179113-91-8 Usage
Description
Arachidonoyl glycine (N-arachidonyl glycine; NAGLY) is an endogenous anandamide-like compound that 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. It is reported to have analgesic activities in whole animal experiments and acts as a T-type Ca2+ channel blocker and an endogenous GLYT2 inhibitor.
Uses
Used in Pharmaceutical Industry:
NAGLY is used as an analgesic agent for its pain-relieving properties in whole animal experiments. Its effects are likely mediated via other signaling pathways, as it is a very poor ligand for the CB1 receptor.
Used in Neurological Research:
NAGLY is used as a T-type Ca2+ channel blocker, which helps in studying the role of these channels in various neurological processes and disorders.
Used in Neurotransmission Studies:
NAGLY is used as an endogenous GLYT2 inhibitor, which aids in understanding the regulation of neurotransmission and the role of GLYT2 in neurological conditions.
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.
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]
Check Digit Verification of cas no
The CAS Registry Mumber 179113-91-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,9,1,1 and 3 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 179113-91:
(8*1)+(7*7)+(6*9)+(5*1)+(4*1)+(3*3)+(2*9)+(1*1)=148
148 % 10 = 8
So 179113-91-8 is a valid CAS Registry Number.
179113-91-8Relevant articles and documents
A Convenient Protocol for the Synthesis of Fatty Acid Amides
Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.
supporting information, p. 213 - 217 (2019/01/14)
Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.