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MCHB-1

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
MCHB-1
Identifiers
  • 2-(4-ethoxybenzyl)-1-(cyclohexylmethyl)-N,N-diethyl-1H-benzo[d]imidazole-5-carboxamide
CAS Number
PubChemCID
ChemSpider
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 abenzimidazole derived drug which was researched as ananalgesic but never developed for medical use. It acts as a potentagonist of theCB2 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 adesigner drug, first being identified in Germany in December 2013.[3]

See also

[edit]

References

[edit]
  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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