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N-Arachidonoyl-L-Serine
Cayman Chemical Item Number 10005455
Description
Arachidonoyl amides of both amino acids and neurotransmitters such as dopamine have been previously reported in the literature.1↗ N-Arachidonoyl-L-serine (ARA-S) is one such recently isolated endocannabinoid with an unusual activity profile. ARA-S does not bind to central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors or vanilloid receptor 1 (VR1). Like cannabidiol, ARA-S (5 mg/kg) antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol (Abn-CBD) in an anesthetized rat blood pressure model.2↗ However, similar to Abn-CBD, ARA-S relaxes isolated rat mesenteric arteries and abdominal aorta as well as increases phosphorylation of Akt and mitogen-activated protein kinase (MAPK) in HUVEC.3↗ The precise mechanisms of action by ARA-S and Abn-DBD in various vascular preparations appears to be different and requires further investigation.
Synonyms ARA-S
Formal Name N-[1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl]-L-serine
CAS Number 187224-29-9
Molecular Formula C23H37NO4
Formula Weight 391.5
Formulation A solution in ethanol
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@@H](CO)C(=O)O
InCHI Code 1S/C23H37NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(26)24-21(20-25)23(27)28/h6-7,9-10,12-13,15-16,21,25H,2-5,8,11,14,17-20H2,1H3,(H,24,26)(H,27,28)/b7-6-,10-9-,13-12-,16-15-
InCHI Key FQUVPTVNRMUOPO-DOFZRALJSA-N |