Biochemistry and pharmacology of arachidonylethanolamide, a putative endogenous cannabinoid

Journal of Lipid Research

Volumn 38, Issue 12, 1997, Pages 2383-2398

  Hillard, Cecilia J ^a   Campbell, William B ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

9 tetrahydrocannabinol; Amidohydrolase; Fatty acyl amide hydrolase; Marijuana; N acylethanolamines

Indexed keywords

2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ACYLTRANSFERASE; AMIDASE; ANANDAMIDE; ARACHIDONIC ACID; CALCIUM ION; CANNABINOID; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; CANNABIS; DEXANABINOL; DRONABINOL; PHOSPHODIESTERASE; PHOSPHOLIPASE D; RIMONABANT;

ANIMAL TISSUE; ARTICLE; ASTROCYTE; BRAIN FUNCTION; CALCIUM CELL LEVEL; CANNABIS ADDICTION; CELL MEMBRANE TRANSPORT; DRUG MECHANISM; ENZYME ACTIVITY; GAP JUNCTION; HUMAN; HUMAN TISSUE; NERVE CELL; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ACTIVITY RELATION; SWINE;

ACYLTRANSFERASES; ANIMALS; ARACHIDONIC ACIDS; BIOLOGICAL TRANSPORT; BRAIN; CANNABINOIDS; HYDROLYSIS; HYDROXYLATION; PHOSPHATIDYLETHANOLAMINES; POLYUNSATURATED ALKAMIDES; PROTEIN BINDING; RECEPTORS, CANNABINOID; RECEPTORS, DRUG;

EID: 0031443586     PISSN: 00222275     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (118)

1. Devane, W. A., L. Hanus, A. Breuer, R. G. Pertwee, L. A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, and R. Mechoulam. 1992. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 258: 1946-1949.
2. Bachur, N. R., K. Masek, K. L. Melmon, and S. Udenfriend. 1965. Fatty acid amides of ethanolamine in mammalian tissues. J. Biol. Chem. 240: 1019-1024.
3. Epps, D. E., P. C. Schmid, V. Natarajan, and H. H. O. Schmid. 1979. N-Acylethanolamine accumulation in infarcted myocardium. Biochem. Biophys. Res. Commun. 90: 628-633.
4. Schmid, H. H. O., P. C. Schmid, and V. Naiarajan. 1990. N-Acylated glycerophospholipids and their derivatives. Prog. Lipid Res. 29: 1-43.
5. Schmid, P. C., R. J. Krebsbach, S. R. Perry, T. M. Dettmer, J. L. Maasson, and H. H. O. Schmid. 1995. Occurrence and postmortem generation of anandamide and other long chain N-acylethanolamines in mammalian brain. FEBS Lett. 375: 117-120.
6. Schmid, P. C., R. J. Krebsbach, S. R. Perry, T. M. Dettmer, J. L. Maasson, and H. H. O. Schmid. 1996. Corrigendum to: Occurrence and postmortem generation of anandamide and other long chain N-acylethanolamines in mammalian brain. FEBS Lett. 382: 125-126.
7. Felder, C. C., A. Nielsen, E. M. Briley, M. Palkovits, J. Priller, J. Axelrod, D. N. Nguyen, J. M. Richardson, R. M. Riggin, G. A. Koppel, S. M. Paul, and G. W. Becker. 1996. Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 393: 231-235.
8. Kempe, K., F-F. Hsu, A. Bohrer, and J. Turk. 1996. Isotope dilution mass spectrometric measurements indicate that arachidonylethanolamide, the proposed endogenous ligand of the cannabinoid receptor, accumulates in rat brain tissue postmortem. J. Biol. Chem. 271: 17287-17295.
9. Koga, D., T. Santa, K. Hagiwara, K. Imai, H. Takizawa, T. Nagano, M. Hirobe, M. Ogawa, T. Sato, and K. Inoue. 1995. High-performance liquid chromatography and fluorometric detection of arachidonylethanolamide (anandamide) and its analogues, derivatized with 4-(N-chloroformylmethyl-N-methyl)amino-7-N,N-dimethylaminosulphonyl-2,1,3- benzoxadiazole (DBD-COCl). Biomed. Chromatogr. 9: 56-57.
