390824-17-6

Basic information

• Product Name: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER
• Synonyms: CAY10412;5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER;YOPBWSZRYHDZAA-DOFZRALJSA-N
• CAS NO: 390824-17-6
• Molecular Formula: C25H36O2S
• Molecular Weight: 400.62
• Mol File: 390824-17-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER(390824-17-6)
• EPA Substance Registry System: 5Z,8Z,11Z,14Z-EICOSATETRAENOIC ACID, 3-THIENYLMETHYL ESTER(390824-17-6)

Safety Data

• Hazardous Substances Data: 390824-17-6(Hazardous Substances Data)

Usage

Uses

Anandamide (arachidonoyl ethanolamide; AEA) is an endogenous lipid with cannabinergic activity; along with 2-arachidonoyl glycerol, it forms part of the endocannabinoid system. AEA undergoes reuptake into neurons by a facilitated process. Controversy exists as to whether there is a specific AEA transporter, or instead the uptake process is simply driven by hydrolysis of AEA by intracellular fatty acyl amide hydrolase (FAAH). CAY10412 is an analog of AEA that has no intrinsic binding affinity for either CB1 or CB2 receptors. It is a potent inhibitor of AEA reuptake in U937 lymphoma cells, with an IC50 of 3 μM. CAY10412 could be a useful tool for distinguishing the competing transporter theories. The pharmacology of CAY10412 is largely unexplored; it may enhance endocannabinoid signalling by augmenting endocannabinoid concentrations.

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 71637-34-8 3-hydroxymethyl-thiophene 
• 57303-04-5 arachidonoyl chloride 

Relevant articles and documents

Design, synthesis and biological evaluation of new endocannabinoid transporter inhibitors

In the present work we describe the synthesis and the in vitro evaluation of a series of arachidonic acid derivatives of general structure I as endocannabinoid transporter inhibitors. In addition, we report the first in vivo studies of the most potent derivative (4, UCM707) within this series. The majority of compounds studied are highly potent (IC50=24-0.8 μM) and selective endocannabinoid uptake inhibitors with very low affinities for either the enzyme fatty acid amide hydrolase (IC50=30-113 μM) or for cannabinoid receptor subtype 1 (CB1), cannabinoid receptor subtype 2 (CB2) and vanilloid receptor subtype 1 (VR1) (Ki=1000-10000 nM). Among them, (5Z,8Z,11Z,14Z)-N-(fur-3-ylmethyl)icosa-5,8,11,14-tetraenamide (UCM707) behaves as the most potent endocannabinoid transporter inhibitor described to date (IC50=0.8 μM) and exhibits improved potency for the anandamide transporter, high selectivity for CB1 and VR1 receptors, and modest selectivity for CB2. In vivo it enhances the analgesia and hypokinetic effects induced by a subeffective dose of anandamide.

Design, synthesis, and biological evaluation of new inhibitors of the endocannabinoid uptake: Comparison with effects on fatty acid amidohydrolase

A new series of arachidonic acid derivatives were synthesized and evaluated as inhibitors of the endocannabinoid uptake. Most of them are able to inhibit anandamide uptake with IC50 values in the low micromolar range (IC50 = 0.8-24 μM). ln general, the compounds had only weak effects upon CB1, CB2, and VR1 receptors (Ki > 1000-10000 nM). In addition, there was no obvious relationship between the abilities of the compounds to affect anandamide uptake and to inhibit anandamide metabolism by fatty acid amidohydrolase (FAAH; IC50 = 30-113 μM). This indicates that the compounds do not exert their effects secondarily to FAAH inhibition. It is hoped that these compounds, particularly the most potent in this series (compound 5, UCM707, with IC50 values for anandamide uptake and FAAH of 0.8 and 30 μM, respectively), will provide useful tools for the elucidation of the role of the anandamide transporter system in vivo.