6581-06-2

Basic information

• Product Name: 3-Quinuclidinyl benzilate
• Synonyms: 1-Azabicyclo(2.2.2)octan-3-ol, benzilate;1-azabicyclo(2.2.2)octan-3-ol,benzilate;1-Azabicyclo[2.2.2]oct-3-yl hydroxy(diphenyl)acetate;3-(2,2-diphenyl-2-hydroxyethanoyloxy)-quinuclidine;3-Chinuclidylbenzilate;3-Hydroxyquinuclidine benzilate;3-Oxyquinuclidine benzilate;3-Quinuclidinol benzilate
• CAS NO: 6581-06-2
• Molecular Formula: C₂₁H₂₃NO₃
• Molecular Weight: 337.41
• EINECS: 233-250-6
• Mol File: 6581-06-2.mol

Chemical Properties

• Melting Point: 164.5°C
• Boiling Point: 473.72°C (rough estimate)
• Flash Point: 219.3oC
• Appearance: white/powder
• Density: 1.1644 (rough estimate)
• Vapor Pressure: 1.75E-08mmHg at 25°C
• Refractive Index: 1.5614 (estimate)
• Storage Temp.: 2-8°C
• Solubility: chloroform: but decomposes within 24 hrssoluble
• PKA: 11.28±0.29(Predicted)
• CAS DataBase Reference: 3-Quinuclidinyl benzilate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinuclidinyl benzilate(6581-06-2)
• EPA Substance Registry System: 3-Quinuclidinyl benzilate(6581-06-2)

Safety Data

• Hazard Codes: Xn,T+
• Statements: 22-26
• Safety Statements: 28-36/37-45
• WGK Germany: 3
• RTECS: DD4638000
• Hazardous Substances Data: 6581-06-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Warfare:
3-Quinuclidinyl benzilate (BZ) is used as a nonlethal chemical warfare agent that causes incapacitating effects and severe hallucinations. The US Army intended to use BZ in critical situations such as special operations, incapacitating adversaries during raids, and overcoming fortified field positions.
Used in Medical Applications:
3-Quinuclidinyl benzilate (BZ) is used as a muscarinic receptor antagonist in medical settings, helping to counteract the effects of excessive acetylcholine in the nervous system.

Environmental Fate

BZ acts by blocking the action of acetylcholine on the central and peripheral nervous systems. It is a tertiary amine and crosses the blood–brain barrier. BZ on acute exposure increases both heart and respiratory rates, dilates the pupils, and causes paralysis of the eye muscles necessary for near focusing. It also causes dry mouth and skin, elevates body temperature, impairs coordination, and causes flushing of the skin, hallucinations, stupor, forgetfulness, and confusion.Within 15 min to 4 h following exposure, the principal effects are dizziness, involuntary muscle movements, near vision difficulty, and total incapacitation. From 6 to 10 h after exposure, the effects are psychotropic and full recovery is expected after 4 days. The peripheral nervous system effects are considered as understimulation of the end organs. This decreased stimulation of eccrine and apocrine sweat glands in the skin results in dry skin and a dry mouth, and is considered ‘dry as a bone.’ The reduction in the ability to dispel heat by evaporative cooling decreases sweating, and the compensatory cutaneous vasodilation causes the skin to become warm or ‘hot as a hare’ and ‘red as a beet.’ This is similar to the atropine flush. The decreased heat loss also results in an increased core temperature.

Toxicity evaluation

QNB-BZ or Agent 15 has been tested on different surfaces by the US Army Medical Research Institute of Chemical Defense and the overall conclusion was that QNB-BZ persists as a parent molecule for an extended period of time reaching 72 h4.

InChI:InChI=1/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

Upstream product

• 1619-34-7 3-quinuclidinol 
• 76-89-1 methyl benzilate 
• 76-93-7 Benzilic acid 
• 3731-38-2 3-Quinuclidinone 
• 1838-39-7 ethyl N-ethoxycarbonylmethyl-4-piperidinecarboxylate 
• 695-88-5 3-methylquinuclidine 
• 1193-65-3 3-quinuclidinone hydrochloride 

Downstream Products

• 101481-83-8 1-Butyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-86-1 1-Heptyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-87-2 3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-octyl-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-84-9 3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-pentyl-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-88-3 3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-nonyl-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101504-49-8 1-Decyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-81-6 1-Ethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-82-7 3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-propyl-1-azonia-bicyclo[2.2.2]octane; iodide 
• 101481-85-0 1-Hexyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane; iodide 
• 71861-83-1 3-(2-hydroxy-2,2-diphenylacetoxy)-1-methylquinuclidin-1-ium iodide 
• 81381-93-3 IQNB 
• 346727-55-7 C₂₁⁽¹¹⁾CH₂₆NO₃⁽¹⁺⁾*I^(1-) 
• 76-93-7 Benzilic acid 
• 1619-34-7 3-quinuclidinol 

Relevant articles and documents

Identification of mepenzolate derivatives with long-acting bronchodilatory activity

The standard treatment for chronic obstructive pulmonary disease is a combination of anti-inflammatory drugs and bronchodilators. We recently found that mepenzolate bromide (MP), an antagonist for human muscarinic M3 receptor (hM3R), has both anti-inflammatory and short-acting bronchodilatory activities. To obtain MP derivatives with longer-lasting bronchodilatory activity, we synthesized hybrid compounds based on MP and two other muscarinic antagonists with long-acting bronchodilatory activity glycopyrronium bromide (GC) and aclidinium bromide (AD). Of these three synthesized hybrid compounds (MP-GC, GC-MP, MP-AD) and MP, MP-AD showed the highest affinity for hM3R and had the longest lasting bronchodilatory activity, which was equivalent to that of GC and AD. Both MP-GC and MP-AD exhibited an anti-inflammatory effect equivalent to that of MP, whereas, in line with GC and AD, GC-MP did not show this effect. We also confirmed that administration of MP-AD suppressed elastase-induced pulmonary emphysema in a mouse model. These findings provide important information about the structure-activity relationship of MP for both bronchodilatory and anti-inflammatory activities.

QUINUCLIDINE DERIVATIVE

Provided is a novel therapeutic agent for chronic obstructive pulmonary disease. Provided are a quinuclidine derivative and a medicament comprising the quinuclidine derivative. wherein R1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, or a haloalkoxy group; Y represents —C(C═O)—O—, —CH2—, or —CH2O—; m represents an integer of 1 to 5; Z represents an oxygen atom or a sulfur atom; l represents a number of 0 or 1; n represents an integer of 0 to 4; X? represents an anion; and a substituent of a quinuclidine ring represents a 1,3-bond, or 1,4-bond, provided that when m is 3, l is 1, and n is 0, R1 represents a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, or a haloalkoxy group.

NOVEL COMPOUNDS AS ANTI-TUBERCULAR AGENTS

The present invention relates to novel compounds of formula (1): The present invention also discloses compounds of formula (1) along with other pharmaceutical acceptable excipients and use of the compounds as anti-tubercular agents.