Oleamide

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Oleamide
Oleamide.svg
Names
IUPAC name
(Z)-Octa-9-decenamide
Other names
Oleylamide
9-Octadecenamide
(Z)-9-Octadecenamide
9,10-Octadecenoamide
Oleic acid amide
Cis-9,10-octadecenoamide
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.550
EC Number 206-103-9
UNII
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
Flammability code 0: Will not burn. E.g., water Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point > 200 °C (392 °F; 473 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 be 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]

  1. ^ a b c d Oleamide at chemicalland21.com
  2. ^ http://www.chemicalbook.com/ProductChemicalPropertiesCB3238286_EN.htm
  3. ^ http://www.chemspider.com/Chemical-Structure.4446508.html
  4. ^ 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. 
  5. ^ 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. 
  6. ^ Methods of treating anxiety and mood disorders with oleamide - US Patent 6359010
  7. ^ 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. 
  8. ^ 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. 
  9. ^ Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films Archived January 27, 2007, at the Wayback Machine.
  10. ^ McDonald, RG.; et al. (2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware". Science. 322 (5903): 917. doi:10.1126/science.1162395. PMID 18988846. 
  11. ^ Mittelstaedt, Martin (6 November 2008). "Researchers Raise Alarm After Chemical Leak Found In Common Plastic". Globe and Mail. Retrieved 10 June 2013. 
  12. ^ 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.