102585-08-0

Basic information

• Product Name: 3-quinuclidinyl xanthene-9-carboxylate
• Synonyms: 3-quinuclidinyl xanthene-9-carboxylate;1-azabicyclo[2.2.2]oct-3-yl 9H-xanthene-9-carboxylate
• CAS NO: 102585-08-0
• Molecular Formula: C21H21 N O3
• Molecular Weight: 335.4
• Mol File: 102585-08-0.mol

Chemical Properties

• Boiling Point: 449.3°C at 760 mmHg
• Flash Point: 225.5°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 2.9E-08mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: 3-quinuclidinyl xanthene-9-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-quinuclidinyl xanthene-9-carboxylate(102585-08-0)
• EPA Substance Registry System: 3-quinuclidinyl xanthene-9-carboxylate(102585-08-0)

Safety Data

• Hazardous Substances Data: 102585-08-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H21NO3/c23-21(25-19-13-22-11-9-14(19)10-12-22)20-15-5-1-3-7-17(15)24-18-8-4-2-6-16(18)20/h1-8,14,19-20H,9-13H2

Upstream product

• 39497-06-8 9H-xanthene-9-carboxylic acid methyl ester 
• 3684-26-2 (S)-quinuclidin-3-ol 
• 82-07-5 xanthene-9-carboxylic acid 
• 25333-42-0 (R)-quinuclidin-3-ol 

Relevant articles and documents

NEW QUATERNIZED QUINUCLIDINE ESTERS

Compounds of formula (1) wherein the different substituents and/or radicals have the values defined in the claims. The invention also relates to a process for the preparation of said compounds, to pharmaceutical compositions comprising them, as well as to combinations of said compounds with other compounds which are active in the treatment of respiratory, urological or gastrointestinal disorders or diseases. Finally the invention also relates to the use of the compounds of formula (I) for the treatment of respiratory, urological or gastrointestinal disorders or diseases.

Affinity and Selectivity of the Optical Isomers of 3-Quinuclidinyl BenzAlate and Related Muscarinic Antagonists

All the optical isomers of the muscarinic antagonists 3-(1-azabicyclooctyl) α-hydroxy-α,α-diphenylacetate (3-quinuclidinyl benzilate, QNB, 1), 3-(1-azabicyclooctyl)xanthene-9-carboxylate (3-quinuclidinyl xanthene-9-carboxylate, QNX, 2), and 3-(1-azabicyclooctyl) α-hydroxy-α-phenylpropionate (3-quinuclidinyl atrolactate, QNA, 3) were prepared and studied in binding and functional assays.In all instances the esters of (R)-1-azabicyclooctan-3-ol (3-quinuclidinol) had greater affinity for the M1 and M2 subpopulations of muscarinic acetylcholine receptors (M-AChRs) than did their S counterparts.The enantiomers of QNB (1), QNX (2), and QNA (3) in which the alcoholic portion of the muscarinic anatagonists had the S absolute stereochemistry were more selective for the M1-AChRs.This selectivity was modulated by the nature and, in the case of QNA, the chirality of the acid portion.The most potent isomer in the series was (R)-QNB.In the QNA series the diastereoisomer with the absolute R configuration of the alcohol (a) and the R configuration of the acid (b) was the most potent in both binding and functional assays whereas (Sa,Rb)-QNA was the most selective for the M1 subtype of M-AChRs.In fact, the latter diastereomer was as potent and selective as pirenzepine for M1-AChRs.