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Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[u... |
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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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'''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.<ref name=Tarzia2003>{{cite journal | last1 = Tarzia | first1 = G | last2 = Duranti | first2 = A | last3 = Tontini | first3 = A | last4 = Piersanti | first4 = G | last5 = Mor | first5 = M | last6 = Rivara | first6 = S | last7 = Plazzi | first7 = PV | last8 = Park | first8 = C | last9 = Kathuria | first9 = S | title = Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors | journal = Journal of |
'''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.<ref name=Tarzia2003>{{cite journal | last1 = Tarzia | first1 = G | last2 = Duranti | first2 = A | last3 = Tontini | first3 = A | last4 = Piersanti | first4 = G | last5 = Mor | first5 = M | last6 = Rivara | first6 = S | last7 = Plazzi | first7 = PV | last8 = Park | first8 = C | last9 = Kathuria | first9 = S | last10 = Piomelli | first10 = Daniele | title = Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors | journal = Journal of Medicinal Chemistry | volume = 46 | issue = 12 | pages = 2352–60 | year = 2003 | pmid = 12773040 | doi = 10.1021/jm021119g| s2cid = 30528443 | display-authors = 8 | url = http://www.escholarship.org/uc/item/7sb397f0 }}</ref> 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.<ref name=Hohmann2005>{{cite journal | last1 = Hohmann | first1 = Andrea G. | last2 = Suplita | first2 = Richard L. | last3 = Bolton | first3 = Nathan M. | last4 = Neely | first4 = Mark H. | last5 = Fegley | first5 = Darren | last6 = Mangieri | first6 = Regina | last7 = Krey | first7 = Jocelyn F. | last8 = Michael Walker | first8 = J. | last9 = Holmes | first9 = Philip V. | last10 = Crystal | first10 = Jonathon D. | last11 = Duranti | first11 = Andrea | last12 = Tontini | first12 = Andrea | last13 = Mor | first13 = Marco | last14 = Tarzia | first14 = Giorgio | last15 = Piomelli | first15 = Daniele | title = An endocannabinoid mechanism for stress-induced analgesia | journal = Nature | volume = 435 | issue = 7045 | pages = 1108–12 | year = 2005 | pmid = 15973410 | doi = 10.1038/nature03658 | bibcode=2005Natur.435.1108H| s2cid = 4339948 | display-authors = 8 | url = https://cloudfront.escholarship.org/dist/prd/content/qt4gn3454w/qt4gn3454w.pdf }}</ref> However, subsequent studies have shown that URB602 lacks specificity for MAGL inhibition ''in vitro''.<ref name=Vandevoorde2007>{{cite journal | last1 = Vandevoorde | first1 = S | last2 = Jonsson | first2 = K-O | last3 = Labar | first3 = G | last4 = Persson | first4 = E | last5 = Lambert | first5 = D M | last6 = Fowler | first6 = C J | title = Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysisin vitro | journal = British Journal of Pharmacology | volume = 150 | issue = 2 | pages = 186–91 | year = 2007 | pmid = 17143303 | pmc = 2042901 | doi = 10.1038/sj.bjp.0706971}}</ref> |
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==References== |
==References== |
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{{reflist}} |
{{reflist}} |
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{{Cannabinoid-stub}} |
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[[Category:Cannabinoids]] |
[[Category:Cannabinoids]] |
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[[Category:Carbamates]] |
[[Category:Carbamates]] |
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[[Category:Biphenyls]] |
[[Category:Biphenyls]] |
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[[Category:Cyclohexyl compounds]] |
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Latest revision as of 02:50, 2 December 2022
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| Names | |
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| Preferred IUPAC name
Cyclohexyl ([1,1′-biphenyl]-3-yl)carbamate | |
| 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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| UNII | |
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[edit]
- ^ 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.
- ^ 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.
- ^ 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.