18059-10-4

Basic information

• Product Name: Peiminine
• Synonyms: PEIMININE;PEINININE;RADDEANINE;3beta,20-Dihydroxy-5alpha-cevan-6-one;Cevan-6-one,3,20-dihydroxy-, (3β,5α)-;Fritillarine;Osnovanine;PEIMINE (RG)
• CAS NO: 18059-10-4
• Molecular Formula: C27H43NO3
• Molecular Weight: 429.64
• Product Categories: Steroids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 18059-10-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 267°
• Boiling Point: 567.1 °C at 760 mmHg
• Flash Point: 296.8 °C
• Appearance: /
• Density: 1.18 g/cm³
• Refractive Index: 1.585
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethanol (Slightly, Sonicated)
• PKA: 14.56±0.70(Predicted)
• CAS DataBase Reference: Peiminine(CAS DataBase Reference)
• NIST Chemistry Reference: Peiminine(18059-10-4)
• EPA Substance Registry System: Peiminine(18059-10-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 18059-10-4(Hazardous Substances Data)

Usage

Description

Peiminine is a natural product found in Fritillaria anhuiensis, Fritillaria ebeiensis, and other organisms with data available.It has been reported to have potent anti-inflammatory, antitussive, and expectorant effects. It induces autophagic cell death thus represses colorectal carcinoma tumor growth.Corydalis ochotensis var. raddeana also yields this alkaloid which must not be confused with the two bases of the same name previously isolated from Fritillaria raddeana. The structure has been determined from chemical analysis and the ultraviolet, infrared, NMR and mass spectra.

Chemical Properties

Peiminine is an alkaloid isolated from the Chinese drug 'Pei-Mu', the 'Szechuan' variety of which is stated to be obtained from the corms of Fritillaria RoyZei Hook. This base was first prepared by Chou and Chen who gave it the formula C18H22O2N. Other formulae assigned to the alkaloid are C26H43O2N and C25H41O3N. Peiminine yields colourless needles from EtOH and is laevorotatory having [a]D18 - 67.3° (EtOH). It forms a hydrochloride, m.p. 295-8°C; hydrobromide, m.p. 292°C; oxime, m.p. 10SoC (dec.); semicarbazone, m.p. 255-6°C and the phenylhydrazone hydrochloride, m.p. 266°C. The acetyl derivative yields colourless needles from Me2CO, m.p. 174°C, giving a hydrochloride, m.p. 268°C. Chi and his co-workers have found that the free base sinters at 140°C, melts at 147- 8°C and again at 225-6°C after intermediate solidification. These authors consider the alkaloid to be identical with verticilline (q.v.).

Uses

Peiminine is a derivative of Peimine (P218375) a steroidal alkaloid compound extracted from the Fritillaria species of medicinal plants.

References

Kametani et al., Heterocycles, 4, 723 (1976)

InChI:InChI=1/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

Upstream product

• 77410-35-6 C₂₇H₄₃NO₄ 

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