Chemistry:Oleamide

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Short description: Chemical compound
Oleamide
Oleamide.svg
Names
Preferred IUPAC name
(9Z)-Octadec-9-enamide
Other names
oleoyl-amide
Oleylamide
9-Octadecenamide
(Z)-9-Octadecenamide
9,10-Octadecenoamide
Oleic acid amide
Cis-9,10-octadecenoamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 206-103-9
UNII
Properties
C18H35NO
Molar mass 281.484 g·mol−1
Appearance Creamy solid[1]
Density 0.879 g/cm3
Melting point 70 °C (158 °F; 343 K)<[2]
Boiling point > 200 °C (392 °F; 473 K)[1]
Insoluble[1]
Hazards
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial 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).
Infobox references

Oleamide is an organic compound with the formula CH
3(CH
2)
7CH=CH(CH
2)
7CONH
2.[3] It is the amide derived from the fatty acid oleic acid. It is a colorless waxy solid and occurs in nature. Sometimes labeled as a fatty acid primary amide (FAPA), it is biosynthesized from N-oleoylglycine.[4]

Biochemical and medical aspects

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 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][9] Some in-vitro studies show that cis-oleamide is an agonist for the cannabinoid receptor CB-1 with an affinity around 8 micromolar.[10] However, given oleamide's relatively low affinity for CB-1 and uncertainty about the concentration and biological role of oleamide in-vivo, it has been argued that it is premature to classify oleamide as an endocannabinoid.[11] At larger doses oleamide can lower the body temperature of mice by about 2 degrees, with the effect lasting about two hours.[9] The mechanism for this remains unknown.[9]

Oleamide has been found to enhance PPARα-dependent increase in doublecortin, a marker of neurogenesis in the hippocampus[12]

Oleamide is rapidly metabolized by fatty acid amide hydrolase (FAAH), the same enzyme that metabolizes anandamide.[13] It has been postulated that some effects of oleamide are caused by increased concentrations of anandamide brought about through the inhibition of FAAH.[9]

It has been claimed that oleamide increases the activity of choline acetyltransferase, an enzyme that is critical in the production of acetylcholine.[14]

Other occurrences

Oleamide has been found in Ziziphus jujuba, also known as Jujube fruit.[14]

Synthetic oleamide has a variety of industrial uses including as a slip agent, a lubricant, and a corrosion inhibitor.[15]

Oleamide was found to be leaching out of polypropylene plastics in laboratory experiments, affecting experimental results.[16] Since polypropylene is used in a wide number of food containers such as those for yogurt, the problem is being studied.[17]

Oleamide is "one of the most frequent non-cannabinoid ingredients associated with Spice products."[18] Analysis of 44 products synthetic cannabinoid revealed oleamide in 7 of the products tested.[19]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 Oleamide at chemicalland21.com
  2. ↑ "(9Z)-9-Octadecenamide | C18H35NO | ChemSpider". http://www.chemspider.com/Chemical-Structure.4446508.html. 
  3. ↑ "Oleamide". https://pubchem.ncbi.nlm.nih.gov/compound/Oleamide. 
  4. ↑ 4.0 4.1 McKinney, Michele K.; Cravatt, Benjamin F. (June 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. PMID 15952893. 
  5. ↑ Cravatt, B.; Prospero-Garcia, O; Siuzdak, G; Gilula, N.; Henriksen, S.; Boger, D.; Lerner, R. (9 June 1995). "Chemical characterization of a family of brain lipids that induce sleep". Science 268 (5216): 1506–1509. doi:10.1126/science.7770779. PMID 7770779. Bibcode: 1995Sci...268.1506C. 
  6. ↑ Methods of treating anxiety and mood disorders with oleamide – US Patent 6359010
  7. ↑ Mechoulam, Raphael; Fride, Ester; Hanu, Lumir; Sheskin, Tzviel; Bisogno, Tiziana; Di Marzo, Vincenzo; Bayewitch, Michael; Vogel, Zvi (September 1997). "Anandamide may mediate sleep induction". Nature 389 (6646): 25–26. doi:10.1038/37891. PMID 9288961. Bibcode: 1997Natur.389R..25M. 
  8. ↑ Fedorova, I; Hashimoto, A; Fecik, RA; Hedrick, MP; Hanus, LO; Boger, DL; Rice, KC; Basile, AS (October 2001). "Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems". The Journal of Pharmacology and Experimental Therapeutics 299 (1): 332–42. PMID 11561096. 
  9. ↑ 9.0 9.1 9.2 9.3 Hiley, C. Robin; Hoi, Pui Man (13 April 2007). "Oleamide: A Fatty Acid Amide Signaling Molecule in the Cardiovascular System?: OLEAMIDE". Cardiovascular Drug Reviews 25 (1): 46–60. doi:10.1111/j.1527-3466.2007.00004.x. PMID 17445087. 
  10. ↑ Leggett, JD; Aspley, S; Beckett, SR; D'Antona, AM; Kendall, DA; Kendall, DA (January 2004). "Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors.". British Journal of Pharmacology 141 (2): 253–62. doi:10.1038/sj.bjp.0705607. PMID 14707029. 
  11. ↑ Fowler, Christopher J (January 2004). "Oleamide: a member of the endocannabinoid family?: Commentary". British Journal of Pharmacology 141 (2): 195–196. doi:10.1038/sj.bjp.0705608. PMID 14691053. 
  12. ↑ Roy, Avik; Kundu, Madhuchhanda; Chakrabarti, Sudipta; Patel, Dhruv R; Pahan, Kalipada (December 2021). "Oleamide, a Sleep-Inducing Supplement, Upregulates Doublecortin in Hippocampal Progenitor Cells via PPARα". J Alzheimers Dis. 84 (4): 1747–1762. doi:10.3233/JAD-215124. PMID 34744082. 
  13. ↑ Maurelli, Stefano; Bisogno, Tiziana; De Petrocellis, Luciano; Di Luccia, Aldo; Marino, Gennaro; Di Marzo, Vincenzo (11 December 1995). "Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'". FEBS Letters 377 (1): 82–86. doi:10.1016/0014-5793(95)01311-3. PMID 8543025. 
  14. ↑ 14.0 14.1 Heo, Ho-Jin; Park, Young-June; Suh, Young-Min; Choi, Soo-Jung; Kim, Mi-Jeong; Cho, Hong-Yon; Chang, Yun-Jeong; Hong, Bumshik et al. (January 2003). "Effects of Oleamide on Choline Acetyltransferase and Cognitive Activities". Bioscience, Biotechnology, and Biochemistry 67 (6): 1284–1291. doi:10.1271/bbb.67.1284. PMID 12843655. 
  15. ↑ Surfactants : Westco Oleamide a Slip Agent In Polyethylene Films
  16. ↑ McDonald, G. R.; Hudson, A. L.; Dunn, S. M. J.; You, H.; Baker, G. B.; Whittal, R. M.; Martin, J. W.; Jha, A. et al. (7 November 2008). "Bioactive Contaminants Leach from Disposable Laboratory Plasticware". Science 322 (5903): 917. doi:10.1126/science.1162395. PMID 18988846. Bibcode: 2008Sci...322..917M. 
  17. ↑ Mittelstaedt, Martin (6 November 2008). "Researchers Raise Alarm After Chemical Leak Found In Common Plastic". Globe and Mail. https://www.theglobeandmail.com/news/national/researchers-raise-alarm-after-chemical-leak-found-in-common-plastic/article1065340/. 
  18. ↑ Fattore, Liana; Fratta, Walter (21 September 2011). "Beyond THC: The New Generation of Cannabinoid Designer Drugs". Frontiers in Behavioral Neuroscience 5: 60. doi:10.3389/fnbeh.2011.00060. PMID 22007163. 
  19. ↑ Uchiyama, Nahoko; Kikura-Hanajiri, Ruri; Ogata, Jun; Goda, Yukihiro (May 2010). "Chemical analysis of synthetic cannabinoids as designer drugs in herbal products". Forensic Science International 198 (1–3): 31–38. doi:10.1016/j.forsciint.2010.01.004. PMID 20117892. 



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