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

[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

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 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Indolizidine and quinolizidine alkaloids.	2001 Oct	11699884
Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.	2002 Jun	12031432
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.	2003 Jan-Feb	12741131
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	15224338
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].	2004 Jul-Aug	15481367
Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.	2005 May 12	15876047
[Synthesis of lupinine derivatives of flavonoids].	2005 Sep-Oct	16245698
Cholinesterase hydrolysis of substituted lupinine benzoates.	2008 Mar-Apr	18505160
Epiquinamide: a poison that wasn't from a frog that was.	2009 Feb 27	19245264
Comparative analysis of medicinal plants used in traditional medicine in Italy and Tunisia.	2009 Oct 26	19857257
Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.	2010 Feb 5	20038131

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 `Fri Dec 15 19:09:33 GMT 2023` Edited by `admin` on `Fri Dec 15 19:09:33 GMT 2023`
Record UNII	33BAJ73U1F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUPININE

Common Name

English

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

Common Name

English

(-)-LUPININE

Common Name

English

L-LUPININE

Common Name

English

NSC-21723

Code

English

LUPININE [MI]

Common Name

English

Code System Code Type Description

MESH

C015971