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Chemical Compound Review

AG-H-89851     N-(2-hydroxyethyl)icosa- 5,8,11,14...

Synonyms: KBioGR_000253, KBioSS_000253, CBiol_002041, CTK8F7768, KBio2_000253, ...
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Disease relevance of C11695

  • Monocytes from cirrhotic but not control patients or rats elicited SR141716A-sensitive hypotension in normal recipient rats and showed significantly elevated levels of anandamide [1].
  • This inhibitory effect is specific for anandamide as compared to co-released congeners or structural analogues, is sensitive to pertussis toxin and to protein-alkylating agents, and is neither mimicked by cannabinoid-receptor agonists nor prevented by a cannabinoid-receptor antagonist [2].
  • These results implicate anandamide and vascular CB1 receptors in the vasodilated state in advanced cirrhosis and indicate a novel approach for its management [1].
  • Here we show that the endogenous cannabinoid anandamide exerts dual effects on bronchial responsiveness in rodents: it strongly inhibits bronchospasm and cough evoked by the chemical irritant, capsaicin, but causes bronchospasm when the constricting tone exerted by the vagus nerve is removed [3].
  • We conclude that anandamide acting at hepatic CB(1) contributes to diet-induced obesity and that the FAS pathway may be a common molecular target for central appetitive and peripheral metabolic regulation [4].

Psychiatry related information on C11695


High impact information on C11695


Chemical compound and disease context of C11695

  • In the current report, the net uptake of anandamide in cultured neuroblastoma (N18) and glioma (C6) cells, which contain FAAH, was decreased by nearly 50% after 6 min of incubation in the presence of MAFP [11].
  • Recently, we have shown that treatment of rat C6 glioma cells with the raft disruptor methyl-beta-cyclodextrin (MCD) doubles the binding of anandamide (AEA) to type-1 cannabinoid receptors (CB1R), followed by CB1R-dependent signaling via adenylate cyclase and p42/p44 MAPK activity [12].
  • Furthermore, our data show that pharmacological concentrations of celecoxib may interfere with the proapoptotic action of R(+)-MA and anandamide, suggesting that cotreatment with COX-2 inhibitors could diminish glioma regression induced by these compounds [13].
  • Maternal under-nutrition resulted in a striking decrease in body weight of weaning rats, paralleled by a decrease in the hypothalamic levels of the endocannabinoid anandamide, but not of 2-arachidonoylglycerol [14].
  • Palmitoylethanolamide inhibits the expression of fatty acid amide hydrolase and enhances the anti-proliferative effect of anandamide in human breast cancer cells [15].

Biological context of C11695


Anatomical context of C11695

  • Here we show that anandamide is a potent inhibitor of gap-junction conductance and dye permeability in striatal astrocytes [2].
  • These findings indicate that activation of peripheral CB1 cannabinoid receptors contributes to haemorrhagic hypotension, and anandamide produced by macrophages may be a mediator of this effect [20].
  • The potent analgesic effects of cannabis-like drugs and the presence of CB1-type cannabinoid receptors in pain-processing areas of the brain and spinal cord indicate that endogenous cannabinoids such as anandamide may contribute to the control of pain transmission within the central nervous system (CNS) [21].
  • Inhibition by anandamide of gap junctions and intercellular calcium signalling in striatal astrocytes [2].
  • Anandamide inhibited the specific binding of a radiolabeled cannabinoid probe to synaptosomal membranes in a manner typical of competitive ligands and produced a concentration-dependent inhibition of the electrically evoked twitch response to the mouse vas deferens, a characteristic effect of psychotropic cannabinoids [22].

Associations of C11695 with other chemical compounds


Gene context of C11695

  • Acute leptin treatment of normal rats and ob/ob mice reduces anandamide and 2-arachidonoyl glycerol in the hypothalamus [10].
  • Here we provide evidence that a critical balance between anandamide synthesis by N-acylphosphatidylethanolamine-selective phospholipase D (NAPE-PLD) and its degradation by fatty acid amide hydrolase (FAAH) in mouse embryos and oviducts creates locally an appropriate "anandamide tone" for normal development of embryos and their oviductal transport [25].
  • The endocannabinoid anandamide protects neurons during CNS inflammation by induction of MKP-1 in microglial cells [26].
  • RESULTS: All tissues and cells analyzed contain anandamide, 2-AG, CBRs, and FAAH [18].
  • As yet, endogenously produced anandamide has not been shown to activate TRPV1, but this is of importance to understand the physiological function of this interaction [24].

Analytical, diagnostic and therapeutic context of C11695

  • Gas-chromatography/mass-spectrometry measurements indicate that the levels of anandamide and PEA in the skin are enough to cause a tonic activation of local cannabinoid receptors [21].
  • In a further study, we measured anandamide hydrolase concentration in 120 women who were 7-8 weeks pregnant and compared these findings with subsequent pregnancy outcome [19].
  • RESULTS: Oral administration of CT to mice resulted in an increase in fluid accumulation in the small intestine and in increased levels of the endogenous cannabinoid, anandamide, and increased expression of the cannabinoid CB(1) receptor mRNA [27].
  • Electrical stimulation of the dorsal and lateral PAG produced CB1 cannabinoid receptor-mediated analgesia accompanied by a marked increase in the release of anandamide in the PAG, suggesting that endogenous anandamide mediates the behavioral analgesia [28].
  • Here, the development of a sensitive method for measuring cannabinoids by atmospheric pressure-chemical ionization mass spectrometry permitted measurement of the release of the endogenous cannabinoid anandamide in the periaqueductal gray (PAG) by in vivo microdialysis in the rat [28].


  1. Endocannabinoids acting at vascular CB1 receptors mediate the vasodilated state in advanced liver cirrhosis. Bátkai, S., Járai, Z., Wagner, J.A., Goparaju, S.K., Varga, K., Liu, J., Wang, L., Mirshahi, F., Khanolkar, A.D., Makriyannis, A., Urbaschek, R., Garcia, N., Sanyal, A.J., Kunos, G. Nat. Med. (2001) [Pubmed]
  2. Inhibition by anandamide of gap junctions and intercellular calcium signalling in striatal astrocytes. Venance, L., Piomelli, D., Glowinski, J., Giaume, C. Nature (1995) [Pubmed]
  3. Bidirectional control of airway responsiveness by endogenous cannabinoids. Calignano, A., Kátona, I., Désarnaud, F., Giuffrida, A., La Rana, G., Mackie, K., Freund, T.F., Piomelli, D. Nature (2000) [Pubmed]
  4. Endocannabinoid activation at hepatic CB1 receptors stimulates fatty acid synthesis and contributes to diet-induced obesity. Osei-Hyiaman, D., DePetrillo, M., Pacher, P., Liu, J., Radaeva, S., Bátkai, S., Harvey-White, J., Mackie, K., Offertáler, L., Wang, L., Kunos, G. J. Clin. Invest. (2005) [Pubmed]
  5. Prenatal elevation of endocannabinoids corrects the unbalance between dopamine systems and reduces activity in the Naples High Excitability rats. Viggiano, D., Ruocco, L.A., Pignatelli, M., Grammatikopoulos, G., Sadile, A.G. Neuroscience and biobehavioral reviews. (2003) [Pubmed]
  6. Cerebrospinal anandamide levels are elevated in acute schizophrenia and are inversely correlated with psychotic symptoms. Giuffrida, A., Leweke, F.M., Gerth, C.W., Schreiber, D., Koethe, D., Faulhaber, J., Klosterkötter, J., Piomelli, D. Neuropsychopharmacology (2004) [Pubmed]
  7. Blood levels of the endocannabinoid anandamide are increased in anorexia nervosa and in binge-eating disorder, but not in bulimia nervosa. Monteleone, P., Matias, I., Martiadis, V., De Petrocellis, L., Maj, M., Di Marzo, V. Neuropsychopharmacology (2005) [Pubmed]
  8. Structure and function of fatty acid amide hydrolase. McKinney, M.K., Cravatt, B.F. Annu. Rev. Biochem. (2005) [Pubmed]
  9. Modulation of anxiety through blockade of anandamide hydrolysis. Kathuria, S., Gaetani, S., Fegley, D., Valiño, F., Duranti, A., Tontini, A., Mor, M., Tarzia, G., La Rana, G., Calignano, A., Giustino, A., Tattoli, M., Palmery, M., Cuomo, V., Piomelli, D. Nat. Med. (2003) [Pubmed]
  10. Leptin-regulated endocannabinoids are involved in maintaining food intake. Di Marzo, V., Goparaju, S.K., Wang, L., Liu, J., Bátkai, S., Járai, Z., Fezza, F., Miura, G.I., Palmiter, R.D., Sugiura, T., Kunos, G. Nature (2001) [Pubmed]
  11. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. Deutsch, D.G., Glaser, S.T., Howell, J.M., Kunz, J.S., Puffenbarger, R.A., Hillard, C.J., Abumrad, N. J. Biol. Chem. (2001) [Pubmed]
  12. Effect of lipid rafts on cb2 receptor signaling and 2-arachidonoyl-glycerol metabolism in human immune cells. Bari, M., Spagnuolo, P., Fezza, F., Oddi, S., Pasquariello, N., Finazzi-Agr??, A., Maccarrone, M. J. Immunol. (2006) [Pubmed]
  13. Up-regulation of cyclooxygenase-2 expression is involved in R(+)-methanandamide-induced apoptotic death of human neuroglioma cells. Hinz, B., Ramer, R., Eichele, K., Weinzierl, U., Brune, K. Mol. Pharmacol. (2004) [Pubmed]
  14. Effect of maternal under-nutrition on pup body weight and hypothalamic endocannabinoid levels. Matias, I., Léonhardt, M., Lesage, J., De Petrocellis, L., Dupouy, J.P., Vieau, D., Di Marzo, V. Cell. Mol. Life Sci. (2003) [Pubmed]
  15. Palmitoylethanolamide inhibits the expression of fatty acid amide hydrolase and enhances the anti-proliferative effect of anandamide in human breast cancer cells. Di Marzo, V., Melck, D., Orlando, P., Bisogno, T., Zagoory, O., Bifulco, M., Vogel, Z., De Petrocellis, L. Biochem. J. (2001) [Pubmed]
  16. An anorexic lipid mediator regulated by feeding. Rodríguez de Fonseca, F., Navarro, M., Gómez, R., Escuredo, L., Nava, F., Fu, J., Murillo-Rodríguez, E., Giuffrida, A., LoVerme, J., Gaetani, S., Kathuria, S., Gall, C., Piomelli, D. Nature (2001) [Pubmed]
  17. Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Zygmunt, P.M., Petersson, J., Andersson, D.A., Chuang, H., Sørgård, M., Di Marzo, V., Julius, D., Högestätt, E.D. Nature (1999) [Pubmed]
  18. Possible endocannabinoid control of colorectal cancer growth. Ligresti, A., Bisogno, T., Matias, I., De Petrocellis, L., Cascio, M.G., Cosenza, V., D'argenio, G., Scaglione, G., Bifulco, M., Sorrentini, I., Di Marzo, V. Gastroenterology (2003) [Pubmed]
  19. Relation between decreased anandamide hydrolase concentrations in human lymphocytes and miscarriage. Maccarrone, M., Valensise, H., Bari, M., Lazzarin, N., Romanini, C., Finazzi-Agrò, A. Lancet (2000) [Pubmed]
  20. Activation of peripheral CB1 cannabinoid receptors in haemorrhagic shock. Wagner, J.A., Varga, K., Ellis, E.F., Rzigalinski, B.A., Martin, B.R., Kunos, G. Nature (1997) [Pubmed]
  21. Control of pain initiation by endogenous cannabinoids. Calignano, A., La Rana, G., Giuffrida, A., Piomelli, D. Nature (1998) [Pubmed]
  22. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Devane, W.A., Hanus, L., Breuer, A., Pertwee, R.G., Stevenson, L.A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., Mechoulam, R. Science (1992) [Pubmed]
  23. Endogenous cannabinoids mediate retrograde signalling at hippocampal synapses. Wilson, R.I., Nicoll, R.A. Nature (2001) [Pubmed]
  24. Anandamide acts as an intracellular messenger amplifying Ca2+ influx via TRPV1 channels. van der Stelt, M., Trevisani, M., Vellani, V., De Petrocellis, L., Schiano Moriello, A., Campi, B., McNaughton, P., Geppetti, P., Di Marzo, V. EMBO J. (2005) [Pubmed]
  25. Fatty acid amide hydrolase deficiency limits early pregnancy events. Wang, H., Xie, H., Guo, Y., Zhang, H., Takahashi, T., Kingsley, P.J., Marnett, L.J., Das, S.K., Cravatt, B.F., Dey, S.K. J. Clin. Invest. (2006) [Pubmed]
  26. The endocannabinoid anandamide protects neurons during CNS inflammation by induction of MKP-1 in microglial cells. Eljaschewitsch, E., Witting, A., Mawrin, C., Lee, T., Schmidt, P.M., Wolf, S., Hoertnagl, H., Raine, C.S., Schneider-Stock, R., Nitsch, R., Ullrich, O. Neuron (2006) [Pubmed]
  27. An endogenous cannabinoid tone attenuates cholera toxin-induced fluid accumulation in mice. Izzo, A.A., Capasso, F., Costagliola, A., Bisogno, T., Marsicano, G., Ligresti, A., Matias, I., Capasso, R., Pinto, L., Borrelli, F., Cecio, A., Lutz, B., Mascolo, N., Di Marzo, V. Gastroenterology (2003) [Pubmed]
  28. Pain modulation by release of the endogenous cannabinoid anandamide. Walker, J.M., Huang, S.M., Strangman, N.M., Tsou, K., Sañudo-Peña, M.C. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
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