10. Sugiura, T., S. Kondo, A. Sukagawa, T. Tonegawa, S. Nakane, A. Yamashita, Y. Ishima, and K. Waku. 1996. Transacylase-mediated and phosphodiesterase-mediated synthesis of N-arachidonylethanolamine, an endogenous cannabinoid-receptor ligand, in rat brain microsomes. Eur. J. Biochem. 240: 53-62.
11. DiMarzo, V., X. Fontana, H. Cadas, S. Schinelli, G. Cimino, J-C. Schwartz, and D. Piomelli. 1994. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature. 372: 686-691.
12. DiMarzo, V., L. De Petrocellis, N. Sepe, and A. Buono. 1996. Biosynthesis of anandamide and related acylethanolamides in mouse J774 macrophages and N18 neuroblastoma cells. Biochem. J. 316: 977-984.
13. Randall, M. D., S. P. H. Alexander, T. Bennett, E. A. Boyd, J. R. Fry, S. M. Gardiner, P. A. Kemp, A. I. McCulloch, and D. A. Kendall. 1996. An endogenous cannabinoid as an endothelium-derived vasorelaxant. Biochem. Biophys. Res. Commun. 229: 114-120.
14. 9-tetrahydrocannabinol (THC). Biochem. Pharmacol. 49: 855-858.
15. Schmid, H. H. O., P. C. Schmid, and V. Natarajan. 1996. The N-acylation-phosphodiesterase pathway and cell signaling. Chem. Phys. Lipids. 80: 133-142.
16. 2+-dependent transacylase and phosphodiesterase activities. Biochem. Biophys. Res. Commun. 218: 113-117.
17. Blank, M. L., E. A. Cress, M. Robinson, and F. Snyder. 1985. Metabolism of unique diarachidonoyl and linoleoylarachidonoyl species of ethanolamine and choline phosphoglycerides in rat testes. Biochim. Biophys. Acta. 833: 366-371.
18. Natarajan, V., P. C. Schmid, P. V. Reddy, and H. H. O. Schmid. 1984. Catabolism of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 42: 1613-1619.
19. Natarajan, V., P. C. Schmid, P. V. Reddy, M. L. Zuzarte-Augustin, and H. H. O. Schmid. 1983. Biosynthesis of N-acylethanolamine phospholipids by dog brain preparations. J. Neurochem. 41: 1303-1312.
20. Cadas, H., S. Gaillet, M. Beltramo, L. Venance, and D. Piomelli. 1996. Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP. J. Neurosci. 16: 3934-3942.
21. Hansen, H. S., L. Lauritzen, A. M. Strand, B. Moesgaard, and A. Frandsen. 1995. Glutamate stimulates the formation of N-acylphosphatidylethanolamine and N-acylethanolamine in cortical neurons in culture. Biochim. Biophys. Acta. 1258: 303-308.
22. Natarajan, V., P. V. Reddy, P. C. Schmid, and H. H. O. Schmid. 1982. N-Acylation of ethanolamine phospholipids in canine myocardium. Biochim. Biophys. Acta. 712: 342-355.
23. Reddy, P. V., V. Natarajan, P. C. Schmid, and H. H. O. Schmid. 1983. N-Acylation of dog heart ethanolamine phospholipids by transacylase activity. Biochim. Biophys. Acta. 750: 472-480.
24. Reddy, P. V., P. C. Schmid, V. Natarajan, and H. H. O. Schmid. 1983. The role of cardiolipin as an acyl donor in clog heart N-acylethanolamine phospholipid biosynthesis. Biochim. Biophys. Acta. 751: 241-246.
25. Nakanishi, S. 1992. Molecular diversity of glutamate receptors and implications lor brain function. Science. 258: 597-603.
26. Colodzin, M., N. R. Bachur, H. Weissbach, and S. Udenfriend. 1963. Enzymatic formation of laity acid amides. Biochem. Biophys. Res. Commun. 10: 165-170.
27. Bachur, N. R., and S. Udenfriend. 1965. Microsomal synthesis of fatty acid amides. J. Biol. Chem. 241: 1308-1313.
28. Deutsch, D. G., and S. A. Chin. 1993. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem. Pharmacol. 46: 791-796.
29. Kruszka, K. K., and R. W. Gross. 1994. The ATP- and CoA-independent synthesis of arachidonylethanolamide. J. Biol. Chem. 269: 14345-14348.
30. Devane, W. A., and J. Axelrod. 1994. Enzymatic synthesis of anandamide, an endogenous ligand for the cannabinoid receptor, by brain membranes. Proc. Natl. Acad. Sci. USA. 91: 6698-6701.
31. Schmid, P. C., M. L. Zuzarte-Augustin, and H. H. O. Schmid. 1985. Properties of rat liver N-acylethanolamine amidohydrolase. J. Biol. Chem. 260: 14145-14149.
32. Ueda, N., Y. Kurahashi, S. Yamamoto, and T. Tokunaga. 1995. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J. Biol. Chem. 270: 23823-23827.
33. Desarnaud, F., H. Cadas, and D. Piomelli. 1995. Anandamide amidohydrolase activity in rat brain microsomes. J. Biol. Chem. 270: 6030-6035.
34. Hillard, C. J., D. M. Wilkison, W. S. Edgemond, and W. B. Campbell. 1995. Characterization of the kinetics and distribution of N-arachidonylethanolamine (anandamide) hydrolysis by rat brain. Biochim. Biophys. Acta. 1257: 249-256.
35. Pertwee, R. G., S. R. Fernando, G. Griffin, V. Abadji, and A. Makriyannis. 1995. Effect of phenylmethylsulphonyl fluoride on the potency of anandamide as an inhibitor of electrically evoked contractions in two isolated tissue preparations. Eur. J. Pharmacol. 272: 73-78.
36. Hillard, C. J., W. S. Edgemond, A. Jarrahian, and W. B. Campbell. 1997. Accumulation of N-arachidonylethanolamine (anandamide) into cerebellar granule cells occurs via facilitated diffusion. J. Neurochem. 69: 631-638.
37. Cravatt, B. F., O. Prospero-Garcia, G. Siuzdak, N. B. Gilul, S. J. Henriksen, D. L. Bolger, and R. A. Lerner. 1995. Chemical characterization of a family of brain lipids that induce sleep. Science. 268: 1506-1509.
38. Maurelli, S., T. Bisogno, L. DePetrocellis, A. DiLuccia, G. Marino, and V. DiMarzo. 1995. Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma "anandamide amidohydrolase." FEBS Lett. 377: 82-86.
39. Cravatt, B. F., D. K. Giang, S. P. Mayfield, D. L. Boger, R. A. Lerner, and N. B. Guila. 1996. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature. 384: 84-87.
40. Lang, W., C. Qin, W. A. G. Hill, S. Lin, A. D. Khanolkar, and A. Makriyannis. 1996. High-performance liquid Chromatographie determination of anandamide amidase activity in rat brain microsomes. Anal. Biochem. 238: 40-45.
41. Koutek, B., G. D. Prestwich, A. C. Howlett, S. A. Chin, D. Salehani, N. Akhavan, and D. G. Deutsch. 1994. Inhibitors of arachidonoyl ethanolamide hydrolysis. J. Biol. Chem. 37: 22937-22940.
42. Krupka, R. M., and R. Deves. 1981. An experimental test for cyclic versus linear transport models. J. Biol. Chem. 256: 5410-5419.
43. Ueda, N., K. Yamamoto, S. Yamamoto, T. Tokunaga, E. Shirakawa, H. Shinkai, M. Ogawa, T. Sato, I. Kudo, K. Inoue, H. Takizawa, T. Nagano, M. Hirobe, N. Matsuki, and H. Saito. 1995. Lipoxygenase-catalyzed oxygenation of arachidonylethanolamide, a cannabinoid receptor agonist. Biochim. Biophys. Acta. 1254: 127-134.
44. Hampson, A. J., W. A. G. Hill, M. Zan-Phillips, A. Makriyannis, E. Leung, R. M. Eglen, and L. M. Bornheim. 1995. Anandamide hydroxylation by brain lipoxygenase: metabolite structures and potencies at the cannabinoid receptor. Biochim. Biophys. Acta. 1259: 173-179.
45. Bornheim, L. M., K. Y. Kim, B. Chen, and M. A. Correia. 1993. The effect of cannabinol on mouse hepatic inicrosomal cytochrome P450-dependent anandamide metabolism. Biochem. Biophys. Res. Commun. 197: 740-746.
