ARA-S Chemical Properties

Boiling point:

607.6±55.0 °C(Predicted)

Density 

1.027±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 2 mg/ml

pka

3.26±0.10(Predicted)

ARA-S Usage And Synthesis

Description

Arachidonoyl amides of both amino acids and neurotransmitters such as dopamine have been previously reported in the literature. 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. 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. The precise mechanisms of action by ARA-S and Abn-DBD in various vascular preparations appears to be different and requires further investigation.

Uses

N-Arachidonoyl-L-serine is a novel neuroprotective endocannabinoid with weak affinity for CB1 and CB2 cannabinoid receptors. It is also a pro-angiogenic factor and a vessel dilator. Shows proneurogenic properties in vitro and invivo in mice model of traumatic brain injury. (1) Exhibits neuroprotection via ERK and Akt phosphorylation and induction of their downstream antiapoptotic pathways (2)

Definition

ChEBI: N-arachidonoyl-L-serine is an N-acyl-amino acid resulting from the formal condensation of the carboxy group of arachidonic acid with the amino group of L-serine. It is an endocannabinoid-like lipid isolated from bovine brains. It has a role as a cannabinoid receptor agonist, a vasodilator agent, a pro-angiogenic agent, a neuroprotective agent and a mammalian metabolite. It is functionally related to an arachidonic acid and a L-serine. It is a conjugate acid of a N-arachidonoyl-L-serine(1-).

References

[1] T BISOGNO. N-acyl-dopamines: novel synthetic CB(1) cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo.[J]. Biochemical Journal, 2000, 351 Pt 3: 817-824.
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] GARRY MILMAN. N-arachidonoyl L-serine, an endocannabinoid-like brain constituent with vasodilatory properties.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2006: 2428-2433. DOI: 10.1073/pnas.0510676103

ARA-S(187224-29-9)Related Product Information

• R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
• ANANDAMIDE
• ARA-S
• NAGLY
• N-(1-OXO-5Z,8Z,11Z,14Z-EICOSATETRAENYL)-L-ALANINE