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MCHB-1

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Chemical compound Pharmaceutical compound
MCHB-1
Identifiers
IUPAC name
  • 2-(4-ethoxybenzyl)-1-(cyclohexylmethyl)-N,N-diethyl-1H-benzoimidazole-5-carboxamide
CAS Number
PubChem CID
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H37N3O2
Molar mass447.623 g·mol
3D model (JSmol)
SMILES
  • CCN(CC)C(=O)C1=CC2=C(C=C1)N(C(=N2)CC3=CC=C(C=C3)OCC)CC4CCCCC4
InChI
  • 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). It has been sold online as a designer drug, first being identified in Germany in December 2013.

See also

References

  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.


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