187224-29-9

Basic information

• Product Name: ARA-S
• Synonyms: N-ARACHIDONOYL L-SERINE;ARA-S;N-[1-OXO-(5Z,8Z,11Z,14Z-EICOSATETRAENYL)]-L-SERINE
• CAS NO: 187224-29-9
• Molecular Formula: C23H37NO4
• Molecular Weight: 391.54
• Product Categories: Cannabinoid receptor
• Mol File: 187224-29-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ARA-S(CAS DataBase Reference)
• NIST Chemistry Reference: ARA-S(187224-29-9)
• EPA Substance Registry System: ARA-S(187224-29-9)

Safety Data

• Hazardous Substances Data: 187224-29-9(Hazardous Substances Data)

Usage

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)

Upstream product

• 56-45-1 L-serin 
• 55726-28-8 arachidonic acid anhydride 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 312-84-5 D-Serine 
• 187224-28-8 (5Z,8Z,11Z,14Z)-2,5-dioxopyrrolidin-1-yl icosa-5,8,11,14-tetraenoate 
• 26348-61-8 L-serine ethyl ester hydrochloride 

Relevant articles and documents

Identification of endogenous acyl amino acids based on a targeted lipidomics approach

Using a partially purified bovine brain extract, our lab identified three novel endogenous acyl amino acids in mammalian tissues. The presence of numerous amino acids in the body and their ability to form amides with several saturated and unsaturated fatty acids indicated the potential existence of a large number of heretofore unidentified acyl amino acids. Reports of several additional acyl amino acids that activate G-protein coupled receptors (e.g., N-arachidonoyl glycine, N- arachidonoyl serine) and transient receptor potential channels (e.g., N-arachidonoyl dopamine, N-acyl taurines) suggested that some or many novel acyl amino acids could serve as signaling molecules. Here, we used a targeted lipidomics approach including specific enrichment steps, nano-LC/MS/MS, high-throughput screening of the datasets with a potent search algorithm based on fragmention analysis, and quantification using the multiple reaction monitoring mode in Analyst software to measure the biological levels of acyl amino acids in rat brain. We successfully identified 50 novel endogenous acyl amino acids present at 0.2 to 69 pmol g-1 wet rat brain. Copyright

Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor

In order to establish the structural requirements for binding to the brain cannabinoid receptor (CB1), we have synthesized numerous fatty acid amides, ethanolamides, and some related simple derivatives and have determined their K(i) values. A f