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Details

Stereochemistry ACHIRAL
Molecular Formula C9H17N
Molecular Weight 139.238
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINOLIZIDINE

SMILES

C1CCN2CCCCC2C1

InChI

InChIKey=LJPZHJUSICYOIX-UHFFFAOYSA-N
InChI=1S/C9H17N/c1-3-7-10-8-4-2-6-9(10)5-1/h9H,1-8H2

HIDE SMILES / InChI

Molecular Formula C9H17N
Molecular Weight 139.238
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Actions of quinolizidine alkaloids on Periplaneta americana nicotinic acetylcholine receptors.
2008-12
The effect of body condition on serum concentrations of two teratogenic alkaloids (anagyrine and ammodendrine) from lupines (Lupinus species) that cause crooked calf disease.
2008-10
Pharmacokinetic study of matrine, oxymatrine and oxysophocarpine in rat plasma after oral administration of Sophora flavescens Ait. extract by liquid chromatography tandem mass spectrometry.
2008-08-05
Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.
2008-08
Microemulsion electrokinetic chromatography coupling with field amplified sample injection and electroosmotic flow suppressant for analysis of some quinolizidine alkaloids.
2008-07-11
Quinolizidine alkaloids in seeds of lupin genotypes of different origins.
2008-05-28
Evaluation of total quinolizidine alkaloids content in lupin flours, lupin-based ingredients, and foods.
2008-04
Alkaloids from Daphniphyllum oldhami.
2008-04
Palladium(II)-catalyzed direct arylation of enaminones using organotrifluoroborates.
2008-03-26
Analysis of quinolizidine alkaloids in Sophora flavescens Ait. by capillary electrophoresis with tris(2,2'-bipyridyl) ruthenium (II)-based electrochemiluminescence detection.
2008-03-15
Efficient synthesis of (+)-1,8,8a-tri-epi-swainsonine, (+)-1,2-di-epi-lentiginosine, (+)-9a-epi-homocastanospermine and (-)-9-deoxy-9a-epi-homocastanospermine from a D-glucose-derived aziridine carboxylate, and study of their glycosidase inhibitory activities.
2008-02-21
Indolizidine and quinolizidine alkaloids.
2008-02
Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(-)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(-)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol.
2008-01-18
Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.
2008-01-17
Influence of plant secondary metabolites on in vitro oxidation of methyl ferulate with cell wall peroxidases from lupine apoplast.
2008
Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds.
2007-12-18
Synthesis of densely functionalized enantiopure indolizidines by ring-closing metathesis (RCM) of hydroxylamines from carbohydrate-derived nitrones.
2007-12-12
Synthesis of poison-frog alkaloids 233A, 235U, and 251AA and their inhibitory effects on neuronal nicotinic acetylcholine receptors.
2007-11-01
A convenient allylsilane-N-acyliminium route toward indolizidine and quinolizidine alkaloids.
2007-10-02
[Stereochemistry, syntheses and biological activity of lupine alkaloids--from studies on the leguminous plants growing mainly in Japan].
2007-10
Indolizidines and quinolizidines: natural products and beyond.
2007-09-26
Vascular pharmacology of mokuboito (mu-fang-yi-tang) and its constituents on the smooth muscle and the endothelium in rat aorta.
2007-09
Induction of apoptosis by alkaloids, non-protein amino acids, and cardiac glycosides in human promyelotic HL-60 cells.
2007-08-22
Hypoglycaemic effect of quinolizidine alkaloids--lupanine and 2-thionosparteine on non-diabetic and streptozotocin-induced diabetic rats.
2007-06-22
NACE-ESI-MS combined with on-line concentration for high-sensitivity analysis of quinolizidine alkaloids.
2007-05
An approach to develop binary chromatographic fingerprints of the total alkaloids from Caulophyllum robustum by high performance liquid chromatography/diode array detector and gas chromatography/mass spectrometry.
