MCHB-1

MCHB-1
Identifiers
	IUPAC name 2-(4-ethoxybenzyl)-1-(cyclohexylmethyl)-N,N-diethyl-1H-benzo[d]imidazole-5-carboxamide;
CAS Number	1046140-32-2;
PubChem CID	44561533;
UNII	W8QNY2T4YC;
ChEMBL	ChEMBL470965;
CompTox Dashboard (EPA)	DTXSID501336524 ;
Chemical and physical data
Formula	C28H37N3O2
Molar mass	447.623 g·mol−1
3D model (JSmol)	Interactive image;
	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).^[1]^[2] It has been sold online as a designer drug, first being identified in Germany in December 2013.^[3]

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.

[pmid18522867-1] 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.

[pmid20696525-2] 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.

[pmid25698514-3] 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.

[1]

[2]

[3]

See also

References