46. Bouaboula, M., M. Rinaldi, R. Carayon, C. Carillon, B. Delpech, D. Shire, G. Le Fur, and P. Casellas. 1993. Cannabinoid-receptor expression in human leukocytes. Eur. J. Biochem. 214: 173-180.
47. Bornheim, L. M., K. Y. Kim, B. Chen, and M. A. Correia. 1995. Microsomal cytochrome P450-mediated liver and brain anandamide metabolism. Biochem. Pharmacol. 50: 677-686.
48. Vogel, Z., J. Barg, R. Levy, D. Saya, E. Heldman, and R. Mechoulam. 1993. Anandamide, a brain endogenous compound, interacts specifically with cannabinoid receptors and inhibits adenylate cyclase. J. Neurochem. 61: 352-355.
49. Childers, S. R., T. Sexton, and M. B. Roy. 1994. Effects of anandamide on cannabinoid receptors in rat brain membranes. Biochem. Pharmacol. 47: 711-715.
50. Pinto, J. C., F. Potie, K. C. Rice, D. Boring, M. R. Jonson, D. M. Evans, G. H. Wilken, C. H. Cantrell, and A. C. Howlett. 1994. Cannabinoid receptor binding and agonist activity of amides and esters of arachidonic acid. Mol. Pharmacol. 46: 516-522.
51. Adams, I. B., W. Ryan, M. Singer, B. F. Thomas, D. R. Compton, R. K. Razdan, and B. R. Martin. 1995. Evaluation of cannabinoid receptor binding and in vivo activities for anandamide analogs. J. Pharmacol. Exp. Ther. 273: 1172-1181.
52. Hillard, C. J., W. S. Edgemond, and W. B. Campbell. 1995. Characterization of ligand binding to the cannabinoid receptor of rat brain membranes using a novel method: application to anandamide. J. Neurochem. 64: 677-683.
53. Felder, C. C., E. M. Briley, J. Axelrod, J. T. Simpson, K. Mackie, and W. A. Devane. 1993. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc. Natl. Acad. Sci. USA. 90: 7656-7660.
54. Priller, J., E. M. Briley, J. Mansouri, W. A. Devane, K. Mackie, and C. C. Felder. 1995. Mead ethanolamide, a novel eicosanoid, is an agonist for the central (CB1) and peripheral (CB2) cannabinoid receptors. Mol. Pharmacol. 48: 288-292.
55. Harms, L., A. Gopher, S. Almog, and R. Mechoulam. 1993. Two new unsaturated fatty acid ethanolamides that bind to the cannabinoid receptor. J. Med. Chem. 36: 3032-3034.
56. Wise, M. L., K. Soderstrom, T. F. Murray, and W. H. Gerwick. 1996. Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide, a novel eicosanoid. Experientia. 52: 88-92.
57. Boring, D. L., B. A. Berglund, and A. C. Howlett. 1996. Cerebrodiene, arachidonyl ethanolamide and hybrid structures: potential for interaction with brain cannabinoid receptors. Prostaglandins Leukot. Essent. Fatty Acids. 55: 207-210.
58. Sugiura, T., S. Kondo, A. Sukagawa, S. Nakane, A. Shinoda, K. Itoh, A. Yamashita, and K. Waku. 1995. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 215: 89-92.
59. Abadji, V., S. Lin, G. Taha, G. Griffin, L. A. Stevenson, R. G. Pertwee, and A. Makriyannis. 1994. (R)-Methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability. J. Med. Chem. 37: 1889-1893.
60. Khanolkar, A. D., V. Abadji, S. Ein, W. A. G. Hill, G. Taha, K. Abouzid, Z. Meng, P. Fan, and A. Makriyannis. 1996. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J. Med. Chem. 39: 4515-4519.
61. Adams, I. B., W. Ryan, M. Singer, R. K. Razdan, D. R. Compton, and B. R. Martin. 1995. Pharmacological and behavioral evaluation of alkylated anandamide analogs. Life Sci. 56: 2041-2048.
62. Edgemond, W. S., W. B. Campbell, and C. J. Hillard. 1995. The binding of novel phenolic derivatives of anandamide to brain cannabinoid receptors. Prostaglandins Leukot. Essent. Fatty Acids. 52: 84-86.
