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MCHB-1

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MCHB-1
Identifiers
  • 2-(4-ethoxybenzyl)-1-(cyclohexylmethyl)-N,N-diethyl-1H-benzo[d]imidazole-5-carboxamide
CAS Number
PubChem CID
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]

See also

References

  1. ^ Pagé D, Balaux E, Boisvert L, et al. Novel benzimidazole derivatives as selective CB2 agonists. Bioorganic & Medicinal Chemistry Letters 2008; 18(13): 3695-3700. PMID 18522867 doi:10.1016/j.bmcl.2008.05.073
  2. ^ Yu XH, Cao CQ, Martino G, et al. A peripherally restricted cannabinoid receptor agonist produces robust anti-nociceptive effects in rodent models of inflammatory and neuropathic pain. Pain 2010; 151(2): 337-344. doi:10.1016/j.pain.2010.07.019
  3. ^ Westphal F, Sönnichsen FD, Knecht S, Auwärter V, Huppertz L. Two thiazolylindoles and a benzimidazole: Novel compounds on the designer drug market with potential cannabinoid receptor activity. Forensic Sci. Int. 2015; 249: 133–147. doi:10.1016/j.forsciint.2015.01.014