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URB602

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URB602
Names
Preferred IUPAC name Cyclohexyl (-3-yl)carbamate
Other names -3-yl-carbamic acid, cyclohexyl ester
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=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)Key: HHVUFQYJOSFTEH-UHFFFAOYSA-N
SMILES
  • O=C(OC1CCCCC1)Nc1cccc(c1)c1ccccc1
Properties
Chemical formula C19H21NO2
Molar mass 295.382 g·mol
Appearance Crystalline solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

URB602 (-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. 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. However, subsequent studies have shown that URB602 lacks specificity for MAGL inhibition in vitro.

References

  1. Tarzia, G; Duranti, A; Tontini, A; Piersanti, G; Mor, M; Rivara, S; Plazzi, PV; Park, C; et al. (2003). "Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors". Journal of Medicinal Chemistry. 46 (12): 2352–60. doi:10.1021/jm021119g. PMID 12773040. S2CID 30528443.
  2. Hohmann, Andrea G.; Suplita, Richard L.; Bolton, Nathan M.; Neely, Mark H.; Fegley, Darren; Mangieri, Regina; Krey, Jocelyn F.; Michael Walker, J.; et al. (2005). "An endocannabinoid mechanism for stress-induced analgesia" (PDF). Nature. 435 (7045): 1108–12. Bibcode:2005Natur.435.1108H. doi:10.1038/nature03658. PMID 15973410. S2CID 4339948.
  3. 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.
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