See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Holiday Notification: Cayman Chemical will be closed Monday, May 28, 2012, in observance of the Memorial Day holiday. More…
Please feel free to continue placing orders via our website or via fax at 734-971-3640. You may send an email to customer service at custserv@caymanchem.com , or to technical support at techserv@caymanchem.com which we will respond to the next business day. Cayman will resume regular business hours and shipping schedules on Tuesday, May 29, 2012. Thank you for your patience and understanding.

CAY10412 Exclusive

Cayman Chemical Item Number 72620

(CAS 390824-17-6)

CAY10412 (CAS 390824-17-6)

See more

Description

Anandamide (arachidonoyl ethanolamide; AEA) is an endogenous lipid with cannabinergic activity; along with 2-arachidonoyl glycerol, it forms part of the endocannabinoid system.1,2 AEA undergoes reuptake into neurons by a facilitated process.3 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).4,5 CAY10412 is an analog of AEA that has no intrinsic binding affinity for either CB1 or CB2 receptors.6 It is a potent inhibitor of AEA reuptake in U937 lymphoma cells, with an IC50 of 3 µM.6 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.

1 Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946-1949 (1992).

2 Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).

3 Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. J Biol Chem 276(10) 6967-6973 (2001).

4 Beltramo, M., Stella, N., Calignano, A., et al. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 277 1094-1097 (1997).

5 Glaser, S.T., Abumrad, N.A., Fatade, F., et al. Evidence against the presence of an anandamide transporter. Proc Natl Acad Sci USA 100(7) 4269-4274 (2003).

6 López-Rodriguez, M.L., Viso, A., Ortega-Gutiérrez, S., et al. Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors. J Med Chem 44 4505-4508 (2001).

Formal Name 5Z,​8Z,​11Z,​14Z-​eicosatetraenoic acid,​ 3-​theinylmethyl ester
CAS Number 390824-17-6
Molecular Formula C25H36O2S
Formula Weight 400.6
Formulation A solution in methyl acetate
Purity >98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)​OCc1cscc1

Background Reading

Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946-1949 (1992).

Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90 7656-7660 (1993).

Beltramo, M., Stella, N., Calignano, A., et al. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 277 1094-1097 (1997).

López-Rodriguez, M.L., Viso, A., Ortega-Gutiérrez, S., et al. Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors. J Med Chem 44 4505-4508 (2001).

Deutsch, D.G., Glaser, S.T., Howell, J.M., et al. The cellular uptake of anandamide is coupled to its breakdown by fatty-acid amide hydrolase. J Biol Chem 276(10) 6967-6973 (2001).

Glaser, S.T., Abumrad, N.A., Fatade, F., et al. Evidence against the presence of an anandamide transporter. Proc Natl Acad Sci USA 100(7) 4269-4274 (2003).

Show all 6 Hide all but first 3

CAY10412 is available in the following screening library:

Size Global Purchasing
5 mg See a distributor in your region for pricing
10 mg See a distributor in your region for pricing
50 mg See a distributor in your region for pricing
100 mg See a distributor in your region for pricing

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

AM404
Arachidonoyl Ethanolamide
Arachidonoyl Serotonin
Arvanil
N-Arachidonoyl Dopamine
Oleoyl Ethanolamide
Olvanil
Palmitoyl Ethanolamide
Show all 8 Hide all but first 3

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?