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HomeProduct name listNAGLY

NAGLY

Synonym(s):methylene chloride solution;N-[(5Z,8Z,11Z,14Z)-1-oxo-5,8,11,14-eicosatetraen-1-yl]-glycine

NAGLY Structural

What is NAGLY?

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.

The Uses of NAGLY

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]

The Uses of NAGLY

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

What are the applications of Application

N-Arachidonoyl glycine (solution in ethanol) is a compound that lacks affinity for CB1 receptors but inhibits FAAH

What are the applications of Application

N-Arachidonoyl glycine is an endogenous anandamide-like compound

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) Huang et al. (2001), Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain; J. Biol. Chem., 276 42639 2) McHugh et al. (2012), Δ(9)-Tetrahydrocannabinol and N-arachidonylglycine are full agonists at GPR18 receptors and induce migration in human endometrial HEC-1B cells; Br. J. Pharmacol., 165 2414 3) McHugh et al. (2012), siRNA knockdown of GPR18 receptors in BV-2 microglia attenuates N-arachidonyl glycine-induced cell migration; J. Mol. Signal., 7 10 4) Takenouchi et al. (2012), N-arachidonyl glycine induces macrophage apoptosis via GPR18; Biochem. Biophys. Res. Commun., 418 366 5) Burstein et al. (2011), Resolution of inflammation by N-arachidonoylglycine; J. Cell Biochem., 112 3227 6) Console-Bram et al. (2017), N-arachidonoyl glycine, another endogenous agonist of GPR55; Biochem. Biophys. Res. Commun., 490 1389 [FOCUS CITATION]

Properties of NAGLY

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 for NAGLY

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H336:Specific target organ toxicity,single exposure; Narcotic effects
H351:Carcinogenicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for NAGLY

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