LUPININE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H19NO.ClH
Molecular Weight	205.725
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ZKXVUMSVQBQBCR-BAUSSPIASA-N

InChI=1S/C10H19NO.ClH/c12-8-9-4-3-7-11-6-2-1-5-10(9)11;/h9-10,12H,1-8H2;1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Epiquinamide: a poison that wasn't from a frog that was.	2009 Feb 27	19245264
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 17:11:52 GMT 2023` Edited by `admin` on `Fri Dec 15 17:11:52 GMT 2023`
Record UNII	F9BHN6SHEW
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LUPININE HYDROCHLORIDE

Common Name

English

LUPININE L-FORM HYDROCHLORIDE [MI]

Common Name

English

(-)-LUPININE HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

LUPININE, HYDROCHLORIDE

Common Name

English

2H-QUINOLIZINE-1-METHANOL, OCTAHYDRO-, HYDROCHLORIDE, (1R-TRANS)-

Systematic Name

English

Code System Code Type Description

FDA UNII

F9BHN6SHEW