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1-Arachidonoyl Glycerol-d5

Cayman Chemical Item Number 362152

1-AG-d5

1-Arachidonoyl Glycerol-d5

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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).

Synonyms
  • 1-AG-d5
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 forms (d1-d5)
Stability 6 months
Storage -80°C
Shipping Dry ice 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)​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 Price Quantity Subtotal
100 µg $27.00 $0.00
500 µg $122.00 $0.00
1 mg $216.00 $0.00
5 mg $945.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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Batch-specific Information

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FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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