2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.1,2 Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol.3 Arachidonoyl serinol is much more stable than 2-AG. However, it is at least a log less potent as a CB1 receptor agonist than 2-AG.2
1
Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem Biophys Res Commun22958-64(1996).
2
Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem122890-895(1997).
3
Khanolkar, A.D., Abadji, V., Lin, S., et al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem394515-4519(1996).
Room temperature
in continental US; may vary elsewhere
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O=C(NC(CO)CO)CCC\C=C/C/C=C\C/C=C\C/C=C\CCCCC
Background Reading
Khanolkar, A.D., Abadji, V., Lin, S., et al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem394515-4519(1996).
Sugiura, T., Kodaka, T., Kondo, S., et al. 2-Arachidonoylglycerol, a putative endogenous cannabinoid receptor ligand, induces rapid, transient elevation of intracellular free Ca2+ in neuroblastoma X glioma hybrid NG108-15 cells. Biochem Biophys Res Commun22958-64(1996).
Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB1 receptor a 2-arachidonoylglycerol receptor? Structural requirements for triggering a Ca2+ transient in NG108-15 cells. J Biochem122890-895(1997).
Arachidonoyl Serinol is available in the following screening
library: