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Oleamide[1]
Identifiers
CAS number 301-02-0 Yes check.svgY
PubChem 5283387
EC number 206-103-9
SMILES
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
NFPA 704.svg
0
1
0
Flash point >200 °C
 Yes check.svgY (what is this?)  (verify)
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.[3][4]

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] Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist. In addition, oleamide potentiates several serotonin receptors and the GABA(A) receptor, and inhibits gap junction communication.

Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.[6]

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 [7].

Oleamide was found by researchers to be leaking out of polypropylene plastics used in laboratory experiments, affecting experimental results.[8] Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.[9]

Recreational use

There is no documented evidence of Oleamide being used specifically as a recreational drug. However, it was found in large quantities in the smoking blends "Smoke" and "Skunk" alongside the synthetic cannabinoid JWH-018 [10].

See also

References

  1. ^ Oleamide at chemicalland21.com
  2. ^ 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:10.1006/exnr.2001.7792. 
  3. ^ Methods of treating anxiety and mood disorders with oleamide - US Patent 6359010
  4. ^ 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:10.1038/37891. 
  5. ^ 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. 
  6. ^ Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films
  7. ^ Cravatt BF, Prospero-Garcia O, Siuzdak G, Gilula NB, Henriksen SJ, Boger DL, Lerner RA (June 1995). "Chemical characterization of a family of brain lipids that induce sleep". Science (journal) 268 (5216): 1506–9. PMID 7770779. http://www.sciencemag.org/cgi/pmidlookup?view=long&pmid=7770779. 
  8. ^ McDonald, RG. et al (2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware". Science 322 (5903): 917. doi:10.1126/science.1162395. PMID 18988846. 
  9. ^ Mittelstaedt, Martin (6 November 2008). "Researchers Raise Alarm After Chemical Leak Found In Common Plastic". Globe and Mail. http://www.ewg.org/node/27344. Retrieved 28 December 2009. 
  10. ^ ‘Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? http://www.synchronium.net/wp-content/uploads/2009/02/spiceanalysis.pdf







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