| References |
| Synonyms |
|
| Formal Name |
5Z,8Z,11Z,14Z-eicosatetraenoic acid, 1-glycerol-1,1,2,3,3-d5 ester |
| Molecular Formula |
C23H33D5O4 |
| Formula Weight |
383.6 |
| Formulation |
A solution in acetonitrile |
| Purity |
≥99% deuterated product |
| Stability |
6 months |
| Storage |
-80°C |
| Shipping |
Dry ice
in continental US; may vary elsewhere
|
| SMILES |
CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)OC(CO)CO
|
Background Reading
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 Commun 229 58-64 (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 Biochem 122 890-895 (1997).
| Size |
Global Purchasing |
| 100 µg |
|
| 500 µg |
|
| 1 mg |
|
| 5 mg |
|
Description
1-Arachidonoyl glycerol-d5 (1-AG-d5) contains five deuterium atoms at the 1, 1, 2, 3, and 3 positions of the glycerol moiety. It is intended for use as an internal standard for the quantification of 1-AG by GC- or LC-mass spectrometry. The glyceryl esters of arachidonic acid have been proposed as endogenous cannabinoid ligands.1 2-AG is 10 to 100 times more potent than 1-AG in ligand binding affinity and agonist activity at the CB1 receptor,2 and is thus considered to be the natural ligand. However, 2-AG is chemically unstable and undergoes rapid isomerization to 1-AG (synonymous with 1(3)-AG) both in vitro and in vivo. 1-AG is a frequent contaminant in synthetic 2-AG preparations, and can markedly reduce their cannabinergic potency. 1-AG is a weak CB1 receptor agonist and may have other pharmacologic properties.
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 Commun 229 58-64 (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 Biochem 122 890-895 (1997).
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