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3-Quinuclidinyl thiochromane-4-carboxylate

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Chemical compound

Pharmaceutical compound

3-Quinuclidinyl thiochromane-4-carboxylate
Identifiers

IUPAC name 1-azabicyclo[2.2.2]octan-3-yl 3,4-dihydro-2H-1-benzothiopyran-4-carboxylate
CAS Number	112605-36-4
PubChemCID	13953381
ChemSpider	129322734
CompTox Dashboard(EPA)	DTXSID901336926
Chemical and physical data
Formula	C₁₇H₂₁NO₂S
Molar mass	303.42 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OC1CN2CCC1CC2)C1CCSc2ccccc21
InChI InChI=1S/C17H21NO2S/c19-17(20-15-11-18-8-5-12(15)6-9-18)14-7-10-21-16-4-2-1-3-13(14)16/h1-4,12,14-15H,5-11H2 Key:WKRAGTKCJCJQIR-UHFFFAOYSA-N

3-Quinuclidinyl thiochromane-4-carboxylate is a research compound which is the most potentmuscarinic antagonist known. Testsin vitro showed it to have a binding affinity over 2100 times more potent than3-quinuclidinyl benzilate (BZ) with an apparentassociation constant (K_A) of 2.47picomolar (pM).^[1]^[2]

^Cohen VI, Gibson RE, Reba RC (October 1987). "Synthesis and structure-activity relationships of new muscarinic antagonists".Journal of Pharmaceutical Sciences.76 (10):848–50.Bibcode:1987JPhmS..76..848C.doi:10.1002/jps.2600761020.PMID 3430351.
^Ball JC (2015)."Dual Use Research of Concern: Derivatives of 3-Quinuclidinyl Benzilate".Military Medical Science Letters.84 (1):2–41.doi:10.31482/mmsl.2015.001.