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Chemical Compound Review

Anandamide     (5Z,8Z,11Z,14Z)-N-(2- hydroxyethyl)icosa-5...

Synonyms: AnNH, AC1NQZCS, CHEMBL15848, CPD-7598, CHEBI:2700, ...
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Disease relevance of AEA


High impact information on AEA


Biological context of AEA


Anatomical context of AEA

  • In the present study, we analyzed the effect of arachidonyl ethanolamide (AEA) on cervical carcinoma (CxCa) cell lines [7].
  • Isolated human atrial heart muscle preparations were stimulated by electrical field with 1 Hz to contract isometrically at optimal length and were challenged with the endogenous cannabinoid arachidonyl ethanolamide (anandamide), the metabolically stable analogue R-methanandamide, and the potent synthetic CB(1) receptor agonist HU-210 [9].

Associations of AEA with other chemical compounds


Gene context of AEA


  1. Mesenteric vasodilation mediated by endothelial anandamide receptors. Wagner, J.A., Varga, K., Járai, Z., Kunos, G. Hypertension (1999) [Pubmed]
  2. Inhibitors of arachidonoyl ethanolamide hydrolysis. Koutek, B., Prestwich, G.D., Howlett, A.C., Chin, S.A., Salehani, D., Akhavan, N., Deutsch, D.G. J. Biol. Chem. (1994) [Pubmed]
  3. Mice lacking fatty acid amide hydrolase exhibit a cannabinoid receptor-mediated phenotypic hypoalgesia. Lichtman, A.H., Shelton, C.C., Advani, T., Cravatt, B.F. Pain (2004) [Pubmed]
  4. Respiratory actions of vanilloid receptor agonists in the nucleus of the solitary tract: comparison of resiniferatoxin with non-pungent agents and anandamide. Geraghty, D.P., Mazzone, S.B. Br. J. Pharmacol. (2002) [Pubmed]
  5. Human mast cells take up and hydrolyze anandamide under the control of 5-lipoxygenase and do not express cannabinoid receptors. Maccarrone, M., Fiorucci, L., Erba, F., Bari, M., Finazzi-Agrò, A., Ascoli, F. FEBS Lett. (2000) [Pubmed]
  6. Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors. Wagner, J.A., Járai, Z., Bátkai, S., Kunos, G. Eur. J. Pharmacol. (2001) [Pubmed]
  7. Arachidonyl ethanolamide induces apoptosis of uterine cervix cancer cells via aberrantly expressed vanilloid receptor-1. Contassot, E., Tenan, M., Schnüriger, V., Pelte, M.F., Dietrich, P.Y. Gynecol. Oncol. (2004) [Pubmed]
  8. Effect of the CB1 receptor antagonist, SR141716A, on cannabinoid-induced ocular hypotension in normotensive rabbits. Pate, D.W., Järvinen, K., Urtti, A., Mahadevan, V., Järvinen, T. Life Sci. (1998) [Pubmed]
  9. Cannabinoids acting on CB1 receptors decrease contractile performance in human atrial muscle. Bonz, A., Laser, M., Küllmer, S., Kniesch, S., Babin-Ebell, J., Popp, V., Ertl, G., Wagner, J.A. J. Cardiovasc. Pharmacol. (2003) [Pubmed]
  10. A fluorescence displacement assay for the measurement of arachidonoyl ethanolamide (anandamide) and oleoyl amide (octadecenoamide) hydrolysis. Thumser, A.E., Voysey, J., Wilton, D.C. Biochem. Pharmacol. (1997) [Pubmed]
  11. Potential biosynthetic connections between the two cannabimimetic eicosanoids, anandamide and 2-arachidonoyl-glycerol, in mouse neuroblastoma cells. Di Marzo, V., De Petrocellis, L., Sugiura, T., Waku, K. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  12. Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase. Bisogno, T., Melck, D., De Petrocellis, L., Bobrov MYu, n.u.l.l., Gretskaya, N.M., Bezuglov, V.V., Sitachitta, N., Gerwick, W.H., Di Marzo, V. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  13. Integrin clustering enables anandamide-induced Ca2+ signaling in endothelial cells via GPR55 by protection against CB1-receptor-triggered repression. Waldeck-Weiermair, M., Zoratti, C., Osibow, K., Balenga, N., Goessnitzer, E., Waldhoer, M., Malli, R., Graier, W.F. J. Cell. Sci. (2008) [Pubmed]
  14. N-acylphosphatidylethanolamine-hydrolysing phospholipase D lacks the ability to transphosphatidylate. Petersen, G., Hansen, H.S. FEBS Lett. (1999) [Pubmed]
  15. Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor. Deutsch, D.G., Lin, S., Hill, W.A., Morse, K.L., Salehani, D., Arreaza, G., Omeir, R.L., Makriyannis, A. Biochem. Biophys. Res. Commun. (1997) [Pubmed]
  16. A structure-activity relationship study on N-arachidonoyl-amino acids as possible endogenous inhibitors of fatty acid amide hydrolase. Grazia Cascio, M., Minassi, A., Ligresti, A., Appendino, G., Burstein, S., Di Marzo, V. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  17. Anandamide biosynthesis catalyzed by the phosphodiesterase GDE1 and detection of glycerophospho-N-acyl ethanolamine precursors in mouse brain. Simon, G.M., Cravatt, B.F. J. Biol. Chem. (2008) [Pubmed]
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