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C003

Sigma-Aldrich

(R)-(−)-3-Quinuclidinyl benzilate

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Synonym(s):
(R)-(−)-QNB, (R)-(−)-Quinuclidinyl-α-hydroxydiphenylacetate
Empirical Formula (Hill Notation):
C21H23NO3
CAS Number:
62869-69-6
Molecular Weight:
337.41
MDL number:
MFCD00085375
UNSPSC Code:
12352005
PubChem Substance ID:
57653972
NACRES:
NA.22

form

solid

Quality Level

100

storage temp.

2-8°C

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

InChI key

HGMITUYOCPPQLE-IBGZPJMESA-N

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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)
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