Oleamide

Oleamide
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
301-02-0 YesY
ChEBI CHEBI:116314 N
ChEMBL ChEMBL15927 YesY
ChemSpider 4446508 YesY
EC Number 206-103-9
284
Jmol interactive 3D Image
PubChem 5283387
UNII 7L25QK8BWO YesY
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
0
1
0
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).
N verify (what is YesYN ?)
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.[4] It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression.[5][6]

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.[7] Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist.

Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.[8]

Oleamide was originally characterized as an endogenous bioactive substance, isolated from the cerebrospinal fluid of sleep deprived cats. It was characterised in 1995 by Benjamin Cravatt III and Richard Lerner at The Scripps Research Institute in La Jolla, CA.[9]

Oleamide was found by researchers to be leaking out of polypropylene plastics used 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]

A chemical analysis of 44 products containing synthetic cannabinoid drugs marketed as "herbal incense" revealed oleamide in 7 of the products tested.[12]

See also

References

  1. 1 2 3 4 Oleamide at chemicalland21.com
  2. ↑ http://www.chemicalbook.com/ProductChemicalPropertiesCB3238286_EN.htm
  3. ↑ http://www.chemspider.com/Chemical-Structure.4446508.html
  4. ↑ 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 (1): 235–243. doi:10.1006/exnr.2001.7792. PMID 11681856.
  5. ↑ Methods of treating anxiety and mood disorders with oleamide - US Patent 6359010
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ |url=http://www.wrchem.com/Products/OLEAMIDE.htm |date=20070127054121 Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films Archive copy at the Wayback Machine
  9. ↑ 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.
  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.
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