IMPERIALINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H43NO3
Molecular Weight	429.6352
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@]3([H])[C@@]([H])(CC(=O)[C@@]4([H])C[C@@H](O)CC[C@]34C)[C@]1([H])CC[C@]5([H])[C@@]2([H])CN6C[C@@H](C)CC[C@@]6([H])[C@@]5(C)O

InChI

InChIKey=IQDIERHFZVCNRZ-LRCDAWNTSA-N

InChI=1S/C27H43NO3/c1-15-4-7-25-27(3,31)21-6-5-17-18(20(21)14-28(25)13-15)11-22-19(17)12-24(30)23-10-16(29)8-9-26(22,23)2/h15-23,25,29,31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21+,22-,23+,25-,26+,27-/m0/s1

HIDE SMILES / InChI

Description
Sources: http://www.sciencedirect.com/science/article/pii/S0040403900938681 | https://www.ncbi.nlm.nih.gov/pubmed/27524867 | https://www.ncbi.nlm.nih.gov/pubmed/1448179 | https://www.ncbi.nlm.nih.gov/pubmed/17027747 | https://www.ncbi.nlm.nih.gov/pubmed/21958967 | https://www.ncbi.nlm.nih.gov/pubmed/26132855 | https://www.ncbi.nlm.nih.gov/pubmed/22101082 | https://www.ncbi.nlm.nih.gov/pubmed/28496003 | https://www.ncbi.nlm.nih.gov/pubmed/25935480

Imperialine is a steroidal alkaloid first isolated from the bulb of Fritillaria imperialis L. (Liliaceae). Bulbs of Fritillaria have been used in many Asian countries for a long time to treat pulmonary diseases, such as cough, expectoration, and asthma. Imperialine is one of the biologically active constituents in Fritillaria. It acts as a selective antagonist at muscarinic M2 receptors. It exerts antitussive, expectorant, and anti-inflammatory properties. In addition, imperialine demonstrated antineoplastic potential in vitro.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
inflammatory response 47 Target ID: GO:0006954 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26132855 \| https://www.ncbi.nlm.nih.gov/pubmed/27524867 \| https://www.ncbi.nlm.nih.gov/pubmed/21958967	Inhibitor 8297
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003	Activator 1430
autophagy 17 Target ID: GO:0006914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003 \| https://www.ncbi.nlm.nih.gov/pubmed/25935480	Activator 1430
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1448179 \| https://www.ncbi.nlm.nih.gov/pubmed/17027747	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27524867	Primary		Preclinical	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003 https://www.ncbi.nlm.nih.gov/pubmed/25935480	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacological investigation of imperialine--an alkaloid from Fritillaria imperialis Linn.	1965 Oct	5860837
Characterization of the interaction of the cervane alkaloid, imperialine, at muscarinic receptors in vitro.	1992 Aug	1448179
Selective antagonism activity of alkaloids from bulbs Fritillariae at muscarinic receptors: functional studies.	2006 Dec 3	17027747

Patents

Sample Use Guides

In Vivo Use Guide

Rats: 3.5 or 7 mg/kg

Route of Administration: Intragastric

In Vitro Use Guide

50-400 uM peiminine (imperialine) induces apoptosis and autophagy in HCT-116 cells

Name

Type

Language

IMPERIALINE

Common Name

English

SIPEIMINE

Common Name

English

CEVAN-6-ONE, 3,20-DIHYDROXY-, (3.BETA.,5.ALPHA.,17.BETA.)-

Systematic Name

English

KASHMIRINE

Common Name

English

NSC-282170

Code

English

Code System Code Type Description

EPA CompTox

DTXSID001031589