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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

[H][C@]12CCCCN1CCC[C@H]2CO

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

Molecular Formula C10H19NO
Molecular Weight 169.264
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine.
2001 Mar
Indolizidine and quinolizidine alkaloids.
2001 Oct
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.
2002 Jun
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.
2003 Jan-Feb
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 Jul 5
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
2004 Jul-Aug
Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.
2005 May 12
[Synthesis of lupinine derivatives of flavonoids].
2005 Sep-Oct
Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico.
2006 Mar-Apr
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 Jan 18
A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.
2008 Jun 19
Cholinesterase hydrolysis of substituted lupinine benzoates.
2008 Mar-Apr
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.
2008 Sep-Oct
Epiquinamide: a poison that wasn't from a frog that was.
2009 Feb 27
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.
2009 Oct 26
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.
2010 Feb 5
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 Sat Dec 16 08:00:45 GMT 2023
Edited
by admin
on Sat Dec 16 08:00:45 GMT 2023
Record UNII
F74RAC8A5Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LUPININE, (±)-
Common Name English
2H-QUINOLIZINE-1-METHANOL, OCTAHYDRO-, (1R-TRANS)-(±)-
Systematic Name English
(±)-LUPININE
Common 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 Sat Dec 16 08:00:45 GMT 2023 , Edited by admin on Sat Dec 16 08:00:45 GMT 2023
PRIMARY
MERCK INDEX
m6939
Created by admin on Sat Dec 16 08:00:45 GMT 2023 , Edited by admin on Sat Dec 16 08:00:45 GMT 2023
PRIMARY Merck Index
FDA UNII
F74RAC8A5Q
Created by admin on Sat Dec 16 08:00:45 GMT 2023 , Edited by admin on Sat Dec 16 08:00:45 GMT 2023
PRIMARY
PUBCHEM
91461
Created by admin on Sat Dec 16 08:00:45 GMT 2023 , Edited by admin on Sat Dec 16 08:00:45 GMT 2023
PRIMARY