63. Mechoulam, R., S. Ben-Shabat, E. Hanus, M. Ligumsky, N. E. Kaminski, A. R. Schatz, A. Gopher, S. Almog, B. R. Martin, D. R. Compton, R. G. Pertwee, G. Griffin, M. Bayewitch, J. Barg, and Z. Vogel. 1995. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem. Pharmacol. 50: 84-90.
64. Munro, S., K. L. Thomas, and M. Abu-Shaar. 1993. Molecular characterization of a peripheral receptor for cannabinoids. Nature. 365: 61-65.
65. Galiegue, S., S. Mary, J. Marchand, D. Dussossoy, D. Carriere, P. Carayon, M. Bouaboula, D. Shire, G. Le Fur, and P. Casellas. 1995. Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur. J. Biochem. 232: 54-61.
66. Felder, C. C., K. E. Joyce, E. M. Briley, J. Mansouri, K. Mackie, O. Blond, Y. Lai, A. L. Ma, and R. L. Mitchell. 1995. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol. Pharmacol. 48: 443-450.
67. Facci, L., R. Dal Toso, S. Romanello, A. Buriani, S. D. Skaper, and A. Leon. 1995. Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc. Natl. Acad. Sci. USA. 92: 3376-3380.
68. Slipetz, D. M., G. P. O'Neill, L. Favreau, C. Dufresne, M. Gallant, Y. Gareau, D. Guay, M. LaBelle, and K. M. Metters. 1995. Activation of the human peripheral cannabinoid receptor results in inhibition of adenylyl cyclase. Mol. Pharmacol. 48: 352-362.
69. Bayewitch, M., T. Avidor-Reiss, R. Levy, J. Barg, R. Mechoulam, and Z. Vogel. 1995. The peripheral cannabinoid receptor adenylate cyclase inhibition and G protein coupling. FEBS Lett. 375: 143-147.
70. Showalter, V. M., D. R. Compton, B. R. Martin, and M. E. Abood. 1996. Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J. Pharmacol. Exp. Ther. 278: 989-999.
71. Devane, W. A., F. A. Dysarz, M. R. Johnson, L. S. Melvin, and A. C. Howlett. 1988. Determination and characterization of a cannabinoid receptor in rat brain. Mol. Pharmacol. 31: 606-613.
72. Houston, D. B., and A. C. Howlett. 1993. Solubilization of the cannabinoid receptor from rat brain and its functional interaction with guanine nucleotide-binding proteins. Mol. Pharmacol, 43: 17-22.
73. 35S] thio]-triphosphate binding. Proc. Natl. Acad. Sci. USA. 92: 7242-7246.
74. Pacheco, M. A., S. J. Ward, and S. R. Childers. 1993. Identification of cannabinoid receptors in cultures of rat cerebellar granule cells. Brain Res. 603: 102-110.
75. Matsuda, L. A., S. J. Lolait, M. J. Brownstein, A. C. Young, and T. I. Bonner. 1990. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature. 346: 561-564.
76. Howlett, A. C. 1985. Cannabinoid inhibition of adenylate cyclase. Biochemistry of the response in neuroblastoma cell membranes. Mol. Pharmacol. 27: 429-436.
77. Felder, C. C., J. S. Veluz, H. L. Williams, E. M. Briley, and L. A. Matsuda. 1992. Cannabinoid agonists stimulate both receptor and non-receptor-mediated signal transduction pathways in cells transfected with and expressing cannabinoid receptor clones. Mol. Pharmacol. 42: 838-845.
78. Caulfield, M. P., and D. A. Brown. 1992. Cannabinoid receptor agonists inhibit Ca current in NG108-15 neuroblastoma cells via a pertussis toxin-sensitive mechanism. Br J. Pharmacol. 106: 231-232.
79. Mackie, K., and B. Hille. 1992. Cannabinoids inhibit N-type calcium channels in neuroblastoma-glioma cells. Proc. Natl. Acad. Sci. USA. 89: 3825-3829.
80. Deadwyler, S. A., R. E. Hampson, J. Mu, A. Whyte, and S. Childers. 1995. Cannabinoids modulate voltage sensitive potassium A-current in hippocampal neurons via a cAMP-dependent process. J. Pharmacol. Exp. Ther. 273: 734-743.
81. Henry, D. J., and C. Chavkin. 1995. Activation of inwardly rectifying potassium channels (GIRK1) by co-expressed rat brain cannabinoid receptors in Xenopus oocytes. Neurosci. Lett. 186: 91-94.
82. Howlett, A. C., J. M. Qualy, and L. L. Khachatrian. 1986. Involvement of Gi in the inhibition of adenylate cyclase by cannabimimetic drugs. Mol. Pharmacol. 29: 307-313.
83. Mackie, K., W. A. Devane, and B. Hille. 1993. Anandamide, an endogenous cannabinoid, inhibits calcium currents as a partial agonist in N18 neuroblastoma cells. Mol. Pharmacol. 44: 498-503.
84. 2+ currents in cat cerebral arterial smooth muscle cells. FASEB J. 10: A302.
85. Pertwee, R. G. 1972. The ring test: a quantitative method lor assessing the cataleptic effect of cannabis in mice. Br. J. Pharmacol. 46: 753-763.
86. Martin, B. R., D. R. Compton, B. F. Thomas, W. R. Prescott, P. J. Little, R. K. Razdan, M. R. Johnson, L. S. Melvin, R. Mechoulam, and S. J. Ward. 1991. Behavioral, biochemical and molecular modeling evaluations of cannabinoid analogs in mice. Pharmacol. Biochem. Behav. 40: 471-478.
87. 9-tetrahydrocannabinol in the rat and mouse. Psychopharmacology. 25: 275-280.
88. 9-tetrahydrocannabinol on brain catecholamine synthesis and plasma corticosterone levels. Psychopharmacology. 67: 215-219.
89. Fride, E., and R. Mechoulam. 1993. Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent. Eur. J. Pharmacol. 231: 313-314.
90. Crawley, J. N., R. L. Corwin, J. K. Robinson, C. C. Felder, W. A. Devane, and J. Axelrod. 1993. Anandamide, an endogenous ligand of the cannabinoid receptor, induces hypomotility and hypothermia in vivo in rats. Pharmacol. Biochem. Behav. 46: 967-972.
91. Smith, P. B., D. R. Compton, S. P. Welch, R. K. Razdan, R. Mechoulam, and B. R. Martin. 1994. The pharmacological activity of anandamide, a putative endogenous cannabinoid, in mice. J. Pharmacol. Exp. Ther. 270: 219-227.
92. Romero, J., E. Garcia-Palermo, S. Y. Lin, J. A. Ramos, A. Makriyannis, and J. J. Fernandex-Ruix. 1996. Extrapyramidal effects of methanandamide, an analog of anandamide the endogenous CB1 receptor ligand. Life Sci. 58: 1249-1257.
93. Welch, S. P., L. D. Dunlow, G. S. Patrick, and R. K. Razdan. 1995. Characterization of anandamide- and fluoroanandamide-induced antinociception and cross-tolerance to delta-9-THC after intrathecal administration to mice: blockade of delta-9-THC-induced analgesia. J. Pharmacol. Exp. Ther. 273: 1235-1244.
94. 9-tetrahydrocannabinol. J. Pharmacol. Exp. Ther. 272: 699-707.
95. Pate, D. W., K. Jarvinen, A. Urti, P. Jarho, and T. Jarvinen. 1995. Ophthalmic arachidonylethanolamide decreases intraocular pressure in normotensive rabbits. Curr. Eye Res. 14: 791-797.
96. Merritt, J. C., S. McKinnon, J. R. Armstrong, G. Hatem, and L. A. Reid. 1980. Oral delta-9-tetrahydrocannabinol in heterogeneous glaucomas. Ann. Ophthalmol. 12: 947-950.
97. Schuel, H., R. Schuel, A. M. Zimmerman, and S. Zimmerman. 1987. Cannabinoids reduce fertility of sea urchin sperm. Biochem. Cell Biol. 65: 130-136.
98. Schuel, H., E. Goldstein, R. Mechoulam, A. M. Zimmerman, and S. Zimmerman. 1994. Anandamide (arachidonylethanolamide), a brain cannabinoid receptor agonist, reduces sperm fertilizing capacity in sea urchins by inhibiting the acrosome reaction. Proc. Natl. Acad. Sci. USA. 91: 7678-7682.
