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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[1]. 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[1][2]. In cerebellar rat membranes, NAM inhibits MAGL-like activity with an IC50 of 140 nM[1].
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.
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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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