123536-14-1

Basic information

• Product Name: (R)-3-Aminoquinuclidine dihydrochloride
• Synonyms: (R)-(+)-3-AMINOQUINUCLIDINE DIHYDROCHLORIDE;(R) 3-AMINOQUINUCLIDINE HYDROCHLORIDE;(3R)-QUINUCLIDIN-3-AMINE DIHYDROCHLORIDE;(R)-(+)-3-Aminoquinuclidine diHCl;(R)-1-AZABICYCLO[2,2,2]OCTAN-3-AMINE DIHYDROCHLORIDE;(R)-(+)-3-Aminoquinuclidine2HCl;1-azabicyclo[2,2,2]octan-3-amine,dihydrochloride,(R)-;(3R)-Quinuclidin-3-amine dihydrochloride 97%
• CAS NO: 123536-14-1
• Molecular Formula: C₇H₁₄N₂*2ClH
• Molecular Weight: 199.12
• Product Categories: Pharmaceutical material and intermeidates;INTERMEDIATESOFPALONOSETRONHYDROCHLORIDE;Amines;Ring Systems;Chiral Building Blocks;Heterocyclic Building Blocks;Quinuclidines
• Mol File: 123536-14-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 165.9 °C at 760 mmHg
• Flash Point: 51.1 °C
• Appearance: White to beige/Powder
• Density: 1.06g/cm3
• Vapor Pressure: 1.83mmHg at 25°C
• Refractive Index: 1.551
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly, Heated, Sonicated), Methanol (Slightly, Heated, Sonicated), Wat
• Stability: Hygroscopic
• CAS DataBase Reference: (R)-3-Aminoquinuclidine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-Aminoquinuclidine dihydrochloride(123536-14-1)
• EPA Substance Registry System: (R)-3-Aminoquinuclidine dihydrochloride(123536-14-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-R36/37/38
• Safety Statements: 26-38-36-S36-S26
• WGK Germany: 3
• Hazardous Substances Data: 123536-14-1(Hazardous Substances Data)

Usage

Description

(R)-3-Aminoquinuclidine dihydrochloride is a white to beige powdery compound that serves as a crucial intermediate in the pharmaceutical industry. It is predominantly utilized in the synthesis of various pharmaceuticals, particularly serotonin type 3 (5-HT3) receptor antagonists, which are potential new drugs for the treatment of irritable bowel syndrome (IBS).

Uses

1. Pharmaceutical Industry:
(R)-3-Aminoquinuclidine dihydrochloride is used as a key building block for the synthesis of pharmaceuticals. Its chiral nature allows for the creation of specific drug candidates with desired therapeutic properties.
2. Treatment of Irritable Bowel Syndrome (IBS):
In the medical field, (R)-3-Aminoquinuclidine dihydrochloride is used as a precursor in the development of serotonin type 3 (5-HT3) receptor antagonists. These antagonists are potential new drugs for the treatment of irritable bowel syndrome (IBS), a common gastrointestinal disorder characterized by abdominal pain, bloating, and changes in bowel habits.
3. Synthesis of Serotonin Type 3 (5-HT3) Receptor Antagonists:
(R)-3-Aminoquinuclidine dihydrochloride is used as a vital component in the preparation of 5-HT3 receptor antagonists. These antagonists play a significant role in managing the symptoms of IBS by blocking the action of serotonin on the 5-HT3 receptors, thereby reducing gastrointestinal discomfort and improving the quality of life for patients.

InChI:InChI=1/C7H14N2/c8-7-5-9-3-1-6(7)2-4-9/h6-7H,1-5,8H2/t7-/m0/s1

Upstream product

• 142999-65-3 N-<(3S)-3-quinuclidinyl> phthalimide 
• 134932-30-2 R-N-(Quinuclidinyl-3)-propionamide 
• 120570-06-1 N-((S)-1-phenylethyl)-3-quinuclidinimine 
• 1193-65-3 3-quinuclidinone hydrochloride 
• 3731-38-2 3-Quinuclidinone 
• 120577-33-5 (3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine 
• 120570-09-4 (3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine dihydrochloride 
• 134932-29-9 S-N-(quinuclidinyl-3)-propionamide 
• 1619-34-7 3-quinuclidinol 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 827-61-2 3-acetoxyquinuclidine 
• 59653-40-6 (+)-Aceclidine 
• 120570-06-1 N-((R)-1-phenylethyl)-3-quinuclidinimine 
• 142999-60-8 (3S)-3-<(R)-(1-phenyl)ethylamino>-quinuclidine 

Downstream Products

• 373357-49-4 (R)-(+)-(1-Aza-bicyclo[2.2.2]oct-3-yl)-carbamic acid benzyl ester 

Relevant articles and documents

Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl]benzamide and its 5-halogen-2-alkoxyl homologues

(S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [125I]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [125I]-MIZAC at 1800 Ci/mmol. Binding of [125I]-MIZAC in rat entorhinal cortex revealed a K(D) of 1.37 ± 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [125I]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [125I]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

Preparation of S-(-)- and R-(+)-N-(quinuclidinyl-3)-amide

Optical active forms of the carboxylic acid amines of 3-aminoquinuclidine of formula (I), and the preparation thereof. These can be hydrolysed to the optical active forms of 3-aminoquinuclidine.

Anxiolytic-R-n(1-azabicyclo[2.2.2]oct-3-yl) benzamides and thiobenzamides

Compounds of general formula I STR1 wherein: X represents oxygen or sulphur; each of R1 and R3 independently represents hydrogen or a C1 -C4 alkyl group; Ar represents: a phenyl ring optionally substituted by one, two or three C1 -C4 alkoxy groups and/or by one or two halogen atoms; a phenyl ring of the general formula STR2 wherein R2 represents halogen, 4,5-benzo, C1 -C8 alkoxy, C1 -C4 alkylcarbonyl or Am, wherein Am represents amino, methylamino or dimethylamino, R4 represents C1 -C8 alkyl, n is 1 or 2; or a pyrimidinyl moiety of the general formula STR3 wherein R5 is C1 -C4 alkyl; and their N-oxides and pharmaceutically acceptable salts are useful as anxiolytic agents. A preferred compound is R-(+)-4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide.