URB754
Cayman Chemical Item Number 10007691
(CAS 86672-58-4)
URB754
(CAS 86672-58-4)
| Formal Name |
6-methyl-2-[(4-methylphenyl)amino]-1-benzoxazin-4-one |
| CAS Number |
86672-58-4 |
| Molecular Formula |
C16H14N2O2 |
| Formula Weight |
266.3 |
| Formulation |
A crystalline solid |
| Purity |
>98% |
| λmax |
216, 247, 283, 348 nm |
| Stability |
2 years |
| Storage |
-20°C |
| Shipping |
Wet Ice
in continental US; may vary elsewhere
|
| SMILES |
Cc1ccc(cc1)Nc1nc2ccc(C)cc2c(=O)o1
|
Description
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. Nat Neurosci 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. Chem Biol 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).
Related Articles
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).
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).
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).
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. Chem Biol 13 811-814 (2006).
Stella, N., Schweitzer, P., Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).
Makara, J.K., Mor, M., Fegley, D., et al. Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus. Nat Neurosci 8(9) 1139-1141 (2005).
Hohmann, A.G., Suplita, R.L., Bolton, N.M., et al. An endocannabinoid mechanism for stress-induced analgesia. Nature 435 1108-1112 (2005).
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).
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Pricing updated 2010-09-09.
Prices are subject to change without notice.
Pricing is for North America only. Other customers should contact a distributor in their region.
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