U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of IMPERIALINE

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
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

Sources: K. Fragner. Ber. dtsch. chem. Ges., 21 (1888), p. 3284.
Curator's Comment: reference retrieved from http://www.sciencedirect.com/science/article/pii/S0040403900938681

Approval Year

PubMed

PubMed

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

Patents

Sample Use Guides

Rats: 3.5 or 7 mg/kg
Route of Administration: Intragastric
50-400 uM peiminine (imperialine) induces apoptosis and autophagy in HCT-116 cells
Name Type Language
IMPERIALINE
MI  
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
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
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WIKIPEDIA
Imperialin
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
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PUBCHEM
442977
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
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CAS
61825-98-7
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
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FDA UNII
JKN43410XZ
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
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MERCK INDEX
m6238
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
PRIMARY Merck Index
RXCUI
1860087
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
PRIMARY
NSC
282170
Created by admin on Sat Dec 16 08:07:08 GMT 2023 , Edited by admin on Sat Dec 16 08:07:08 GMT 2023
PRIMARY