ChemicalBook CAS DataBase List 18059-10-4

18059-10-4

Name	Peiminine
CAS	18059-10-4
Molecular Formula	C27H43NO3
MDL Number	MFCD00210542
Molecular Weight	429.64
MOL File	18059-10-4.mol

Chemical Properties

Melting point	267°
alpha	D22 -38.5° (c = 1.5 in chloroform)
Boiling point	567.1±50.0 °C(Predicted)
density	1.18±0.1 g/cm3(Predicted)
storage temp.	-20°C Freezer, Under inert atmosphere
solubility	Chloroform (Slightly), Ethanol (Slightly, Sonicated)
form	Solid
pka	14.56±0.70(Predicted)
color	White to Off-White
InChIKey	IQDIERHFZVCNRZ-MYFUJZFTNA-N
CAS DataBase Reference	18059-10-4(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H332-H312-H302
Precautionary statements	P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312
Safety Statements	24/25 less more
HS Code	29389090

Hazard Information

Description

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.

Definition

ChEBI: Imperialine is an alkaloid.

in vivo

Peiminine (3mg/kg, intraperitoneal injection, single dose) alleviates inflammatory manifestations and mitigates intestinal tissue damage in an experimental model of ulcerative colitis^[2].
Peiminine (10 mg/kg, Intraperitoneal injection, once every 2 days for 6 weeks) prevents bone loss and fat formation in OVX-induced rat model^[3].
Peiminine (1-5 mg/kg, are applied to the dorsal skin, once daily for 16 days) inhibits serum IL-6 and TNF-α in the dinitrochlorobenzene (DNCB)-induced Allergic dermatitis animal model^[4].
Peiminine (2-5 mg/kg, Intraperitoneal injection, once a day for 4 weeks) has a cardioprotective effect against myocardial infarction-induced myocardial injury and fibrosis in myocardial infarction rat model^[5].
Peiminine (1-5 mg/kg, Intraperitoneal injection, single dose) can reduce the damage of inflammatory response to the body and the possibility of pulmonary edema in LPS-induced Acute lung injury model mice^[6].

Animal Model:	ulcerative colitis model^[2]
Dosage:	3mg/kg
Administration:	Intraperitoneal injection (i.p.)
Result:	Reduced inflammation, mucosal ulcers, involvement of digestive system layers, and infltration of inflammatory cells. Reduced the levels of MPO and NO generated in the rectal tissue. Reduced cell proliferation in spleen cell. Decreased the production of f IL-1β, IL-6, and TNF-α cytokines. Reduced expression levels of genes IL-1β, IL-6, TNF-α, iNOS, and COX2.

Animal Model:	Ovariectomized (OVX) rat model^[3]
Dosage:	10 mg/kg
Administration:	Intraperitoneal injection (i.p.)
Result:	Alleviated the bone loss caused by surgical castration. Improved the expression of COL1A1 and β-catenin and reduced the increase expression of PPAR-γ in trabecular bone.

Animal Model:	Allergic dermatitis model^[4]
Dosage:	1 mg/kg, 5 mg/kg
Administration:	were applied to the dorsal skin
Result:	Alleviated the bone loss caused by surgical castration. Improved the expression of COL1A1 and β-catenin and reduced the increase expression of PPAR-γ in trabecular bone.

IC 50

Caspase 3; Caspase-8; Caspase-9; PARP-1; ERK1; ERK2; Bcl-2; p65

References

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

Spectrum Detail

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