2007-04-11
Supercritical fluid extraction of quinolizidine alkaloids from Sophora flavescens Ait. and purification by high-speed counter-current chromatography.
2007-03-23
Pd-catalysed [3 + 3] annelations in the stereoselective synthesis of indolizidines.
2007-02-08
Indolizidine and quinolizidine alkaloids.
2007-02
Synthesis, transport and accumulation of quinolizidine alkaloids in Lupinus albus L. and L. angustifolius L.
2007
Synthesis and pharmacological evaluation of novel octahydro-1H-pyrido[1,2-a]pyrazine as mu-opioid receptor antagonists.
2006-12-14
Elucidation of the bioactive conformation of the N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine class of mu-opioid receptor antagonists.
2006-12-14
Neuronal damage and changes in the expression of muscarinic acetylcholine receptor subtypes in the neonatal rat cerebral cortical upon exposure to sparteine, a quinolizidine alkaloid.
2006-10
Phloem alkaloid tolerance allows feeding on resistant Lupinus angustifolius by the aphid Myzus persicae.
2006-09
Chemotaxonomy of Portuguese Ulex: quinolizidine alkaloids as taxonomical markers.
2006-09
Total synthesis of clavepictines A and B and pictamine.
2006-07-20
Quinolizidine alkaloids with anti-HBV activity from Sophora tonkinensis.
2006-07
Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico.
2006-05-30
Determination of quinolizidine alkaloids in Sophora flavescens and its preparation using capillary electrophoresis.
2006-05
Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food.
2006-04-21
Cytisus scoparius link--a natural antioxidant.
2006-03-16
Effects of oxymatrine on proliferation and apoptosis in human hepatoma cells.
2006-03-01
(+)-12alpha-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens.
2006-03-01
Indolizidine and quinolizidine alkaloids.
2005-10
Histological evaluation of brain damage caused by crude quinolizidine alkaloid extracts from lupines.
2005-10
4-Aminoquinoline quinolizidinyl- and quinolizidinylalkyl-derivatives with antimalarial activity.
2005-09-15
Total synthesis of (+)-epiquinamide.
2005-09-01
A sensitive and specific HPLC-MS method for the determination of sophoridine, sophocarpine and matrine in rabbit plasma.
2005-08
A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry.
2005-07-27
Determination of quinolizidine alkaloids in Sophora tonkinensis by HPCE.
2005-07-27
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:54:09 GMT 2025
Edited
by admin
on Mon Mar 31 19:54:09 GMT 2025
Record UNII
S6O58HOW33
Record Status Validated (UNII)
Record Version
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Name Type Language
NORLUPINANE
Preferred Name English
QUINOLIZIDINE
Common Name English
2H-QUINOLIZINE, OCTAHYDRO-
Systematic Name English
1-AZABICYCLO(4.4.0)DECANE
Systematic Name English
QUINOLIZINE, OCTAHYDRO-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
QUINOLIZIDINE
Created by admin on Mon Mar 31 19:54:09 GMT 2025 , Edited by admin on Mon Mar 31 19:54:09 GMT 2025
PRIMARY
PUBCHEM
119036
Created by admin on Mon Mar 31 19:54:09 GMT 2025 , Edited by admin on Mon Mar 31 19:54:09 GMT 2025
PRIMARY
EPA CompTox
DTXSID90964203
Created by admin on Mon Mar 31 19:54:09 GMT 2025 , Edited by admin on Mon Mar 31 19:54:09 GMT 2025
PRIMARY
FDA UNII
S6O58HOW33
Created by admin on Mon Mar 31 19:54:09 GMT 2025 , Edited by admin on Mon Mar 31 19:54:09 GMT 2025
PRIMARY
CHEBI
46751
Created by admin on Mon Mar 31 19:54:09 GMT 2025 , Edited by admin on Mon Mar 31 19:54:09 GMT 2025
PRIMARY
CAS
493-10-7
Created by admin on Mon Mar 31 19:54:09 GMT 2025 , Edited by admin on Mon Mar 31 19:54:09 GMT 2025
PRIMARY
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