URB754 4539781 215553605 2008-05-28T18:38:42Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{chembox new | Name = URB754 | ImageFile = URB754.svg | ImageSize = 250 | IUPACName = | SystematicName = | OtherNames = | Section1 = {{Chembox Identifiers | Abbreviations = | CASNo = 86672-58-4 | EINECS = | EINECSCASNO = | PubChem = | SMILES = | InChI = | RTECS = | MeSHName = | ChEBI = | KEGG = | ATCCode_prefix = | ATCCode_suffix = | ATC_Supplemental =}} | Section2 = {{Chembox Properties | Formula = | MolarMass = | Appearance = | Density = | MeltingPt = | Melting_notes = | BoilingPt = | Boiling_notes = | Solubility = | SolubleOther = | Solvent = | LogP = | VaporPressure = | HenryConstant = | AtmosphericOHRateConstant = | pKa = | pKb = }} | Section3 = {{Chembox Structure | CrystalStruct = | Coordination = | MolShape = }} | Section4 = {{Chembox Thermochemistry | DeltaHf = | DeltaHc = | Entropy = | HeatCapacity = }} | Section5 = {{Chembox Pharmacology | AdminRoutes = | Bioavail = | Metabolism = | HalfLife = | ProteinBound = | Excretion = | Legal_status = | Legal_US = | Legal_UK = | Legal_AU = | Legal_CA = | PregCat = | PregCat_AU = | PregCat_US = }} | Section6 = {{Chembox Explosive | ShockSens = | FrictionSens = | ExplosiveV = | REFactor = }} | Section7 = {{Chembox Hazards | ExternalMSDS = | EUClass = | EUIndex = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-O = | RPhrases = | SPhrases = | RSPhrases = | FlashPt = | Autoignition = | ExploLimits = | LD50 = | PEL = }} | Section8 = {{Chembox Related | OtherAnions = | OtherCations = | OtherFunctn = | Function = | OtherCpds = }} }} '''URB754''' was originally reported to be a potent, noncompetitive inhibitor of [[monoacylglycerol lipase]].<ref name="pmid16116451">{{cite journal |author=Makara JK, Mor M, Fegley D, Szabó SI, Kathuria S, Astarita G, Duranti A, Tontini A, Tarzia G, Rivara S, Freund TF, Piomelli D |title=Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus |journal=Nat. Neurosci. |volume=8 |issue=9 |pages=1139–41 |year=2005 |pmid=16116451 |doi=10.1038/nn1521}}</ref> However, recent studies have shown that URB754 failed to inhibit recombinant MGL, and brain [[FAAH]] activity was also resistant to URB754.<ref>{{cite journal |author=Saario SM, Palomäki V, Lehtonen M, Nevalainen T, Järvinen T, Laitinen JT |title=URB754 has no effect on the hydrolysis or signaling capacity of 2-AG in the rat brain |journal=Chem. Biol. |volume=13 |issue=8 |pages=811–4 |year=2006 |pmid=16931330 |doi=10.1016/j.chembiol.2006.07.008}}</ref> Some controversy in the field remains regarding the use of this compound. <!-- Whoever wants to read the following, can go to the 2-AG article. Otherwise, rewrite it better [[2-Arachidonoylglycerol]] (2-AG) is an endogenous agonist of the central cannabinoid receptor (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] [[Monoacylglycerol lipase]] (MGL) hydrolyzes 2-AG to [[arachidonic acid]] and glycerol, thereby terminating its biological actions.[4] --> ==References== <references/> <!-- # Stella, N., Schweitzer, P., Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388, 773-778 (1997). # 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). # 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). # 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). # Makara, J.K., Mor, M., Fegley, D., et al. Selective inhibition of 2-AG hydrolysis enhances endocannabinoid signaling in hippocampus. Nature Neuroscience 8(9), 1139-1141 (2005). # Hohmann, A.G., Suplita, R.L., Bolton, N.M., et al. An endocannabinoid mechanism for stress-induced analgesia. Nature 435, 1108-1112 (2005). --> {{Cannabinoids}} {{pharma-stub}}