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URB602

Cayman Chemical Item Number 10007457

(CAS 565460-15-3)

URB602 (CAS 565460-15-3)

See more	Cannabinoids (333) Forensic Science (369) Inflammation (396) Neuroscience (725)

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%
λ_max	236 nm
Stability	2 years
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard 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
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-05-25. 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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