MCHB-1

MCHB-1
Identifiers
  • 2-(4-ethoxybenzyl)-1-(cyclohexylmethyl)-N,N-diethyl-1H-benzo[d]imidazole-5-carboxamide
CAS Number
PubChem CID
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H37N3O2
Molar mass447.623 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]

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.