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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

URB602

Cayman Chemical Item Number 10007457

(CAS 565460-15-3)

URB602 (CAS 565460-15-3)

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Description

2-Arachidonoyl glycerol (2-AG) is an endogenous agonist of the cannabinoid receptor 1 (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.1,3 Monoglycerol lipase (MGL) hydrolyzes 2-AG to arachidonic acid and glycerol, thereby terminating its biological actions.4 URB602 is a selective inhibitor of MGL, exhibiting an IC50 of 28 µM for the rat brain enzyme.5 It does not inhibit fatty acid amide hydrolase (FAAH) at concentrations up to 100 µM, or other lipid metabolizing enzymes such as diacylglycerol lipase or cyclooxygenase-2.5,6 Inhibition of 2-AG hydrolysis is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.5

1 Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

2 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).

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 Hohmann, A.G., Suplita, R.L., Bolton, N.M., et al. An endocannabinoid mechanism for stress-induced analgesia. Nature 435 1108-1112 (2005).

6 Tarzia, G., Duranti, A., Tontini, A., et al. Design, Synthesis, and strcture-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors. J Med Chem 46 2352-2360 (2003).

Formal Name [1,​1'-​biphenyl]-​3-​yl-​carbamic acid,​ cyclohexyl ester
CAS Number 565460-15-3
Molecular Formula C19H21NO2
Formula Weight 295.4
Formulation A crystalline solid
Purity >98%
λmax 236 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(OC1CCCCC1)​Nc1cccc(c1)​c1ccccc1

Background Reading

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).

Hohmann, A.G., Suplita, R.L., Bolton, N.M., et al. An endocannabinoid mechanism for stress-induced analgesia. Nature 435 1108-1112 (2005).

Tarzia, G., Duranti, A., Tontini, A., et al. Design, Synthesis, and strcture-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors. J Med Chem 46 2352-2360 (2003).

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).

Stella, N., Schweitzer, P., and Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388 773-778 (1997).

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).

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Size Price Quantity Subtotal
5 mg $28.00 $0.00
10 mg $53.00 $0.00
50 mg $224.00 $0.00
100 mg $392.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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