99. Paria, B. C., S. K. Das, and S. K. Dey. 1995. The preimplantation mouse embryo is a target for cannabinoid ligand-receptor signaling. Proc. Natl. Acad. Sci. USA. 92: 9460-9464.
100. Varga, K., K. Lake, B. R. Martin, and G. Kunos. 1995. Novel antagonist implicates the CB1 receptor in the hypotensive action of anandamide. Eur. J. Pharmacol. 278: 279-283.
101. Stein, E. A., S. A. Fuller, W. S. Edgemond, and W. B. Campbell. 1996. Physiological and behavioural effects of the endogenous cannabinoid, arachidonylethanolamide (anandamide), in the rat. Br. J. Pharmacol. 119: 107-114.
102. 9-THC dilation of cerebral arterioles is blocked by indomethacin. Am. J. Physiol. 269: H1859-H1864.
103. Pertwee, R. G., L. A. Stevenson, and G. Griffin. 1993. Cross-tolerance between delta-9-tetrahydrocannabinol and cannabimimetic agents, CP 55,940, Win 55,212-2 and anandamide. Br. J. Pharmacol. 110: 1483-1490.
104. 9-tetrahydrocannabinol. Brain Res. 697: 84-90.
105. Wiley, J., R. Balster, and B. R. Martin. 1995. Discriminative stimulus effects of anandamide in rats. Eur. J. Pharmacol. 276: 49-54.
106. Venance, L., D. Piomelli, J. Glowinski, and C. Glaume. 1995. Inhibition by anandamide of gap junctions and intercellular calcium signalling in striatal astrocytes. Nature 376: 590-594.
107. Nedergaard, M. 1994. Direct signaling from astrocytes to neurons in cultures of mammalian brain cells. Science. 263: 1768-1771.
108. 2+ release from mitochondria by N-acylethanolamines, a class of lipids synthesized in ischemic heart tissue. J. Biol. Chem. 257: 1383-1391.
109. Petronelli, V., A. Nicolli, P. Costantini, R. Colonna, and P. Bernardi. 1994. Regulation of the permeability transition pore, a voltage-dependent mitochondrial channel inhibited by cyclosporin-A. Biochim. Biophys. Acta. 1187: 255-259.
110. Gulaya, N. M., A. A. Melnik, D. I. Balkov, G. L. Volkov, M. V. Vysotsky, and V. E. Vaskovsky. 1993. The effect of long-chain N-acylethanolamines on some membrane-associated functions of neuroblastoma C1300 N18 cells. Biochim. Biophys. Acta. 1152: 280-288.
111. Guzman, M., J. J. Fernandez-Ruiz, C. Sanchez, G. Velasco, and J. A. Ramos. 1995. Effects of anandamide on hepatic fatty acid metabolism. Biochem. Pharmacol. 50: 885-888.
112. Johnson, D. E., S. L. Heald, R. D. Dally, and R. A. Janis. 1993. Isolation, identification and synthesis of an endogenous arachidonic amide that inhibits calcium channel antagonist 1,4-dihydropyridine binding. Prostaglandins Leukot. Essent. Fatty Acids. 48: 429-437.
113. 2+ channel. Eur. J. Pharmacol. 296: 347-350.
114. Wartmann, M., D. Campbell, A. Subramanian, S. H. Burstein, and R. J. Davis. 1995. The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide. FEBS Lett. 359: 133-136.
115. Hillard, C. J., R. A. Harris, and A. S. Bloom. 1985. Effects of the cannabinoids on physical properties of brain membranes and phospholipid vesicles: fluorescence studies. J. Pharmacol. Exp. Ther. 232: 579-588.
116. Bloom, A. S., W. S. Edgemond, and J. C. Moldvan. 1997. Nonclassical and endogenous cannabinoids: effects on the ordering of brain membranes. Neurochem. Res. 22: 563-568.
117. DePetrocellis, L., P. Orlando, and V. DiMarzo. 1995. Anandamide, an endogenous cannabinomimetic substance, modulates rat brain protein kinase C in vitro. Biochem. Mol. Biol. Int. 36: 1127-1133.
118. Hillard, C. J., and J. A. Auchampach. 1994. In vitro activation of brain protein kinase C by the cannabinoids. Biochim. Biophys. Acta. 1220: 163-170.