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Merck
CN

C003

(R)-(−)-3-Quinuclidinyl benzilate

Synonym(s):

(R)-(−)-QNB, (R)-(−)-Quinuclidinyl-α-hydroxydiphenylacetate

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About This Item

Empirical Formula (Hill Notation):
C21H23NO3
CAS Number:
62869-69-6
Molecular Weight:
337.41
NACRES:
NA.22
PubChem Substance ID:
57653972
UNSPSC Code:
12352005
MDL number:
MFCD00085375
Form:
solid

Key Documents

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InChI key

HGMITUYOCPPQLE-IBGZPJMESA-N

SMILES string

OC(C(=O)O[C@H]1CN2CCC1CC2)(c3ccccc3)c4ccccc4

InChI

1S/C21H23NO3/c23-20(25-19-15-22-13-11-16(19)12-14-22)21(24,17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-10,16,19,24H,11-15H2/t19-/m0/s1

form

solid

storage temp.

2-8°C

Quality Level

100

Gene Information

rat ... Chrm1(25229), Chrm2(81645), Chrm3(24260)

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Application

(R)-(-)-3-Quinuclidinyl benzilate can be used as a reactant for the synthesis of quaternary ammonium derivatives of (3R)-quinuclidinol esters as potential muscarinic M3 antagonists. It can also be employed in the preparation of potent muscarinic cholinergic antagonist (R)-[N-methyl-3H]quinuclidinyl benzilate methiodide by alkylation with methyl iodide.
  • Pharmacological agent used as muscarinic M3 antagonist for the inhaled treatment of chronic obstructive pulmonary disease (COPD)

Biochem/physiol Actions

Nonselective muscarinic acetylcholine receptor antagonist. More potent enantiomer of QNB.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
097H4727

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A convenient synthesis of the muscarinic cholinergic antagonist (R)-[N-methyl-3H] quinuclidinyl benzilate methiodide
Filer CN and Seguin RJ
Journal of Labelled Compounds & Radiopharmaceuticals, 62(9), 604-607 (2019)
Measurement of total acid number (TAN) and TAN boiling point distribution in petroleum products by electrospray ionization mass spectrometry
Q Kuangnan et al.
Analytical Chemistry, 80(3), 849-855 (2008)
Qiaoying Lv et al.
Cancer letters, 442, 137-147 (2018-11-14)
Continuous estrogen signaling is thought to be the main mechanism causing endometrial cancer (EC). Studies have demonstrated that CD163+ macrophages could promote the development of estrogen-dependent EC, but the mechanisms involved remain unclear. We found that CD163+ macrophages were the

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