2-Arachidonoyl Glycerol-d8

2-Arachidonoyl Glycerol-d₈

Cayman Chemical Item Number 362160

2-AG-d₈

Description

2-Arachidonoyl glycerol-d₈ (2-AG-d₈) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions of the arachidonic acid moiety. It is intended for use as an internal standard for the quantification of 2-AG by GC- or LC-mass spectrometry. 2-AG is an endogenous agonist of the CB₁ receptor.^1,2 Unlike anandamide, 2-AG is present at relatively high levels in the central nervous system; it is the most abundant molecular species of monoacylglycerol found in rat brain.^1,3 Formation of 2-AG is calcium-dependent and is mediated by the activities of phospholipase C and diacylglycerol lipase.¹ 2-AG acts as a full agonist at the CB₁ receptor. At a concentration of 0.3 nM, 2-AG induces a rapid, transient increase in intracellular free calcium in NG108-15 neuroblastoma X glioma cells through a receptor-dependent mechanism.⁴

1 Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

2 Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB₁ receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).

3 Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).

4 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

2-AG-d8

Formal Name

5Z,8Z,11Z,14Z-eicosatetraenoic-5,6,8,9,11,12,14,15-d8 acid, 2-glyceryl ester

Molecular Formula

C₂₃H₃₀D₈O₄

Formula Weight

386.6

Formulation

A solution in acetonitrile

Purity

≥99% deuterated forms (d1-d8)

Stability

6 months

Storage

-80°C

Shipping

Dry ice in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

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. 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).

Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB₁ receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).

Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).

Show all 4 Hide all but first 3

Size

Price

Quantity

Subtotal

25 µg 
$57.00

$0.00

50 µg 
$108.00

$0.00

100 µg 
$205.00

$0.00

500 µg 
$912.00

$0.00

Bulk
Contact

Cart Total

$0.00

Other Resources

Management Team Company Profile Company History ChemAssistant Tools FAQs

Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases

Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule

Order Terms Browser Recommendation Privacy Statement Site Map

2-Arachidonoyl Glycerol-d₈