3-Quinuclidinyl thiochromane-4-carboxylate

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
PubChem CID	13953381
CompTox Dashboard (EPA)	DTXSID901336926 Edit this at Wikidata
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 potent muscarinic antagonist known. Tests in vitro showed it to have a binding affinity over 2100 times more potent than 3-quinuclidinyl benzilate with a K_i of 2.47 picomolars (pM).^[1]^[2]

It displays non-competitive inverse agonism at all muscarinic receptor subtypes and is irreversibly bound due to covalent binding; duration has been reported to be about 50 days from one exposure. Biological half-life is under 1 minute yet cannot be detected in blood due to reducing the constitutive activity at 100% of all mAChR' in the human organism (IA = -70%).^[1]

References

[edit ]

^ ^a ^b 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. 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 .

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Sulfur mustards	Levinstein mustard (EA-229) T Q CEES
Nitrogen mustards	HN1 HN2 HN3 TL-301
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Nerve agents

G-agents	Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin
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Carbamates	Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10)
Other	Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI
Precursors	Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG