10007691  URB754

(CAS 86672-58-4)

Click image to enlarge


Chemical structure definitions are available for many Cayman products. See Chemical Structure Database for details.

2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the central cannabinoid (CB1) receptor.1,2 It is present at relatively high levels in the central nervous system and is the most abundant molecular species of monoacylglycerol found in rat brain.2,3 Monoacylglycerol lipase (MGL) hydrolyzes 2-AG to arachidonic acid and glycerol, thereby terminating its biological actions.4 URB754 is reported to be a potent, noncompetitive inhibitor of monoacylglycerol lipase (MAGL), exhibiting an IC50 of 200 nM for the recombinant rat brain enzyme.5 However, data from other labs indicates that it does not inhibit human recombinant, rat brain, or mouse brain MAGL at concentrations up to 100 µM.6,7 It inhibits rat brain fatty acyl amide hydrolase (FAAH) with an IC50 of 32 µM and binds weakly to the rat central cannabinoid (CB1) receptor with an IC50 of 3.8 µM.5 It does not inhibit cyclooxygenase-1 (COX-1) or COX-2 at concentrations up to 100 µM.5 Inhibition of 2-AG hydrolysis is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.8
1  Sugiura, T., Kodaka, T., Nakane, S., et al. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J Biol Chem 274 2794-2801 (1999).
2  Stella, N., Schweitzer, P., Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).
3  Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca2+-dependent and -independent mechanisms. FEBS Lett 429 152-156 (1998).
4  Dinh, T.P., Carpenter, D., Leslie, F.M., et al. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc Natl Acad Sci USA 99(16) 10819-10824 (2002).
5  Makara, J.K., Mor, M., Fegley, D., et al. Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus. Nature Neuroscience 8(9) 1139-1141 (2005).
6  Saario, S.M., Palomäki, V., Lehtonen, M., et al. URB754 has no effect on the hydrolysis or signaling capacity of 2-AG in the rat brain. Chemistry & Biology 13 811-814 (2006).
7  Vandevoorde, S., Jonsson, K., Labar, G., et al. Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysis in vitro. Br J Pharmacol 150 186-191 (2007).
8  Hohmann, A.G., Suplita, R.L., Bolton, N.M., et al. An endocannabinoid mechanism for stress-induced analgesia. Nature 435 1108-1112 (2005).


Purchase 10007691 URB754

Pricing is for North America only. Other customers should contact a distributor in their region.

This product is also available to buy in bulk quantities. Please contact our Sales Department for a quote or to purchase.

Cayman strives to be a reliable biochemical reagent vendor by providing the best possible products and services. To ask for assistance with one of our products please contact our Technical Help staff.

Warning This product is not for human or veterinary use.

Pricing updated 2010-03-18.
Prices are subject to change without notice.

Stability of this item is suitable for room temperature overnight shipping. If shipment on ice is desired, it must be requested when the order is placed.

  email: password: hide x LOGIN | REGISTER
Cayman Chemical
Topical Catalogs
Packed with articles, the latest products, and much more.

New
Eicosanoid


Allergy, Asthma, & Inflammation

Cancer

More...
Helping to make your research possible by providing quality biochemicals and assays for research in and much more.
toll free 800.364.9897
direct dial 734.971.3335
1180 East Ellsworth Road
Ann Arbor, Michigan 48108
USA