Arachidonoyl ethanolamide (AEA) was the first endogenous cannabinoid to be isolated and characterized as an agonist acting on the same receptors (CB1 and CB2) as tetrahydrocannabinols (THC).1,2 Arachidonoyl cyclopropamide (ACPA) is a potent, stable, and selective agonist analog of AEA. ACPA has an Ki value of 2.2 nM at the isolated rat CB1 receptor, and is 325 times more potent at the CB1 receptor compared with the CB2 receptor.3 In whole animal experiments, ACPA induces hypothermia in mice with the same efficacy as AEA, in spite of its much higher affinity for the CB1 receptor. These data have been interpreted to indicate that ACPA may be a substrate for fatty acid amide hydrolase (FAAH), and thus only transiently available in whole animal experiments.3
1
Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science2581946-1949(1992).
2
Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA907656-7660(1993).
3
Hillard, C.J., Manna, S., Greenberg, M.J., et al. Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J Pharmacol Exp Ther2891427-1433(1999).
Room temperature
in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1CC1
Background Reading
Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science2581946-1949(1992).
Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA907656-7660(1993).
Hillard, C.J., Manna, S., Greenberg, M.J., et al. Synthesis and characterization of potent and selective agonists of the neuronal cannabinoid receptor (CB1). J Pharmacol Exp Ther2891427-1433(1999).
Arachidonoyl Cyclopropylamide is available in the following screening
library: