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N-Arachidonoyl-L-Serine

Cayman Chemical Item Number 10005455

ARA-S (CAS 187224-29-9)

N-Arachidonoyl-L-Serine (CAS 187224-29-9)

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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.

1 Bisogno, T., Melck, D., Bobrov, M.Y., et al. N-acyl-dopamines: Novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J 351 817-824 (2001).

2 Milman, G., Maor, Y., Horowitz, M., et al. Arachidonoyl-serine, an endocannabinoid-like bioactive constituent of rat brain. 14th Annual Symposium on the Cannabinoids 133 (2004).

3 Milman, G., Maor, Y., Abu-Lafi, S., et al. N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties. Proc Natl Acad Sci USA 103(7) 2428-2433 (2006).

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
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​N[C@@H]​(CO)​C(=O)​O

Background Reading

Bisogno, T., Melck, D., Bobrov, M.Y., et al. N-acyl-dopamines: Novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem J 351 817-824 (2001).

Milman, G., Maor, Y., Horowitz, M., et al. Arachidonoyl-serine, an endocannabinoid-like bioactive constituent of rat brain. 14th Annual Symposium on the Cannabinoids 133 (2004).

Milman, G., Maor, Y., Abu-Lafi, S., et al. N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties. Proc Natl Acad Sci USA 103(7) 2428-2433 (2006).

N-Arachidonoyl-L-Serine is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $15.00 $0.00
5 mg $60.00 $0.00
10 mg $90.00 $0.00
25 mg $169.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-25. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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