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| Oleamide1 | |
|---|---|
 |
|
| IUPAC name | (Z)-Octa-9-decenamide |
| Other names | Oleylamide 9-Octadecenamide (Z)-9-Octadecenamide 9,10-Octadecenoamide Oleic acid amide |
| Identifiers | |
| CAS number | 301-02-0 |
| PubChem | |
| EINECS number | |
| SMILES |
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| Properties | |
| Molecular formula | C18H35NO |
| Molar mass | 281.48 g mol−1 |
| Appearance | Creamy solid |
| Density | 2.1 g/cm3 |
| Melting point |
102-104 °C |
| Boiling point |
>200 °C |
| Solubility in water | Insoluble |
| Hazards | |
| NFPA 704 |
 0
1
0
|
| Flash point | >200 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
|
Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals.2 It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression.34
The mechanism of action of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems.5 While structurally related to the endogenous cannabinoid anandamide, the ability of oleamide to bind the cannabinoid receptor CB1 is controversial.
Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.6
Oleamide was discovered and characterized by Benjamin Cravatt III and Richard Lerner at The Scripps Research Institute in La Jolla, CA.dubious
Oleamide was found by researchers to be leaking out of polypropylene plastics used in laboratory experiments, affecting experimental results.7 Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.8
See also
References
- ^ Oleamide at chemicalland21.com
- ^ Salvador Huitron-Resendiz, Lhys Gombart, Benjamin F. Cravatt, and Steven J. Henriksen (2001). "Effect of Oleamide on Sleep and Its Relationship to Blood Pressure, Body Temperature, and Locomotor Activity in Rats". Experimental Neurology 172: 235–243. doi:.
- ^ Methods of treating anxiety and mood disorders with oleamide - US Patent 6359010
- ^ Raphael Mechoulam, Ester Fride, Lumir Hanu, Tzviel Sheskin, Tiziana Bisogno, Vincenzo Di Marzo, Michael Bayewitch and Zvi Vogel (1997). "Anandamide may mediate sleep induction". Nature 389: 25–26. doi:.
- ^ Fedorova I, Hashimoto A, Fecik RA, et al (2001). "Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems". J. Pharmacol. Exp. Ther. 299 (1): 332–42. PMID 11561096.
- ^ Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films
- ^ McDonald, RG. et al (2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware". Science 322 (5903): 917. doi:. PMID 18988846.
- ^ "globeandmail.com: Researchers raise alarm after chemical leak found in common plastic". www.theglobeandmail.com. Retrieved on 2008-11-10.
Wikipedia content modification information:
- This page was last modified on 12 November 2008, at 19:21.
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