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Chemical Compound Review

Oleamide     (Z)-octadec-9-enamide

Synonyms: Oleylamide, Oleyramide, ELAIDOYLAMIDE, Slip-eze, Crodamide O, ...
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Disease relevance of Armoslip CP

  • In contrast, oleamide was equally effective in inducing hypothermia in mice lacking the 5-HT(7) receptors as in wild-type mice [1].
  • Here we show that daily intraperitoneal (i.p.) injections of oleamide, a sleep-inducing lipid hormone, weakly inhibited the spontaneous metastasis of BL6 cells [2].
  • Mouse neuroblastoma N(18)TG(2) cells are an excellent model system for the study of oleamide biosynthesis because these cells convert [(14)C]-oleic acid to [(14)C]-oleamide and express PAM in a regulated fashion [3].
  • Oleamide produced equivalent apnea suppression [4].
  • A derivative of oleamide potently inhibits the spontaneous metastasis of mouse melanoma BL6 cells [2].

Psychiatry related information on Armoslip CP


High impact information on Armoslip CP


Chemical compound and disease context of Armoslip CP

  • Taken together, the results show that 5-HT-induced hypothermia is mediated by the 5-HT(7) receptor, and that oleamide may act through an independent mechanism as well as at an allosteric 5-HT(7) receptor site to regulate body temperature [1].
  • In both genotypes, oleamide produced hypomotility, hypothermia, and ptosis, all of which were enhanced in FAAH(-/-) mice, were unaffected by the CB1 antagonist N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-di-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide hydrochloride (SR141716A) and occurred in CB1(-/-) mice [12].
  • Palmitoleic and oleic acid seem to be especially important for sleep disorders, may be due to their function as precursors of the sleep inducing oleamide [13].
  • Oleamide and oleoylglycine both induced profound hypothermia and decreased locomotion, over equivalent dose ranges and time courses, whereas, closely related compounds, stearamide and oleic acid, were essentially without effect [14].

Biological context of Armoslip CP

  • When administered together, 5-HT and oleamide showed additive or greater than additive effects in reducing body temperature [1].
  • Additionally, our data indicate that oleamide acts at an apparent allosteric site on the 5HT7 receptor and elicits functional responses via activation of this site [15].
  • These results indicate that oleamide can modulate 5HT-mediated signal transduction at different subtypes of mammalian 5HT receptors [15].
  • We used several human osteoblastic cell lines, as well as bone-derived primary osteoblastic cells, to show that confluent cultures of human osteoblastic cells grown under osteogenic conditions developed an adipocytic phenotype after 3 days of complete inhibition of GJC using AGRA or oleamide, two dissimilar nontoxic reversible inhibitors [16].
  • The biosynthesis and tissue distribution of oleamide remain to be assessed in order to both substantiate its role as a sleep-inducing factor and investigate its participation in other physiopathological situations [17].

