Imperialin

Names
IUPAC name

3β,20β-Dihydroxy-5α,17β-cevan-6-one

Systematic IUPAC name

(3S,4aS,6aS,6bS,8aR,9S,9aS,12S,15aS,15bR,16aS,16bR)-3,9-Dihydroxy-9,12,16b-trimethyldocosahydrobenzo[4,5]indeno[1,2-h]pyrido[1,2-b]isoquinolin-5(1H)-one

Other names

Imperialine; Sipeimine; Kashmirine; (3β,5α,17β)-3,20-Dihydroxycevan-6-one

Identifiers

CAS Number

* 61825-98-7 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1623724

ChemSpider |

* 391280

PubChem CID

* 442977

UNII |

* JKN43410XZ Y

InChI

* 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

Key: IQDIERHFZVCNRZ-LRCDAWNTSA-N

SMILES

* C[C@H]1CC[C@H]2[C@@]([C@@H]3CC[C@@H]4[C@H]([C@@H]3CN2C1)C[C@H]5[C@H]4CC(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O)C)(C)O

Properties

Chemical formula

| C27H43NO3
Molar mass | 429.645 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Imperialin (imperialine or peiminine[1]) is an alkaloid found in the bulbs of species of the genus Fritillaria, where it occurs to the extent of 0.1 - 2.0%. In humans it may cause spasms, vomiting, hypotension and cardiac arrest.

## Management

Inducing vomiting and administering activated charcoal. Spasmolytics may be required.[2]

## References

1. ↑ "Peiminine". PubChem. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=442977&loc=ec_rcs. Retrieved 24 January 2014.
2. ↑ Reichl, Franz-Xaver; Leonard Ritter (2010). Illustrated Handbook of Toxicology. Thieme. ISBN 313149591X. https://books.google.com/books?id=9hHACrSGgyIC. Retrieved 18 March 2014.

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*[CID]: Compound ID