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Details

Stereochemistry RACEMIC
Molecular Formula C10H19NO
Molecular Weight 169.264
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUPININE, (±)-

SMILES

OC[C@@H]1CCCN2CCCC[C@H]12

InChI

InChIKey=HDVAWXXJVMJBAR-VHSXEESVSA-N
InChI=1S/C10H19NO/c12-8-9-4-3-7-11-6-2-1-5-10(9)11/h9-10,12H,1-8H2/t9-,10+/m0/s1

HIDE SMILES / InChI
Lupinine is a bitter tasting quinolizidine alkaloid present in Lupinus species of the Family Fabaceae. It has been shown to lower the locomotion excitation brought on by ethanol anesthesia in mice. Lupinine has also shown some ability to inhibit human and rabbit cholinesterases.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P06276
Gene ID: 590.0
Gene Symbol: BCHE
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.
2010-02-05
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.
2009-10-26
Epiquinamide: a poison that wasn't from a frog that was.
2009-02-27
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.
2008-12-02
A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.
2008-06-19
Cholinesterase hydrolysis of substituted lupinine benzoates.
2008-05-29
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
Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico.
2006-05-30
[Synthesis of lupinine derivatives of flavonoids].
2005-10-26
Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.
2005-05-12
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
2004-10-16
Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives.
2004-07-05
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.
2003-05-14
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.
2002-06
Indolizidine and quinolizidine alkaloids.
2001-10
2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine.
2001-03
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
LUPININE, (±)-
Common Name English
(±)-LUPININE
Preferred Name English
2H-QUINOLIZINE-1-METHANOL, OCTAHYDRO-, (1R-TRANS)-(±)-
Systematic Name English
LUPININE DL-FORM [MI]
Common Name English
2H-QUINOLIZINE-1-METHANOL, OCTAHYDRO-, (1R,9AR)-REL-
Systematic Name English
Code System Code Type Description
CAS
10248-30-3
Created by admin on Mon Mar 31 21:49:15 GMT 2025 , Edited by admin on Mon Mar 31 21:49:15 GMT 2025
PRIMARY
MERCK INDEX
m6939
Created by admin on Mon Mar 31 21:49:15 GMT 2025 , Edited by admin on Mon Mar 31 21:49:15 GMT 2025
PRIMARY Merck Index
FDA UNII
F74RAC8A5Q
Created by admin on Mon Mar 31 21:49:15 GMT 2025 , Edited by admin on Mon Mar 31 21:49:15 GMT 2025
PRIMARY