(9Z)-octadec-9-enamide

• ChemBase ID: 133078
• Molecular Formular: C18H35NO
• Molecular Mass: 281.4766
• Monoisotopic Mass: 281.27186475
• SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)N
• Canonical SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)N
• InChI: 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-
• InChIKey: FATBGEAMYMYZAF-KTKRTIGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9Z)-octadec-9-enamide
• IUPAC Traditional name: oleamide
• Synonyms: Oleylamide; Crodamide O; Adogen 73; Neutron (amide); Kemamide U; Unislip 1759; Oleamide; cis-9,10-Octadecenoamide; cis-9-Octadecenamide; Oleic acid amide; Oleamide

Database IDs

• CAS Number: 301-02-0
• EC Number: 206-103-9
• MDL Number: MFCD00053638
• PubChem SID: 24897957; 162227355
• PubChem CID: 5283387

CALCULATED PROPERTIES

• Acid pKa: 16.920465
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 5.9768553
• LogD (pH = 7.4): 5.9768558
• Log P: 5.9768558
• Molar Refractivity: 89.2244 cm^3
• Polarizability: 34.883404 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Clear Colourless Solution 5mg/0.1 ml of Chloroform
• Apperance: White Solid
• Melting Point: 76-78°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥99%

DETAILS

Sigma Aldrich - O2136

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

Toronto Research Chemicals - O255000

A brain lipid that induces physiological sleep at nanomolar quantities when injected into rats. This lipid may represent a new class of biological signaling molecules.

REFERENCES

• Kim, M., et al.: Drug Delivery, 15, 373 (2008)
• Burstein, S., et al.: Bioorg. Med. Chem., 16, 9644 (2008)
• Sudhahar, V., et al.: Eur. J. Pharmacol., 607, 143 (2008)