NAGLY Chemical Properties

Boiling point:

560.9±50.0 °C(Predicted)

Density 

0.985±0.06 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

DMSO: >5 mg/mL, soluble

form 

waxy solid

pka

3.58±0.10(Predicted)

color 

off-white

Sensitive 

Air Sensitive

Stability:

Stable for 2 years from date of purchase as supplied. Product is subject to oxidation. Solutions in degassed DMSO may be stored at -20°C for up to 1 month.

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

NAGLY Usage And Synthesis

Description

Arachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide), from extracts of mammalian brain, and has also been synthesized as an analog of AEA for structure/activity testing. NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl CoA. NAGly is reported to have analgesic activities in whole animal experiments. Since it seems to be a very poor ligand for the CB₁ receptor, these effects are probably mediated via other signaling pathways.

Uses

Arachidonoyl glycine (N-arachidonyl glycine; NAGly) has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA; anandamide), from extracts of mammalian brain, and has also been synthesized as an analog of AEA for structure/activity testing. NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl CoA. NAGly is reported to have analgesic activities in whole animal experiments. Since it seems to be a very poor ligand for the CB1 receptor, these effects are probably mediated via other signaling pathways.[Cayman Chemical]

Uses

An endogenous anandamide-like compound; also acts as a T-type Ca2+ channel blocker and an endogenous GLYT2 inhibitor.

Definition

ChEBI: N-arachidonoylglycine is biologically active derivative of anandamide It is a N-acylglycine and a fatty amide. It is functionally related to an arachidonic acid. It is a conjugate acid of a N-arachidonoylglycinate.

Biological Activity

Endogenous anandamide-like compound. Lacks affinity for CB 1 receptors (K i > 10 μ M), VR1 receptors (EC 50 > 10 μ M) and anandamide transporters (IC 50 > 50 μ M) but causes hot-plate analgesia in mice when given orally, and suppresses tonic inflammatory pain. Also endogenous GlyT2 inhibitor.

storage

-20°C (desiccate)

References

[1] SUSAN M. HUANG. Identification of a New Class of Molecules, the Arachidonyl Amino Acids, and Characterization of One Member That Inhibits Pain*[J]. The Journal of Biological Chemistry, 2001, 19 1: 42639-42644. DOI:10.1074/jbc.m107351200
[2] DOUGLAS MCHUGH. Δ(9) -Tetrahydrocannabinol and N-arachidonyl glycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells.[J]. British Journal of Pharmacology, 2012: 2414-2424. DOI:10.1111/j.1476-5381.2011.01497.x
[3] DOUGLAS MCHUGH. siRNA knockdown of GPR18 receptors in BV-2 microglia attenuates N-arachidonoyl glycine-induced cell migration.[J]. Journal of Molecular Signaling, 2012, 7 1: 10. DOI:10.1186/1750-2187-7-10
[4] RINA TAKENOUCHI. N-arachidonoyl glycine induces macrophage apoptosis via GPR18[J]. Biochemical and biophysical research communications, 2012, 418 2: Pages 366-371. DOI:10.1016/j.bbrc.2012.01.027
[5] SUMNER H. BURSTEIN. Resolution of inflammation by N-arachidonoylglycine[J]. Journal of cellular biochemistry, 2011, 112 11: 3227-3233. DOI:10.1002/jcb.23245
[6] LINDA CONSOLE-BRAM . N-arachidonoyl glycine, another endogenous agonist of GPR55[J]. Biochemical and biophysical research communications, 2017, 490 4: Pages 1389-1393. DOI:10.1016/j.bbrc.2017.07.038

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