6530-09-2

Basic information

• Product Name: 3-Aminoquinuclidine dihydrochloride
• Synonyms: LABOTEST-BB LT00012585;3-AMINOQUINUCLIDINE DIHYDROCHLORIDE;3-AMINO-1-AZABICYCLO[2.2.2]OCTANE DIHYDROCHLORIDE;3-AMINOCHINUCLIDIN DIHYDROCHLORIDE;QUINUCLIDIN-3-AMINE DIHYDROCHLORIDE;TIMTEC-BB SBB000378;1-Azabicyclo[2.2.2]octan-3-amine, Dihydrochloride;3-Aminoquiuclidine diHCl
• CAS NO: 6530-09-2
• Molecular Formula: C₇H₁₄N₂*2ClH
• Molecular Weight: 199.12
• EINECS: 229-424-6
• Product Categories: Amines;Ring Systems;Building Blocks;Heterocyclic Building Blocks;Quinuclidines;Heterocycles;Intermediates
• Mol File: 6530-09-2.mol

Chemical Properties

• Melting Point: 321-323 °C (dec.)(lit.)
• Boiling Point: 165.9 °C at 760 mmHg
• Flash Point: 51.1 °C
• Appearance: White to almost white/Powder
• Density: 1.06 g/cm3
• Vapor Pressure: 1.83mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Methanol, Water
• CAS DataBase Reference: 3-Aminoquinuclidine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminoquinuclidine dihydrochloride(6530-09-2)
• EPA Substance Registry System: 3-Aminoquinuclidine dihydrochloride(6530-09-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: VD4590000
• Hazardous Substances Data: 6530-09-2(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white powder

Uses

An intermediate in the preparation of Azasetron.

InChI:InChI:1S/C7H14N2.2ClH/c8-7-5-9-3-1-6(7)2-4-9;;/h6-7H,1-5,8H2;2*1H

Upstream product

• 6238-15-9 3-acetamido-1-azabicyclo<2.2.2>octane 
• 142999-60-8 (3S)-3-<(R)-(1-phenyl)ethylamino>-quinuclidine 
• 120577-33-5 (3R)-3-<(S)-(1-phenyl)ethylamino>-quinuclidine 
• 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 
• 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 

Downstream Products

• 142999-61-9 (S)-N-(R)-1-Aza-bicyclo[2.2.2]oct-3-yl-3,3,3-trifluoro-2-methoxy-2-phenyl-propionamide 
• 340682-26-0 (R)-N-(1-azabicyclo[2.2.2]oct-3-yl)(E-3-phenylpropenamide) 
• 1403993-24-7 (R)-4-phenyl-1-(quinuclidin-3-yl)-1H-1,2,3-triazol-5-amine 

Relevant articles and documents

Kinetic Self-Sorting of Dynamic Covalent Catalysts with Systemic Feedback Regulation

Constructing small molecule systems that mimic the functionality exhibited in biological reaction networks is a key objective of systems chemistry. Herein, we report the development of a dynamic catalytic system where the catalyst activity is modulated through a dynamic covalent bond. By connecting a thermodynamically controlled rearrangement process to resolution under kinetic control, the catalyst system underwent kinetic self-sorting, resulting in amplification of a more reactive catalyst while establishing a catalytic feedback mechanism. The dynamic catalyst system furthermore responded to catalytic events by self-perturbation to regulate its own activity, which in the case of upregulation gave rise to systemic autocatalytic behavior.

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.

Improved preparation of (R) and (S)-3-aminoquinuclidine dihydrochloride

An improved procedure for the synthesis of either (R) or (S)-3-aminoquinuclidine was developed. Key intermediate imine 2 was made in a one pot process using lithium oxide as the base and molecular sieves.

Synthesis of tritium labelled (R) and (S)-3-aminoquinuclidine: A ubiquitous component of serotonin receptor ligands, part I

(R) and (S)-3-aminoquinuclidines-3H with the specific activity of 35 Ci/mmol were prepared. Reduction of enamide 2 with carrier free tritium gas over RhCODCl dimer, (2S, 3S) Chiraphos in methanol gave racemic amide 9c. Hydrolysis followed by resolution of the enantiomers with (R)-methyl benzyl isocyanate gave (R) and (S)-3-aminoquinuclidine-3H 10c-S and 10c-R. The enantiopurity purity of both isomers was >99.5%.

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.

Indole derivatives and drugs

The object of the invention is to provide a novel compound having serotonin antagonist activity. The invention is directed to an indolecarboxamide derivative of the following general formula [I] and a serotonin antagonist composition comprising the same derivative as an active ingredient. STR1 (wherein R1 is a lower alkyl and R2 is hydrogen, a halogen, a lower alkyl or a lower alkoxy.) The compound of the invention is effective as a gastrointestinal motor activity regulator, antimigraine, antipsychotic or antianxiety drug. The compound is also effective as a therapeutic drug for dementia or orthostatic hypotension.

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.

Enantiomers of absolute configuration S of amide derivatives of 3-aminoquinuclidine, the process for preparing them and their application in therapy

Enantiomer of absolute configuration S of formula: STR1 where: X=O or S; and Ar denotes a: * phenyl ring substituted with one, two or three C1 -C4 alkoxy groups; * phenyl ring substituted at the 2-position with a OCH3 group and at the 5-position with a halogen atom or a lower alkylcarbonyl group; * phenyl ring substituted at the 2-position with OCH3, at the 4-position with NH2 or alkylcarbonyl-NH and at the 5-position with a halogen; * 3-fluoro-2-methoxyphenyl group; * 5-pyrimidinyl group substituted at the 2-position with NH2 and in the 4-position with alkoxy or phenyloxy. These compounds are useful as medicinal products having activity in respect of gastric movements and antiemetic activity.

Synthesis of (R) and (S)-3-aminoquinuclidine from 3-quinuclidinone and (S) and (R)-1-phenethylamine

The synthesis of (R) and (S)-3-amino quinuclidine, an important building block for the synthesis of chiral 5-HT3 serotonin receptor antagonists, is described. The key reaction is the reduction by NaBH4 of the imine prepared from the 3-quinuclidinone and chiral (S) or (R)-1-phenethylamine.

Method of treating or preventing schizophrenia and/or psychosis using S-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 antischizophrenic and/or antipsychotic agents. A preferred compound is S(-)-4-amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-5-chloro-2-methoxybenzamide.