Imperialine
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    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H558129

CAS#: 61825-98-7

Description: Imperialine is a compound in the traditional Chinese medicine chuanbeimu (Bulbus Fritillariae Cirrhosae) that has been used as antitussive/expectorant.


Chemical Structure

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Imperialine
CAS# 61825-98-7

Theoretical Analysis

Hodoodo Cat#: H558129
Name: Imperialine
CAS#: 61825-98-7
Chemical Formula: C27H43NO3
Exact Mass: 429.32
Molecular Weight: 429.645
Elemental Analysis: C, 75.48; H, 10.09; N, 3.26; O, 11.17

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 650 2 Weeks
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Synonym: Kashmirine; Sipeimine;

IUPAC/Chemical Name: Cevan-6-one, 3,20-dihydroxy-, (3-beta,5-alpha,17-beta)-

InChi Key: IQDIERHFZVCNRZ-LRCDAWNTSA-N

InChi Code: 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

SMILES Code: [H][C@]12C[C@@H](O)CC[C@]1(C)[C@@]3([H])C[C@@]4([H])[C@]5([H])CN6C[C@@H](C)CC[C@]([H])6[C@@](C)(O)[C@@]([H])5CC[C@]([H])4[C@]3([H])CC2=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 429.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Lin Q, Ling LQ, Guo L, Gong T, Sun X, Zhang ZR. Intestinal absorption characteristics of imperialine: in vitro and in situ assessments. Acta Pharmacol Sin. 2015 Jul;36(7):863-73. doi: 10.1038/aps.2015.27. Epub 2015 Jun 8. PubMed PMID: 26051111; PubMed Central PMCID: PMC4648119.

2: Lin Q, Fu Y, Li J, Qu M, Deng L, Gong T, Zhang Z. A (polyvinyl caprolactam-polyvinyl acetate-polyethylene glycol graft copolymer)-dispersed sustained-release tablet for imperialine to simultaneously prolong the drug release and improve the oral bioavailability. Eur J Pharm Sci. 2015 Nov 15;79:44-52. doi: 10.1016/j.ejps.2015.08.018. Epub 2015 Sep 5. PubMed PMID: 26349052.

3: Wu K, Mo C, Xiao H, Jiang Y, Ye B, Wang S. Imperialine and Verticinone from Bulbs of Fritillaria wabuensis Inhibit Pro-inflammatory Mediators in LPS-stimulated RAW 264.7 Macrophages. Planta Med. 2015 Jul;81(10):821-9. doi: 10.1055/s-0035-1546170. Epub 2015 Jul 1. PubMed PMID: 26132855.

4: Pan BF, Su X, Hu B, Yang N, Chen Q, Wu W. Fusarium redolens 6WBY3, an endophytic fungus isolated from Fritillaria unibracteata var. wabuensis, produces peimisine and imperialine-3β-D-glucoside. Fitoterapia. 2015 Jun;103:213-21. doi: 10.1016/j.fitote.2015.04.006. Epub 2015 Apr 11. PubMed PMID: 25869849.

5: Lin Q, Zhang Q, Song X, Gong T, Sun X, Zhang Z. Novel LC-MS/MS method for analyzing imperialine in rat plasma: development, validation, and application to pharmacokinetics. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Nov 1;938:51-9. doi: 10.1016/j.jchromb.2013.08.033. Epub 2013 Sep 1. PubMed PMID: 24055750.

6: Wang D, Du Q, Li H, Wang S. The Isosteroid Alkaloid Imperialine from Bulbs of Fritillaria cirrhosa Mitigates Pulmonary Functional and Structural Impairment and Suppresses Inflammatory Response in a COPD-Like Rat Model. Mediators Inflamm. 2016;2016:4192483. doi: 10.1155/2016/4192483. Epub 2016 Jul 20. PubMed PMID: 27524867; PubMed Central PMCID: PMC4971319.

7: Eglen RM, Harris GC, Cox H, Sullivan AO, Stefanich E, Whiting RL. Characterization of the interaction of the cervane alkaloid, imperialine, at muscarinic receptors in vitro. Naunyn Schmiedebergs Arch Pharmacol. 1992 Aug;346(2):144-51. PubMed PMID: 1448179.

