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.

VDM11

Cayman Chemical Item Number 10006731

(CAS 313998-81-1)

VDM11 (CAS 313998-81-1)

See more

Description

Numerous analogs of arachidonoyl ethanolamide (AEA) potentiate its biological activity. This potentiation is ascribed either to inhibition of AEA reuptake into neurons, or inhibition of fatty amide acyl hydrolase (FAAH) within the neurons.1,2 VDM11 is an AEA transport inhibitor with essentially no activity on either the central cannabinoid receptor (CB1), peripheral cannabinoid receptor (CB2), or the vanilloid receptor 1 (VR1).3 However, VDM11 inhibits FAAH and monoacylglycerol lipase (MAGL) and may act as an alternative FAAH substrate.4 At a concentration of 3 µM, VDM11, like AM404, inhibits glutamergic synaptic transmission between hippocampal neurons.5 The mechanism of this effect may be a direct action on sodium channels. Thus, the use of anandamide analogs as uptake inhibitors and interpretation of the results must be undertaken with care.

1 Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci 65 607-616 (1999).

2 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).

3 De Petrocellis, L., Bisogno, T., Davis, B.J., et al. Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: Inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett 483 52-56 (2000).

4 Vandervoorde, S., and Fowler, C.J. Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: Evidence that VDM11 acts as an FAAH substrate. Br J Pharmacol 145 885-893 (2005).

5 Kelley, B.G., and Thayer, S.A. Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors. Eur J Pharmacol 496 33-39 (2004).

Formal Name N-​(4-​hydroxy-​2-​methylphenyl)-​5Z,​8Z,​11Z,​14Z-​eicosatetraenamide
CAS Number 313998-81-1
Molecular Formula C27H39NO2
Formula Weight 409.6
Formulation A solution in ethanol
Purity >98%
λmax 202, 231 nm
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)​Nc1ccc(O)​cc1C

Background Reading

Khanolkar, A.D., and Makriyannis, A. Structure-activity relationships of anandamide, an endogenous cannabinoid ligand. Life Sci 65 607-616 (1999).

De Petrocellis, L., Bisogno, T., Davis, B.J., et al. Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: Inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett 483 52-56 (2000).

Vandervoorde, S., and Fowler, C.J. Inhibition of fatty acid amide hydrolase and monoacylglycerol lipase by the anandamide uptake inhibitor VDM11: Evidence that VDM11 acts as an FAAH substrate. Br J Pharmacol 145 885-893 (2005).

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).

Kelley, B.G., and Thayer, S.A. Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors. Eur J Pharmacol 496 33-39 (2004).

Show all 5 Hide all but first 3

VDM11 is available in the following screening library:

Size Price Quantity Subtotal
5 mg $33.00 $0.00
10 mg $63.00 $0.00
25 mg $149.00 $0.00
50 mg $264.00 $0.00
Bulk Contact
Cart Total $0.00

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

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

Pricing updated 2012-05-25. Prices are subject to change without notice.

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

AM1172
AM404
Arachidonoyl Ethanolamide
CAY10412 Exclusive
OMDM-1
OMDM-2
Show all 6 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?