URB754 (CAS 86672-58-4) | Cayman Chemical
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URB754

Item № 10007691
CAS № 86672-58-4
Purity >98%
product image
                (CAS 86672-58-4)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $28.00 0.00
     10 mg $53.00 0.00
     50 mg $224.00 0.00
     100 mg $392.00 0.00

Pricing updated 2018-11-19. Prices are subject to change without notice.

Description

URB754 is a potent and noncompetitive inhibitor of monoacylglycerol lipase (MAGL), exhibiting an IC50 value of 200 nM for the recombinant rat brain enzyme.1 However, it does not inhibit human recombinant, rat brain, or mouse brain MAGL at concentrations up to 100 µM.2,3 There is evidence that the MAGL inhibitory activity of URB754 may be attributed to the impurity bis(methylthio)mercurane (IC50 = 11.9 nM for rat recombinant MAGL) that is found in commercial preparations.4 URB754 inhibits rat brain fatty acyl amide hydrolase (FAAH) with an IC50 value of 32 µM and binds weakly to the rat central cannabinoid (CB1) receptor with an IC50 value of 3.8 µM.1 It does not inhibit COX-1 or COX-2 at concentrations up to 100 µM.1 Inhibition of MAGL hydrolysis of 2-arachidonoyl glycerol (2-AG) is associated with enhanced stress-induced analgesia and may represent a novel drug target in pain and stress management.5

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Technical Information
Formal Name
6-methyl-2-[(4-methylphenyl)amino]-1-benzoxazin-4-one
CAS Number
86672-58-4
Molecular Formula
C16H14N2O2
Formula Weight
266.3
Purity
>98%
Formulation
A crystalline solid
λmax
216, 247, 283, 348 nm
SMILES
Cc1ccc(cc1)Nc1nc2ccc(C)cc2c(=O)o1
InChI Code
InChI=1S/C16H14N2O2/c1-10-3-6-12(7-4-10)17-16-18-14-8-5-11(2)9-13(14)15(19)20-16/h3-9H,1-2H3,(H,17,18)
InChI Key
GFWNGVKCDGYFKG-UHFFFAOYSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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References & Product Citations
Product Description References

1. 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).

2. 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).

3. Vandevoorde, S., Jonsson, K.O., 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).

4. Tarzia, G., Antonietti, F., Duranti, A., et al. Identification of a bioactive impurity in a commercial sample of 6-methyl-2-p-tolylaminobenzo[d][1,3]oxazin-4-one (URB754) Ann. Chim. 97(9), 887-894 (2007).

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

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