C003

(R)-(−)-3-Quinuclidinyl benzilate

• 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

Properties

• form: solid
• 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)

Description

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331
• Precautionary Statements: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves