Oleamide
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| Names | |
|---|---|
| IUPAC name
(Z)-Octa-9-decenamide
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| Other names
Oleylamide
9-Octadecenamide (Z)-9-Octadecenamide 9,10-Octadecenoamide Oleic acid amide Cis-9,10-octadecenoamide |
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| Identifiers | |
301-02-0  |
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| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:116314  |
| ChEMBL | ChEMBL15927 |
| ChemSpider | 4446508 |
| ECHA InfoCard | 100.005.550 |
| EC Number | 206-103-9 |
| 284 | |
| PubChem | 5283387 |
| UNII | 7L25QK8BWO |
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| Properties | |
| C18H35NO | |
| Molar mass | 281.48 g·mol−1 |
| Appearance | Creamy solid[1] |
| Density | 0.879 g/cm3 |
| Melting point | 70 °C (158 °F; 343 K)[2][3] |
| Boiling point | > 200 °C (392 °F; 473 K)[1] |
| Insoluble[1] | |
| Hazards | |
| NFPA 704 | |
| Flash point | > 200 °C (392 °F; 473 K)[1] |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |
Oleamide is an organic compound with the formula CH3(CH2)7CH=CH(CH2)7C(O)NH2. It is the amide derived from the fatty acid oleic acid. It is a colorless waxy solid. It is naturally occurring. Sometimes labeled as a fatty acid primary amide (FAPA), it is biosynthesized from N-oleoylglycine.[4]
Biochemical and medical aspects[edit]
In terms of natural occurrence, oleamide was first detected in human plasma. It was later shown to accumulate in the cerebrospinal fluid during sleep deprivation and induces sleep in animals.[4][5]
It has been considered as a potential treatment for mood and sleep disorders, as well as cannabinoid-regulated depression.[6][7]
In terms of its sleep inducing effects, it is speculated that oleamide interacts with multiple neurotransmitter systems.[8]
Other occurrences[edit]
Synthetic oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.[9]
Oleamide was found to leaking out of polypropylene plastics in laboratory experiments, affecting experimental results.[10] Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.[11]
Analysis of 44 products containing synthetic cannabinoid drugs marketed as "herbal incense" revealed oleamide in 7 of the products tested.[12]
See also[edit]
References[edit]
- ^ a b c d Oleamide at chemicalland21.com
- ^ http://www.chemicalbook.com/ProductChemicalPropertiesCB3238286_EN.htm
- ^ http://www.chemspider.com/Chemical-Structure.4446508.html
- ^ a b McKinney, Michele K.; Cravatt, Benjamin F. (2005). "Structure and Function of Fatty Acid Amide Hydrolase". Annual Review of Biochemistry. 74 (1): 411–432. doi:10.1146/annurev.biochem.74.082803.133450. ISSN 0066-4154.
- ^ Cravatt BF, et al. (June 1995). "Chemical characterization of a family of brain lipids that induce sleep". Science. 268 (5216): 1506–9. doi:10.1126/science.7770779. PMID 7770779.
- ^ Methods of treating anxiety and mood disorders with oleamide - US Patent 6359010
- ^ Raphael Mechoulam, Ester Fride, Lumír Ondřej Hanuš, Tzviel Sheskin, Tiziana Bisogno, Vincenzo Di Marzo, Michael Bayewitch and Zvi Vogel (1997). "Anandamide may mediate sleep induction". Nature. 389 (6646): 25–26. doi:10.1038/37891. PMID 9288961.
- ^ 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 Archived January 27, 2007, at the Wayback Machine.
- ^ McDonald, RG.; et al. (2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware". Science. 322 (5903): 917. doi:10.1126/science.1162395. PMID 18988846.
- ^ Mittelstaedt, Martin (6 November 2008). "Researchers Raise Alarm After Chemical Leak Found In Common Plastic". Globe and Mail. Retrieved 10 June 2013.
- ^ Uchiyama, Nahoko; Kikura-Hanajiri, Ruri; Ogata, Jun; Goda, Yukihiro (2010). "Chemical analysis of synthetic cannabinoids as designer drugs in herbal products". Forensic Science International. 198 (1–3): 31–8. doi:10.1016/j.forsciint.2010.01.004. PMID 20117892.
