390824-20-1

Basic information

• Product Name: (5Z,8Z,11Z,14Z)-N-(3-FURANYLMETHYL)-5,8,11,14-EICOSATETRAENAMIDE
• Synonyms: N-(3-FURANYLMETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE;UCM 707;(5Z,8Z,11Z,14Z)-N-(3-FURANYLMETHYL)-5,8,11,14-EICOSATETRAENAMIDE;(5Z,8Z,11Z,14Z)-N-(furan-3-ylmethyl)icosa-5,8,11,14-tetraenamide
• CAS NO: 390824-20-1
• Molecular Formula: C25H37NO2
• Molecular Weight: 383.57
• Product Categories: Cannabinoid receptor
• Mol File: 390824-20-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 538.9±50.0 °C(Predicted)
• Appearance: /
• Density: 0.961±0.06 g/cm3(Predicted)
• Storage Temp.: Desiccate at -20°C
• PKA: 15.74±0.46(Predicted)
• CAS DataBase Reference: (5Z,8Z,11Z,14Z)-N-(3-FURANYLMETHYL)-5,8,11,14-EICOSATETRAENAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z,8Z,11Z,14Z)-N-(3-FURANYLMETHYL)-5,8,11,14-EICOSATETRAENAMIDE(390824-20-1)
• EPA Substance Registry System: (5Z,8Z,11Z,14Z)-N-(3-FURANYLMETHYL)-5,8,11,14-EICOSATETRAENAMIDE(390824-20-1)

Safety Data

• Hazardous Substances Data: 390824-20-1(Hazardous Substances Data)

Usage

Uses

UCM 707 is a selective inhibitor of anandamide uptake.

Biological Activity

Potent endocannabinoid transport inhibitor. IC 50 values are 0.8 and 30 μ M for inhibition of the anandamide transporter and FAAH respectively. K i values are 4700, 67 and > 5000 nM for CB 1 , CB 2 and VR1 receptors respectively. Potentiates hypokinetic and antinociceptive effects of anandamide in vivo .

Upstream product

• 57303-04-5 arachidonoyl chloride 
• 4543-47-9 3-furylmethylamine 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 498-60-2 furan-3-carboxaldehyde 
• 4412-91-3 furan-3-methanol 

Relevant articles and documents

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.

Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors

In the present work, we have designed and synthesized a series of arachidonic acid derivatives of general structure I which have been characterized as highly potent and selective inhibitors of anandamide transporter (IC50 = 24-0.8 μM, Ki > 1000-5000 nM for CB1 and CB2 cannabinoid receptors and vanilloid VR1 receptor). Among them, N-(3-furylmethyl)eicosa-5,8,11,14-tetraenamide deserves special attention as being the most potent endocannabinoid transporter inhibitor (IC50 = 0.8 μM) described to date.