QUINOLIZIDINE

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 Search

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

Title	Date	PubMed
Dimeric sesquiterpene thioalkaloids with potent immunosuppressive activity from the rhizome of Nuphar pumilum: structural requirements of nuphar alkaloids for immunosuppressive activity.	2001 Apr	11354659
Antiproliferative activity and interactions with cell-cycle related proteins of the organotin compound triethyltin(IV)lupinylsulfide hydrochloride.	2001 Mar 14	11248220
The biosynthesis of beta-carboline and quinolizidine alkaloids of Alangium lamarckii.	2002 Aug	12150812
Analysis of proprietary Chinese medicines for the presence of toxic ingredients by LC/MS/MS.	2002 Aug 22	12151076
Indolizidine and quinolizidine alkaloids.	2002 Dec	12521266
Seed chemistry of Sophora chrysophylla (mamane) in relation to diet of specialist avian seed predator Loxioides bailleui (palila) in Hawaii.	2002 Jul	12199503
Highly enantioenriched tetrahydropyridines from chiral organosilanes: application to the synthesis of quinolizidine alkaloid (-)-217A.	2003 Jan 22	12526650
Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived delta-lactam.	2003 Mar 7	12608811
Bioassay-guided isolation of epiquinamide, a novel quinolizidine alkaloid and nicotinic agonist from an Ecuadoran poison frog, Epipedobates tricolor.	2003 Oct	14575435
Amidopalladation of alkoxyallenes applied in the synthesis of an enantiopure 1-ethylquinolizidine frog alkaloid.	2004 Apr 7	15053587
Quinolizidine alkaloids isolated from Lupinus species enhance insulin secretion.	2004 Nov 3	15507230
Alkaloids indolizidine 235B', quinolizidine 1-epi-207I, and the tricyclic 205B are potent and selective noncompetitive inhibitors of nicotinic acetylcholine receptors.	2004 Oct	15258256
A straightforward and versatile synthetic approach to 1-azabicyclic alkaloids.	2004 Oct 15	15471460
A sensitive and specific HPLC-MS method for the determination of sophoridine, sophocarpine and matrine in rabbit plasma.	2005 Aug	15997382
Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants.	2005 Jan	15659437
Determination of quinolizidine alkaloids in Sophora tonkinensis by HPCE.	2005 Jul-Aug	16042151
Indolizidine and quinolizidine alkaloids.	2005 Oct	16193159
Quinolizidine alkaloids and phomopsins in lupin seeds and lupin containing food.	2006 Apr 21	16359686
Effects of oxymatrine on proliferation and apoptosis in human hepatoma cells.	2006 Mar 1	16458489
(+)-12alpha-Hydroxysophocarpine, a new quinolizidine alkaloid and related anti-HBV alkaloids from Sophora flavescens.	2006 Mar 1	16364643
Cytisus scoparius link--a natural antioxidant.	2006 Mar 16	16542432
Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico.	2006 Mar-Apr	16729569
Determination of quinolizidine alkaloids in Sophora flavescens and its preparation using capillary electrophoresis.	2006 May	16167304
Phloem alkaloid tolerance allows feeding on resistant Lupinus angustifolius by the aphid Myzus persicae.	2006 Sep	16906361
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 Apr 11	17291705
Desymmetrization of 7-azabicycloalkenes by tandem olefin metathesis for the preparation of natural product scaffolds.	2007 Dec 18	18088413
[Stereochemistry, syntheses and biological activity of lupine alkaloids--from studies on the leguminous plants growing mainly in Japan].	2007 Oct	17917418
Indolizidines and quinolizidines: natural products and beyond.	2007 Sep 26	17897459
Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols.	2008 Aug	18499644
Combining two-directional synthesis and tandem reactions, part 11: second generation syntheses of (+/-)-hippodamine and (+/-)-epi-hippodamine.	2008 Jan 17	18201377
Microemulsion electrokinetic chromatography coupling with field amplified sample injection and electroosmotic flow suppressant for analysis of some quinolizidine alkaloids.	2008 Jul 11	18533172
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 Oct	18539842

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:42:18 GMT 2023` Edited by `admin` on `Fri Dec 15 19:42:18 GMT 2023`
Record UNII	S6O58HOW33
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUINOLIZIDINE

Common Name

English

NORLUPINANE

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