Oleamide

Oleamide is an amide of oleic acid (Cay-90260) and an agonist of cannabinoid 1 (CB1) receptors (Ki = 8.13 µM in a radioligand binding assay). It is selective for CB1 over CB2 receptors, where it inhibits binding of the CB receptor full agonist CP 55,940 by only 42.5% in HEK-293T cells expressing human CB2 receptors when used at a concentration of 100 µM. Oleamide (10 µM) inhibits cAMP accumulation induced by forskolin (Cay-11018) in N1E 115 mouse neuroblastoma cells, an effect that is reversed by the CB1 antagonist SR141716A. Oleamide was first identified in the cerebrospinal fluid of sleep-deprived cats, and it has also been detected in the cerebrospinal fluid of rats and humans. In rats, it induces physiological sleep when administered at doses ranging from 5 to 50 mg and increases food intake when administered into the nucleus accumbens shell, and in group-housed and socially isolated mice, it has anxiolytic-like effects. Oleamide also induces transactivation of PPARalpha, PPARbeta, and PPARgamma and inhibits activity of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA) at concentrations in the low micromolar range.Formal Name: 9Z-octadecenamide. CAS Number: 301-02-0. Synonyms: cis-9-Octadecenamide. Molecular Formula: C18H35NO. Formula Weight: 281.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: >14 mg/ml, DMSO: >20 mg/ml, Ethanol: >22 mg/ml, PBS (pH 7.2): <50 µg/ml. SMILES: CCCCCCCC/C=C\CCCCCCCC(N)=O. InChi Code: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-. InChi Key: FATBGEAMYMYZAF-KTKRTIGZSA-N.