1-(icosa-5,8,11,14-tetraen-1-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

• ChemBase ID: 154504
• Molecular Formular: C24H35NO2
• Molecular Mass: 369.5402
• Monoisotopic Mass: 369.26677937
• SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCN1C(=O)C=CC1=O
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCCN1C(=O)C=CC1=O
• InChI: 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
• InChIKey: GZNZRHSGGQUYAP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(icosa-5,8,11,14-tetraen-1-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
• IUPAC Traditional name: 1-(icosa-5,8,11,14-tetraen-1-yl)pyrrole-2,5-dione
• Synonyms: N-Arachidonylmaleimide

Database IDs

• CAS Number: 876305-42-9
• MDL Number: MFCD11521506
• PubChem SID: 162248643
• PubChem CID: 71311881

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.577084
• LogD (pH = 7.4): 6.577084
• Log P: 6.577084
• Molar Refractivity: 120.2041 cm^3
• Polarizability: 44.314014 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• Storage Condition: under inert gas
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 43
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317
• GHS Precautionary statements: P280
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C24H35NO2

DETAILS

Sigma Aldrich - A2984

Biochem/physiol Actions
N-Arachidonylmaleidmide, NAM, is a potent irreversible inhibitor of MAGL, the enzyme predominantly responsible for the degradation of the endocannabinoid 2-arachidonoylglycerol (2-AG). Anandamide and 2-AG are the two endogenous endocannabinoids that activate the cannabinoid receptors CB1 and CB2. Anandamide is predominantly metabolized by fatty acid amide hydrolase (FAAH), whereas monoacylglycerol lipase (MAGL) is thought to be the enzyme primarily responsible for the degradation of 2-AG. It is difficult to separate the activities of the two because most currently available inhibitors of MAGL are not selective, and also inhibit FAAH or other enzymes.