LUPININE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H19NO
Molecular Weight	169.264
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/556411 | https://www.ncbi.nlm.nih.gov/pubmed/624390

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

Primary Target	Pharmacology	Condition	Potency
Cholinesterase 14 Target ID: P06276 Gene ID: 590.0 Gene Symbol: BCHE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7405439	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.	2010-02-05	20038131
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.	2009-10-26	19857257
Epiquinamide: a poison that wasn't from a frog that was.	2009-02-27	19245264
Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.	2008-12-02	19040102
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	18476706
Cholinesterase hydrolysis of substituted lupinine benzoates.	2008-05-29	18505160
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	18205934
Phytochemical differences between Calia secundiflora (Leguminosae) growing at two sites in Mexico.	2006-05-30	16729569
[Synthesis of lupinine derivatives of flavonoids].	2005-10-26	16245698
Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.	2005-05-12	15876047
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].	2004-10-16	15481367
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	15224338
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.	2003-05-14	12741131
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.	2002-06	12031432
Indolizidine and quinolizidine alkaloids.	2001-10	11699884
2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine.	2001-03	11409323

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 19:33:52 GMT 2025` Edited by `admin` on `Mon Mar 31 19:33:52 GMT 2025`
Record UNII	33BAJ73U1F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-21723

Preferred Name

English

LUPININE

Common Name

English

(1R,9AR)-OCTAHYDRO-2H-QUINOLIZINE-1-METHANOL

Common Name

English

(-)-LUPININE

Common Name

English

L-LUPININE

Common Name

English

LUPININE [MI]

Common Name

English

Code System Code Type Description

MESH

C015971