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Details

Stereochemistry ACHIRAL
Molecular Formula C7H13N
Molecular Weight 111.1848
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINUCLIDINE

SMILES

C1CN2CCC1CC2

InChI

InChIKey=SBYHFKPVCBCYGV-UHFFFAOYSA-N
InChI=1S/C7H13N/c1-4-8-5-2-7(1)3-6-8/h7H,1-6H2

HIDE SMILES / InChI

Molecular Formula C7H13N
Molecular Weight 111.1848
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Quinuclidine is a bicyclic amine. It is used in organic synthesis. Quinuclidine is a highly potent catalyst for aldimine transaminations. Quinuclidine derivatives possess antihistamine properties and might be used for the treatment of various allergic diseases. They are demonstrated anti-inflammatory and other clinically important properties.

Originator

Sources: DOI: 10.1002/cber.19090420115

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Atmospheric heterogeneous stereochemistry.
2009-09-30
Organocatalytic activity of cinchona alkaloids: which nitrogen is more nucleophilic?
2009-09-18
Tertiary amine and N-heterocyclic carbene coordinated haloalanes--synthesis, structure, and application.
2009-09-14
Fluorinated quinine alkaloids: synthesis, X-ray structure analysis and antimalarial parasite chemotherapy.
2009-08-03
New, improved treatments for Chagas disease: from the R&D pipeline to the patients.
2009-07-07
Discovery of novel 1-azoniabicyclo[2.2.2]octane muscarinic acetylcholine receptor antagonists.
2009-04-23
Structure and rheology of cationic molecular hydrogels of quinuclidine grafted bile salts. Influence of the ionic strength and counter-ion type.
2009-04-09
Efficient N-arylation/dealkylation of electron deficient heteroaryl chlorides and bicyclic tertiary amines under microwave irradiation.
2009-03-24
1-Pyridine- and 1-quinuclidine-1-boraadamantane as models for derivatives of 1-borabicyclo[2.2.2]octane. Experimental and theoretical evaluation of the B-N fragment as a polar isosteric substitution for the C-C group in liquid crystal compounds.
2009-02-20
Management of postoperative nausea and vomiting: focus on palonosetron.
2009-02
Fluorescence quenching of CdSe quantum dots by tertiary amines and their surface binding effect.
2009-01
Sterol Biosynthesis Pathway as Target for Anti-trypanosomatid Drugs.
2009
Multiple pharmacophores for the selective activation of nicotinic alpha7-type acetylcholine receptors.
2008-12
Use of molecular electrostatic potential for quantitative assessment of inductive effect.
2008-11-21
Polyepichlorhydrin membranes for alkaline fuel cells: sorption and conduction properties.
2008-10-02
Interaction energies and dynamics of acid-base pairs isolated in cavitands.
2008-09-05
The crystal structure of halofantrine-ferriprotoporphyrin IX and the mechanism of action of arylmethanol antimalarials.
2008-08
Application of the PM6 method to modeling the solid state.
2008-06
Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare.
2008-03
Quinuclidine complex with alpha-cyclodextrin: a diffusion and 13C NMR relaxation study.
2008-03
alpha7 nicotinic acetylcholine receptor agonist properties of tilorone and related tricyclic analogues.
2008-03
Mixed-ligand metal-organic frameworks with large pores: gas sorption properties and single-crystal-to-single-crystal transformation on guest exchange.
2008
Huge deuterated effect on permittivity in a metal-organic framework.
2008
Effectiveness of low-dose doxycycline (LDD) on clinical symptoms of Sjögren's syndrome: a randomized, double-blind, placebo controlled cross-over study.
2007-12-31
Synthesis and characterization of new nitrogen-donor-stabilized N-silylphosphoranimine cations.
2007-11-12
Adducts of rhodium(II) tetraacetate with some nitrogenous organic ligands: application of natural abundance 15N and 13C CPMAS NMR spectroscopy.
2007-10
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.
2007-08-29
Metabolism, pharmacokinetics, and excretion of a nonpeptidic substance P receptor antagonist, ezlopitant, in normal healthy male volunteers: characterization of polar metabolites by chemical derivatization with dansyl chloride.
2007-07
