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Arachidoyl Ethanolamide
Cayman Chemical Item Number 10005765
Description
The endocannabinoids1↗,2↗ present a rich system of central cannabinoid (CB1), peripheral cannabinoid (CB2), and non-CB receptor-mediated pharmacology that has stimulated research in many fields including memory, weight loss and appetite, neurodegeneration, tumor surveillance, analgesia, and inflammation. Arachidoyl ethanolamide is one of the saturated fatty acyl ethanolamides devoid of classical (CB1/CB2) activity. Arachidoyl ethanolamide does not bind to the murine CB1 receptor3↗ and does not compete with anandamide as a substrate for the endocannabinoid hydrolytic enzyme fatty acid amide hydrolase.4↗ Non-CB receptor-mediated pharmacology of the saturated ethanolamides is still being elucidated.5↗
1 Martin, B.R., Mechoulam, R., and Razdan, R.K. Discovery and characterization of endogenous cannabinoids. Life Sci 65 573-595 (1999).
2 Pertwee, R.G. Pharmacology of cannabinoid receptor ligands. Curr Med Chem 6 635-664 (1999).
3 Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 659-667 (1997).
4 Desarnaud, F., Cadas, H., and Piomelli, D. Anandamide amidohydrolase activity in rat brain microsomes. Identification and partial characterization. J Biol Chem 270(11) 6030-6035 (1995).
5 Smart, D., Jonsson, K., Vandevoorde, S., et al. “Entourage” effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism.. Br J Pharmacol 136 452-458 (2002).
Synonyms N-Arachidoylethanolamine
Formal Name N-(2-hydroxyethyl)-eicosanamide
CAS Number 94421-69-9
Molecular Formula C22H45NO2
Formula Weight 355.6
Formulation A crystalline solid
Purity >98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CCCCCCCCCCCCCCCCCCCC(=O)NCCO
InCHI Code 1S/C22H45NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h24H,2-21H2,1H3,(H,23,25)
InCHI Key AUJVQJHODMISJP-UHFFFAOYSA-N |