebellar rat membranes, NAM inhibits MAGL-like activity with an IC50 of 140 nM.
N-Arachidonylmaleidmide, NAM, is a potent irreversible inhibitor of Monoacylglycerol Lipase (MAGL), the enzyme predominantly responsible for the degradation of the endocannabinoid 2-arachidonoylglycerol (2-AG).

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

Exclamation mark

signalword

Warning

hcodes

pcodes

Hazard Classifications

Skin Sens. 1

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


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Susanna M Saario et al.
Chemistry & biology, 12(6), 649-656 (2005-06-25)
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 shows that, like MGL, 2-AG-degrading enzymatic activity is sensitive to inhibition by sulfhydryl-specific reagents. Inhibition studies
Geoffray Labar et al.
Chembiochem : a European journal of chemical biology, 11(2), 218-227 (2009-12-04)
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 crystallizes as a dimer, and despite structural homologies to haloperoxidases and esterases

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