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Oleamide



Oleamide[1]
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 5283387
EINECS number 206-103-9
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)N
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 Insolube
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 disclaimer and references

Oleamide is an endogenous amide of the fatty acid oleic acid. 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 sleep disorders.[3] Additionally, inhibitors of the enzyme fatty acid amide hydrolase, which breaks down oleamide, lead to raised levels of oleamide, inducing sleep.[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] While structurally related to the endogenous cannabinoid anandamide, the ability of oleamide to bind the cannabinoid receptor CB1 is controversial. [6][7][8][9] It is likely that the hypnotic effects of oleamide are caused by elevated endocannabinoid signaling rather than direct interaction of oleamide and cannabinoid receptors.

Synthetically produced oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.[1][10]

Oleamide was discovered and characterized by Benjamin Cravatt III and Richard Lerner at The Scripps Research Institute in La Jolla, CA.

See also

References

  1. ^ a b 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. ^ 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.
  4. ^ Dale L. Boger, Haruhiko Sato, Aaron E. Lerner, Michael P. Hedrick, Robert A. Fecik, Hiroshi Miyauchi, Gordon D. Wilkie, Bryce J. Austin, Matthew P. Patricelli, and Benjamin F. Cravatt (2000). "Exceptionally potent inhibitors of fatty acid amide hydrolase: The enzyme responsible for degradation of endogenous oleamide and anandamide". PNAS 97 (10): 5044-5049.
  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. ^ Leggett JD, Aspley S, Beckett SR, D'Antona AM, Kendall DA, Kendall DA (2004). "Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors". Br. J. Pharmacol. 141 (2): 253-62. doi:10.1038/sj.bjp.0705607. PMID 14707029.
  7. ^ "Oleamide: a member of the endocannabinoid family?". Br J Pharmacol. PMID 14691053. Retrieved on 2007-06-12.
  8. ^ "Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo". J Pharmacol Exp Ther.. PMID 12065702. Retrieved on 2007-06-14.
  9. ^ "The palmitoylethanolamide and oleamide enigmas : are these two fatty acid amides cannabimimetic?". Curr Med Chem.. PMID 10469890. Retrieved on 2007-06-14.
  10. ^ Westco product information
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Oleamide". A list of authors is available in Wikipedia.
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