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Chemical compound
MCHB-1
2-(4-ethoxybenzyl)-1-(cyclohexylmethyl)-N,N-diethyl-1H-benzo[d]imidazole-5-carboxamide
CAS Number PubChem CID UNII ChEMBL CompTox Dashboard (EPA ) Formula C 28 H 37 N 3 O 2 Molar mass 447.623 g·mol−1 3D model (JSmol )
CCN(CC)C(=O)C1=CC2=C(C=C1)N(C(=N2)CC3=CC=C(C=C3)OCC)CC4CCCCC4
InChI=1S/C28H37N3O2/c1-4-30(5-2)28(32)23-14-17-26-25(19-23)29-27(31(26)20-22-10-8-7-9-11-22)18-21-12-15-24(16-13-21)33-6-3/h12-17,19,22H,4-11,18,20H2,1-3H3
Key:WRVZBXHTUOPQJS-UHFFFAOYSA-N
MCHB-1 is a benzimidazole derived drug which was researched as an analgesic but never developed for medical use. It acts as a potent agonist of the CB2 receptor , with an EC50 of 0.52nM at CB2 , and ~30x selectivity over CB1 (Ki of 110nM at CB1 vs 3.7nM at CB2 ).[1] [2] It has been sold online as a designer drug , first being identified in Germany in December 2013.[3]
See also
References
^ Pagé D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, et al. (July 2008). "Novel benzimidazole derivatives as selective CB2 agonists". Bioorganic & Medicinal Chemistry Letters . 18 (13): 3695–700. doi :10.1016/j.bmcl.2008.05.073 . PMID 18522867 .
^ Yu XH, Cao CQ, Martino G, Puma C, Morinville A, St-Onge S, et al. (November 2010). "A peripherally restricted cannabinoid receptor agonist produces robust anti-nociceptive effects in rodent models of inflammatory and neuropathic pain". Pain . 151 (2): 337–44. doi :10.1016/j.pain.2010.07.019 . PMID 20696525 . S2CID 27731273 .
^ Westphal F, Sönnichsen FD, Knecht S, Auwärter V, Huppertz L (April 2015). "Two thiazolylindoles and a benzimidazole: novel compounds on the designer drug market with potential cannabinoid receptor activity". Forensic Science International . 249 : 133–47. doi :10.1016/j.forsciint.2015.01.014 . PMID 25698514 .
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