8: Li P, Zeng LJ, Li SL, Lin G. The extraction of imperialine and imperialine-3 beta-glucoside from Fritillaria pallidiflora Schrenk and quantitative determination by HPLC-evaporative light scattering detection. Phytochem Anal. 2002 May-Jun;13(3):158-61. PubMed PMID: 12099106.

9: Chan SW, Li SL, Lin G, Li P. Pharmacokinetic study and determination of imperialine, the major bioactive component in antitussive Fritillaria cirrhosa, in rat by high-performance liquid chromatography coupled with evaporative light-scattering detector. Anal Biochem. 2000 Oct 1;285(1):172-5. PubMed PMID: 10998280.

10: Li SL, Li P, Zheng LJ. [Determination of imperialine and imperialine-3 beta-D-glucoside in bulbs of Fritillaria pallidiflora by HPLC-ELSD]. Yao Xue Xue Bao. 2001 Apr;36(4):300-2. Chinese. PubMed PMID: 12580061.

11: Atta-ur-Rahman, Choudhary MI, Farooq A, Anjum S, Baumgold J, Sener B. Structure-activity relationships of imperialine derivatives and their anticholinergic activity. Planta Med. 1998 Mar;64(2):172-4. PubMed PMID: 9525109.

12: Mir GN, Ghatak BJ. Pharmacological investigation of imperialine--an alkaloid from Fritillaria imperialis Linn. Indian J Exp Biol. 1965 Oct;3(4):249-52. PubMed PMID: 5860837.

13: Akbulut H, Gören Z, Iskender E, Eraslan A, Ozdemir O, Oktay S. Subtypes of muscarinic receptors in rat duodenum: a comparison with rabbit vas deferens, rat atria, guinea-pig ileum and gallbladder by using imperialine. Gen Pharmacol. 1999 Apr;32(4):505-11. PubMed PMID: 10323493.

14: Wang D, Wang S, Chen X, Xu X, Zhu J, Nie L, Long X. Antitussive, expectorant and anti-inflammatory activities of four alkaloids isolated from Bulbus of Fritillaria wabuensis. J Ethnopharmacol. 2012 Jan 6;139(1):189-93. doi: 10.1016/j.jep.2011.10.036. Epub 2011 Nov 10. PubMed PMID: 22101082.

15: Lin BQ, Ji H, Li P, Jiang Y, Fang W. Selective antagonism activity of alkaloids from bulbs Fritillariae at muscarinic receptors: functional studies. Eur J Pharmacol. 2006 Dec 3;551(1-3):125-30. Epub 2006 Sep 9. PubMed PMID: 17027747.

16: Lee B, Kim EY, Kim JH, Min JH, Jeong DW, Jun JY, Cho CY, Sohn Y, Jung HS. Antiallergic effects of peiminine through the regulation of inflammatory mediators in HMC-1 cells. Immunopharmacol Immunotoxicol. 2015;37(4):351-8. doi: 10.3109/08923973.2015.1059441. Epub 2015 Jun 30. PubMed PMID: 26121924.

17: Niu HY, Jin SS, Jia YP, Zhang XX, Yu HS, Song XB. [Comparative Analysis of Content of Four Alkaloids in Fritillaria hupehensis and Fritillaria ebeiensis var. purpurea]. Zhong Yao Cai. 2015 Oct;38(10):2105-8. Chinese. PubMed PMID: 27254925.

18: Wang D, Zhu J, Wang S, Wang X, Ou Y, Wei D, Li X. Antitussive, expectorant and anti-inflammatory alkaloids from Bulbus Fritillariae Cirrhosae. Fitoterapia. 2011 Dec;82(8):1290-4. doi: 10.1016/j.fitote.2011.09.006. Epub 2011 Sep 19. PubMed PMID: 21958967.

19: Lyu Q, Tou F, Su H, Wu X, Chen X, Zheng Z. The natural product peiminine represses colorectal carcinoma tumor growth by inducing autophagic cell death. Biochem Biophys Res Commun. 2015 Jun 19;462(1):38-45. doi: 10.1016/j.bbrc.2015.04.102. Epub 2015 Apr 29. PubMed PMID: 25935480.

20: Li P, Zeng LJ, Li SL, Bi ZM, Lin G. Simultaneous determination of the major isosteroidal alkaloids and their glucosides in the bulbs of Fritillaria by high performance liquid chromatography coupled with evaporative light scattering detection. Yao Xue Xue Bao. 2004 Jan;39(1):56-9. PubMed PMID: 15127583.