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

C[C@H]1CC[C@@H]2N(C1)C[C@H]3[C@@H]4C[C@H]5[C@@H](CC(=O)[C@H]6C[C@@H](O)CC[C@]56C)[C@@H]4CC[C@H]3[C@]2(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

Molecular Formula	C27H43NO3
Molecular Weight	429.6352
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8504
apoptotic process 51 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003	Activator 1447
autophagy 17 Target ID: GO:0006914 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28496003 \| https://www.ncbi.nlm.nih.gov/pubmed/25935480	Activator 1447
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 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 175 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27524867	Primary		Preclinical	Unknown Approved Use Unknown
Colorectal cancer 102 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
Selective antagonism activity of alkaloids from bulbs Fritillariae at muscarinic receptors: functional studies.	2006-12-03	17027747
Characterization of the interaction of the cervane alkaloid, imperialine, at muscarinic receptors in vitro.	1992-08	1448179
Pharmacological investigation of imperialine--an alkaloid from Fritillaria imperialis Linn.	1965-10	5860837

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:53:41 GMT 2025` Edited by `admin` on `Mon Mar 31 21:53:41 GMT 2025`
Record UNII	JKN43410XZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMPERIALINE

Common Name

English

NSC-282170

Preferred 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

Code System Code Type Description

EPA CompTox

DTXSID001031589