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
301-02-0 YesY
ChEBI CHEBI:116314 N
ChEMBL ChEMBL15927 YesY
ChemSpider 4446508 YesY
EC Number 206-103-9
284
Jmol 3D model Interactive image
PubChem 5283387
UNII 7L25QK8BWO YesY
  • InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9- YesY
    Key: FATBGEAMYMYZAF-KTKRTIGZSA-N YesY
  • InChI=1/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
    Key: FATBGEAMYMYZAF-KTKRTIGZBR
  • O=C(N)CCCCCCC\C=C/CCCCCCCC
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]
Vapor pressure {{{value}}}
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.[citation needed]

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. 1.0 1.1 1.2 Oleamide at chemicalland21.com
  2. http://www.chemicalbook.com/ProductChemicalPropertiesCB3238286_EN.htm
  3. http://www.chemspider.com/Chemical-Structure.4446508.html
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  5. Methods of treating anxiety and mood disorders with oleamide - US Patent 6359010
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  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
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