Imperialine | CAS#61825-98-7 | antitussive

MedKoo Cat#: 558129 | Name: Imperialine

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Description:

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

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

Chemical Structure

Imperialine

CAS#61825-98-7

Theoretical Analysis

MedKoo Cat#: 558129

Name: Imperialine

CAS#: 61825-98-7

Chemical Formula: C27H43NO3

Exact Mass: 429.3243

Molecular Weight: 429.65

Elemental Analysis: C, 75.48; H, 10.09; N, 3.26; O, 11.17

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Related CAS #

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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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sipeimine is a natural product isolated from Fritillaria ussuriensis.

In vitro activity:

The cell proliferation test revealed that Peiminine could suppress the proliferation of 12z cells, with the inhibitory impact proportional to the concentration (Figure 5C, 5D). Reference: Am J Transl Res. 2022 Sep 15;14(9):6196-6209. https://pubmed.ncbi.nlm.nih.gov/36247281/

In vivo activity:

After pretreatment with sipeimine, this study measured several ferroptosis-related proteins, including Nrf2, GPX4, HO-1, SLC7A11 and FTH1. Western blot indicated that the expression of Nrf2, GPX4, HO-1, SLC7A11 and FTH1 were significantly diminished in the PM2.5 group in comparison with the sham group. These changes were reversed with the pretreatment of sipeimine (Fig. 3A and Fig. 3B). The immunofluorescence staining revealed significantly decreased Nrf2 expression in the PM2.5 group, and sipeimine upregulated Nrf2 expression in a dose-dependent manner (Fig. 3C and Fig. 3D). As shown in Fig. 4A and B, the administration of RSL3 reversed the upregulation of Nrf2, GPX4 and HO-1 induced by sipeimine. Reference: Ecotoxicol Environ Saf. 2022 Jul 1;239:113615. https://pubmed.ncbi.nlm.nih.gov/35567927/

	Solvent	mg/mL	mM
Solubility
	DMSO	8.3	19.39

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

1. Peng X, Xia Y, Xie J, Liu H, Fan L, Yu C, Ni X. Mechanism of Thunberg Fritillaria in treating endometriosis based on network pharmacology and the effect of Peiminine on the MEK/ERK pathway. Am J Transl Res. 2022 Sep 15;14(9):6196-6209. PMID: 36247281; PMCID: PMC9556459. 2. Chen ZK, Zhao D, Feng SX, Xu J. Pharmacodynamics and Cellular Uptake of Peimine and Peiminine in Inflammatory Model Non-Small-Cell Lung Cancer Epithelial Cells (A549). Evid Based Complement Alternat Med. 2022 Feb 7;2022:2946201. doi: 10.1155/2022/2946201. PMID: 35178100; PMCID: PMC8843782. 3. Wang Y, Shen Z, Zhao S, Huang D, Wang X, Wu Y, Pei C, Shi S, Jia N, He Y, Wang Z. Sipeimine ameliorates PM2.5-induced lung injury by inhibiting ferroptosis via the PI3K/Akt/Nrf2 pathway: A network pharmacology approach. Ecotoxicol Environ Saf. 2022 Jul 1;239:113615. doi: 10.1016/j.ecoenv.2022.113615. Epub 2022 May 12. PMID: 35567927. 4. Chen P, Zhou D, Liu Y, Wang P, Wang W. Peiminine inhibits myocardial injury and fibrosis after myocardial infarction in rats by regulating mitogen-activated protein kinase pathway. Korean J Physiol Pharmacol. 2022 Mar 1;26(2):87-94. doi: 10.4196/kjpp.2022.26.2.87. PMID: 35203059; PMCID: PMC8890941.

In vitro protocol:

In vivo protocol:

1. Wang Y, Shen Z, Zhao S, Huang D, Wang X, Wu Y, Pei C, Shi S, Jia N, He Y, Wang Z. Sipeimine ameliorates PM2.5-induced lung injury by inhibiting ferroptosis via the PI3K/Akt/Nrf2 pathway: A network pharmacology approach. Ecotoxicol Environ Saf. 2022 Jul 1;239:113615. doi: 10.1016/j.ecoenv.2022.113615. Epub 2022 May 12. PMID: 35567927. 2. Chen P, Zhou D, Liu Y, Wang P, Wang W. Peiminine inhibits myocardial injury and fibrosis after myocardial infarction in rats by regulating mitogen-activated protein kinase pathway. Korean J Physiol Pharmacol. 2022 Mar 1;26(2):87-94. doi: 10.4196/kjpp.2022.26.2.87. PMID: 35203059; PMCID: PMC8890941.

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.