Molecular structures of free quinuclidine and its adducts with metal trihydrides, MH3 (M=B, Al or Ga), studied by gas-phase electron diffraction, X-ray diffraction and quantum chemical calculations.
2007-05-07
Quinuclidines as selective agonists for alpha-7 nicotinic acetylcholine receptors.
2007-03-15
The nature of the chemical bond in linear three-body systems: from i3- to mixed chalcogen/halogen and trichalcogen moieties.
2007
Investigation of the stability of the M-H-B bond in borane sigma complexes [M(CO)5(eta1-BH2R.L)] and [CpMn(CO)2(eta1-BH2R.L)] (M=Cr, W; L=tertiary amine or phosphine): substituent and Lewis base effects.
2007
A synthetic mimic of protein inner space: buried polar interactions in a deep water-soluble host.
2006-12-06
Zona pellucida from fertilised human oocytes induces a voltage-dependent calcium influx and the acrosome reaction in spermatozoa, but cannot be penetrated by sperm.
2006-12-05
Synthetic studies on quinine: quinuclidine construction via a ketone enolate regio- and diastereoselective Pd-mediated allylic alkylation.
2006-08-31
Method for enantiomeric purity of a quinuclidine candidate drug by capillary electrophoresis.
2006-08
RP-HPLC method with fluorescence detection for determination of small quantities of triamcinolone in plasma in presence of endogenous steroids after derivatization with 9-anthroyl nitrile; pharmacokinetic studies.
2006-07-24
Antiproliferative activities of two novel quinuclidine inhibitors against Toxoplasma gondii tachyzoites in vitro.
2006-07
A generalized two-point H-bonding model for catalytic stereoselective hydrogenation of activated ketones on chirally modified platinum.
2006-06-14
Pyridinium, imidazolium and quinuclidinium compounds: toxicity and antidotal effects against the nerve agents Tabun and Soman.
2006-06
Perturbation of adsorbed CO by amine derivatives coadsorbed on the gamma-Al2O3 surface: FTIR and first principles studies.
2006-03-16
m-Calpain is required for preimplantation embryonic development in mice.
2006-01-24
Potent anti-muscarinic activity in a novel series of quinuclidine derivatives.
2006-01-15
Structure and reactivity of trans-bis[2-(2-chloroethyl)pyridine]palladium chloride (1). A study on the elimination reaction of 1 and 2-(2-chloroethyl)pyridine induced by quinuclidine in acetonitrile.
2005-12-23
Rate-limiting proton-transfer in the sigma-adduct forming reactions of 1,3,5-trinitrobenzene and 4-nitrobenzofuroxan with substituted anilines in dimethyl sulfoxide.
2005-11-07
High affinity ligands for the alpha7 nicotinic receptor that show no cross-reactivity with the 5-HT3 receptor.
2005-11-01
Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists.
2005-10-20
A deep cavitand provides a structured environment for the Menschutkin reaction.
2005-08-17
Synthesis and photophysical properties of models for twisted PRODAN and dimethylaminonaphthonitrile.
2005-02-24
Structure-property relationship in py-hexahydrocinchonidine diastereomers: ab initio and NMR study.
2005-02-10
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:18:25 GMT 2025
Edited
by admin
on Mon Mar 31 21:18:25 GMT 2025
Record UNII
XFX99FC5VI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-168431
Preferred Name English
QUINUCLIDINE
MI  
Systematic Name English
QUINUCLIDINE [MI]
Common Name English
1,4-ETHYLENEPIPERIDINE
Common Name English
1,4-ETHANOPIPERIDINE
Systematic Name English
1-AZABICYCLO(2.2.2)OCTANE
Systematic Name English
Code System Code Type Description
CAS
100-76-5
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
WIKIPEDIA
QUINUCLIDINE
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
FDA UNII
XFX99FC5VI
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
MERCK INDEX
m9468
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY Merck Index
PUBCHEM
7527
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
EPA CompTox
DTXSID2057607
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-887-1
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
CHEBI
38420
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY
NSC
168431
Created by admin on Mon Mar 31 21:18:25 GMT 2025 , Edited by admin on Mon Mar 31 21:18:25 GMT 2025
PRIMARY