Anatomical context of Armoslip CP


Associations of Armoslip CP with other chemical compounds


Gene context of Armoslip CP


Analytical, diagnostic and therapeutic context of Armoslip CP


  1. No hypothermic response to serotonin in 5-HT7 receptor knockout mice. Hedlund, P.B., Danielson, P.E., Thomas, E.A., Slanina, K., Carson, M.J., Sutcliffe, J.G. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  2. A derivative of oleamide potently inhibits the spontaneous metastasis of mouse melanoma BL6 cells. Ito, A., Morita, N., Miura, D., Koma, Y., Kataoka, T.R., Yamasaki, H., Kitamura, Y., Kita, Y., Nojima, H. Carcinogenesis (2004) [Pubmed]
  3. Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells. Merkler, D.J., Chew, G.H., Gee, A.J., Merkler, K.A., Sorondo, J.P., Johnson, M.E. Biochemistry (2004) [Pubmed]
  4. Functional role for cannabinoids in respiratory stability during sleep. Carley, D.W., Paviovic, S., Janelidze, M., Radulovacki, M. Sleep. (2002) [Pubmed]
  5. Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide. Boger, D.L., Sato, H., Lerner, A.E., Hedrick, M.P., Fecik, R.A., Miyauchi, H., Wilkie, G.D., Austin, B.J., Patricelli, M.P., Cravatt, B.F. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  6. The endogenous lipid oleamide activates serotonin 5-HT7 neurons in mouse thalamus and hypothalamus. Thomas, E.A., Cravatt, B.F., Sutcliffe, J.G. J. Neurochem. (1999) [Pubmed]
  7. Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats. Huitrón-Reséndiz, S., Gombart, L., Cravatt, B.F., Henriksen, S.J. Exp. Neurol. (2001) [Pubmed]
  8. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Cravatt, B.F., Giang, D.K., Mayfield, S.P., Boger, D.L., Lerner, R.A., Gilula, N.B. Nature (1996) [Pubmed]
  9. Fatty acid amide hydrolase controls mouse intestinal motility in vivo. Capasso, R., Matias, I., Lutz, B., Borrelli, F., Capasso, F., Marsicano, G., Mascolo, N., Petrosino, S., Monory, K., Valenti, M., Di Marzo, V., Izzo, A.A. Gastroenterology (2005) [Pubmed]
  10. Gap junction-mediated cell-cell communication modulates mouse neural crest migration. Huang, G.Y., Cooper, E.S., Waldo, K., Kirby, M.L., Gilula, N.B., Lo, C.W. J. Cell Biol. (1998) [Pubmed]
  11. The sleep-inducing lipid oleamide deconvolutes gap junction communication and calcium wave transmission in glial cells. Guan, X., Cravatt, B.F., Ehring, G.R., Hall, J.E., Boger, D.L., Lerner, R.A., Gilula, N.B. J. Cell Biol. (1997) [Pubmed]
  12. Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo. Lichtman, A.H., Hawkins, E.G., Griffin, G., Cravatt, B.F. J. Pharmacol. Exp. Ther. (2002) [Pubmed]
  13. Fatty acids and sleep in depressed inpatients. Irmisch, G., Schl??fke, D., Gierow, W., Herpertz, S., Richter, J. Prostaglandins Leukot. Essent. Fatty Acids (2007) [Pubmed]
  14. In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide. Chaturvedi, S., Driscoll, W.J., Elliot, B.M., Faraday, M.M., Grunberg, N.E., Mueller, G.P. Prostaglandins Other Lipid Mediat. (2006) [Pubmed]
  15. Unique allosteric regulation of 5-hydroxytryptamine receptor-mediated signal transduction by oleamide. Thomas, E.A., Carson, M.J., Neal, M.J., Sutcliffe, J.G. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  16. Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro. Schiller, P.C., D'Ippolito, G., Brambilla, R., Roos, B.A., Howard, G.A. J. Biol. Chem. (2001) [Pubmed]
  17. The palmitoylethanolamide and oleamide enigmas : are these two fatty acid amides cannabimimetic? Lambert, D.M., Di Marzo, V. Current medicinal chemistry. (1999) [Pubmed]
  18. A catalytic antibody produces fluorescent tracers of gap junction communication in living cells. Subauste, M.C., List, B., Guan, X., Hahn, K.M., Lerner, R., Gilula, N.B. J. Biol. Chem. (2001) [Pubmed]
  19. Structural requirements for 5-HT2A and 5-HT1A serotonin receptor potentiation by the biologically active lipid oleamide. Boger, D.L., Patterson, J.E., Jin, Q. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  20. Clarifying the catalytic roles of conserved residues in the amidase signature family. Patricelli, M.P., Cravatt, B.F. J. Biol. Chem. (2000) [Pubmed]
  21. Connexin 26 expression prevents down-regulation of barrier and fence functions of tight junctions by Na+/K+-ATPase inhibitor ouabain in human airway epithelial cell line Calu-3. Go, M., Kojima, T., Takano, K., Murata, M., Koizumi, J., Kurose, M., Kamekura, R., Osanai, M., Chiba, H., Spray, D.C., Himi, T., Sawada, N. Exp. Cell Res. (2006) [Pubmed]
  22. Enhanced radiosensitization of p53 mutant cells by oleamide. Lee, Y.J., Chung, d.a. .Y., Lee, S.J., Ja Jhon, G., Lee, Y.S. Int. J. Radiat. Oncol. Biol. Phys. (2006) [Pubmed]
  23. Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules. Boger, D.L., Henriksen, S.J., Cravatt, B.F. Curr. Pharm. Des. (1998) [Pubmed]
  24. Fatty acid amide hydrolase, the degradative enzyme for anandamide and oleamide, has selective distribution in neurons within the rat central nervous system. Thomas, E.A., Cravatt, B.F., Danielson, P.E., Gilula, N.B., Sutcliffe, J.G. J. Neurosci. Res. (1997) [Pubmed]
  25. Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems. Fedorova, I., Hashimoto, A., Fecik, R.A., Hedrick, M.P., Hanus, L.O., Boger, D.L., Rice, K.C., Basile, A.S. J. Pharmacol. Exp. Ther. (2001) [Pubmed]
  26. Effect of oleamide on Ca(2+) signaling in human bladder cancer cells. Lo, Y.K., Tang, K.Y., Chang, W.N., Lu, C.H., Cheng, J.S., Lee, K.C., Chou, K.J., Liu, C.P., Chen, W.C., Su, W., Law, Y.P., Jan, C.R. Biochem. Pharmacol. (2001) [Pubmed]
  27. Determination of oleamide and erucamide in polyethylene films by pressurised fluid extraction and gas chromatography. Garrido-López, A., Esquiu, V., Tena, M.T. Journal of chromatography. A. (2006) [Pubmed]
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