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Arachidonoyl Serinol

Katalog-Nr.GC18097

CB1 receptor agonist

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Arachidonoyl Serinol Chemische Struktur

Cas No.: 183718-70-9

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Sample solution is provided at 25 µL, 10mM.

Description of Arachidonoyl Serinol

Arachidonoyl Serinol is an amide bond-containing analogue of 2-arachidonoylglycerol, exhibited only weak CB1 receptor agonistic activity. 2-Arachidonoyl glycerol (2-AG), a product of increased inositol phospholipid metabolism, is the natural endocannabinoid ligand for the CB1 receptor [1][2][3].

Cannabinoid receptor (CB1) was first identified in rat brain in 1988. N-arachidonoylethanolamine (anandamide) binds to the cannabinoid receptor and exhibits various cannabimimetic activities. Anandamide inhibits calcium currents in N18 neuroblastoma cells, inhibits forskolin-stimulated adenylase cyclase activity, electrically evokes twitch response of the mouse vas deferens, and causes analgesia, hypothermia, hypoactivity, and catalepsy [3]. Anandamide acts as a weak agonist and 2-arachidonoylglycerol may be an endogenous cannabinoid receptor agonist in nervous tissues [1].

Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom produces Arachidonoyl Serinol. In NG108-15 cells, Arachidonoyl Serinol induced a weak elevation of [Ca2+]I [1][2].

References:
[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. 1996 Dec 4;229(1):58-64.
[2].  Sugiura T1, 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. 1997 Oct;122(4):890-5.
[3].  Khanolkar AD, Abadji V, Lin S, et al. Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9.

Chemical Properties of Arachidonoyl Serinol

Cas No. 183718-70-9 SDF
Chemical Name N-[(2-hydroxy-1-hydroxymethyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
Canonical SMILES O=C(NC(CO)CO)CCC\C=C/C/C=C\C/C=C\C/C=C\CCCCC
Formula C23H39NO3 M.Wt 377.6
Löslichkeit ≤10mg/ml in ethanol;10mg/ml in DMSO;10mg/ml in dimethyl formamide Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Arachidonoyl Serinol

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1 mg 5 mg 10 mg
1 mM 2.6483 mL 13.2415 mL 26.4831 mL
5 mM 0.5297 mL 2.6483 mL 5.2966 mL
10 mM 0.2648 mL 1.3242 mL 2.6483 mL
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