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|ImageSize=200px |
|ImageSize=200px |
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|IUPACName=Cyclohexyl [1,1'-biphenyl]-3-ylcarbamate |
|IUPACName=Cyclohexyl [1,1'-biphenyl]-3-ylcarbamate |
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|OtherNames=[1, |
|OtherNames=[1,1'-Biphenyl]-3-yl-carbamic acid, cyclohexyl ester |
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|Section1= {{Chembox Identifiers |
|Section1= {{Chembox Identifiers |
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| CASNo=565460-15-3 |
| CASNo=565460-15-3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21) |
| StdInChI=1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21) |
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| SMILES = O=C(OC1CCCCC1) |
| SMILES = O=C(OC1CCCCC1)Nc1cccc(c1)c1ccccc1 |
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}} |
}} |
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|Section2= {{Chembox Properties |
|Section2= {{Chembox Properties |
Revision as of 16:33, 8 November 2012
Names | |
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IUPAC name
Cyclohexyl [1,1'-biphenyl]-3-ylcarbamate
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Other names
[1,1'-Biphenyl]-3-yl-carbamic acid, cyclohexyl ester
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Identifiers | |
3D model (JSmol)
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ChEMBL | |
ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C19H21NO2 | |
Molar mass | 295.382 g·mol−1 |
Appearance | Crystalline solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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URB602 ([1,1'-biphenyl]-3-yl-carbamic acid, cyclohexyl ester) is a compound that has been found to inhibit hydrolysis of monoacyl glycerol compounds, such as 2-arachidonoylglycerol (2-AG) and 2-oleoylglycerol (2-OG). It was first described in 2003.[1] A study performed in 2005 found that the compound had specificity for metabolizing 2-AG over anandamide (another cannabinoid ligand) in rat brain presumably by inhibiting the enzyme monoacylglycerol lipase (MAGL), which is the primary metabolic enzyme of 2-AG.[2] However, subsequent studies have shown that URB602 lacks specificity for MAGL inhibition in vitro.[3]
References
- ^ Tarzia, G; Duranti, A; Tontini, A; Piersanti, G; Mor, M; Rivara, S; Plazzi, PV; Park, C; Kathuria, S (2003). "Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors". Journal of Medical Chemistry. 46 (12): 2352–60. doi:10.1021/jm021119g. PMID 12773040.
- ^ Hohmann, Andrea G.; Suplita, Richard L.; Bolton, Nathan M.; Neely, Mark H.; Fegley, Darren; Mangieri, Regina; Krey, Jocelyn F.; Michael Walker, J.; Holmes, Philip V. (2005). "An endocannabinoid mechanism for stress-induced analgesia". Nature. 435 (7045): 1108–12. Bibcode:2005Natur.435.1108H. doi:10.1038/nature03658. PMID 15973410.
- ^ Vandevoorde, S; Jonsson, K-O; Labar, G; Persson, E; Lambert, D M; Fowler, C J (2007). "Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysisin vitro". British Journal of Pharmacology. 150 (2): 186–91. doi:10.1038/sj.bjp.0706971. PMC 2042901. PMID 17143303.