O2136

Oleamide

≥99% (TLC), powder, sleep-inducing brain lipid

• Synonym(s): cis-9,10-Octadecenoamide, cis-9-Octadecenamide, Oleic acid amide
• Empirical Formula (Hill Notation): C₁₈H₃₅NO
• CAS Number: 301-02-0
• Molecular Weight: 281.48
• EC Number: 206-103-9
• MDL number: MFCD00053638
• UNSPSC Code: 12352200
• PubChem Substance ID: 24897957
• NACRES: NA.77

Properties

• product name: Oleamide, ≥99%
• Assay: ≥99%
• drug control: regulated under CDSA - not available from Sigma-Aldrich Canada
• storage temp.: −20°C
• SMILES string: CCCCCCCC\C=C/CCCCCCCC(N)=O
• 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

Description

General description

Oleamide is a lipid or a brain fatty acid, that is found in the CSF (cerebrospinal fluid). It is originally obtained from the cerebrospinal fluid of cats, that are sleep-deprived.

Application

Oleamide has been used as a supplement in glucose and galactose media to prevent the rescue of galactose-induced Leigh syndrome (LS).

Biochem/physiol Actions

Oleamide has the ability to stimulate sleep. It possess several properties, like cannabinoid-like activity. Oleamide can also disable the communication, facilitated by gap junction between rat glial cells.

Sleep-inducing brain lipid, which allosterically modulates GABA_A receptors and potentiates 5-HT₇ serotonin receptor responses. Selective endogenous agonist of rat and human CB1 cannabinoid receptor.

Safety Information

• Hazard Statements: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): 404.6 °F - closed cup
• Flash Point(C): 207 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves