Peimine

CAS# 23496-41-5

Peimine

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Chemical structure

Peimine

3D structure

Chemical Properties of Peimine

Cas No. 23496-41-5 SDF Download SDF
PubChem ID 131900 Appearance Powder
Formula C27H45NO3 M.Wt 431.66
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Verticine; Dihydroisoimperialine
Solubility DMSO : 50 mg/mL (115.83 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
SMILES CC1CCC2C(C3CCC4C(C3CN2C1)CC5C4CC(C6C5(CCC(C6)O)C)O)(C)O
Standard InChIKey IUKLSMSEHKDIIP-BZMYINFQSA-N
Standard InChI InChI=1S/C27H45NO3/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/h15-25,29-31H,4-14H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-,22-,23+,24-,25-,26+,27-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Peimine

The bulbus of Fritillaria thunbergii Miq.

Biological Activity of Peimine

DescriptionPeimine has good anti-inflammatory effects in vivo, it inhibits the production of inflammatory cytokines induced by LPS through blocking MAPKs and NF-κB signaling pathways. It also has antitussive and sedative actions, the action being suspected to be central in nature.
TargetsIL Receptor | TNF-α | NF-kB | p65 | p38MAPK | ERK | JNK | IkB | IKK
In vitro

Peimine impairs pro-inflammatory cytokine secretion through the inhibition of the activation of NF-κB and MAPK in LPS-induced RAW264.7 macrophages.[Pubmed: 23944357]

Immunopharmacol Immunotoxicol. 2013 Oct;35(5):567-72.

In the previous study, we found that Peimine has good anti-inflammatory effects in vivo. However, the anti-inflammatory mechanism of Peimine remains unclear. We, therefore, assessed the effects of Peimine on inflammatory cytokines in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages.
METHODS AND RESULTS:
We found that Peimine (0-25 mg/L) significantly inhibited tumor necrosis factor (TNF)-α, interleukin (IL)-6, IL-1β, and increased IL-10 production. Furthermore, Peimine significantly inhibited the phosphorylation of p38, ERK and c-jun N-terminal kinase (JNK) as well as decreased p65 and IκB.
CONCLUSIONS:
The present results indicate that Peimine inhibits the production of inflammatory cytokines induced by LPS through blocking MAPKs and NF-κB signaling pathways.

In vivo

Comparative pharmacokinetic studies of peimine and peiminine in rat plasma by LC-MS-MS after oral administration of Fritillaria thunbergii Miq. and Fritillaria thunbergii Miq. - Glycyrrhiza uralensis Fisch. couple extract.[Pubmed: 22026124]

Pharmazie. 2011 Sep;66(9):684-9.


METHODS AND RESULTS:
A sensitive LC-MS-MS method has been successfully applied to pharmacokinetic study of Peimine and peiminine in rat plasma after oral administration of Fritillaria thunbergii Miq. exact and Fritillaria thunbergii Miq. - Glycyrrhiza uralensis Fisch. couple extract. The results indicated that plasma profiles of Peimine and peiminine confirmed to two-compartment open model with weighting function of 1/C2 for data fitting and parameter estimation and the utilization with Glycyrrhiza uralensis Fisch. could decrease C(max) and prolong MRT(0-infinity) and t1/2 of Peimine remarkly with the bioavailability of Peimine remained practically unchanged. Meanwhile, the concentration of Peimine in rat plasma was more stable.
CONCLUSIONS:
Nevertheless, there were no significant differences among all calculated parameters of peiminine.

Studies on the antitussive and sedative activities of peimine and peiminine.[Reference: WebLink]

Acta Pharmaceutica Sinica, 1985, 20(4):306-8.

The antitussive and sedative activities of Peimine and peiminine, two alkaloids isolated from Fritillaria verticillata Willd var thunbergii Bak, were investigated in laboratory.
METHODS AND RESULTS:
The EDT_(50) (the time needed to make 50% mice cough) was prolonged to 130% of the control when Peimine or peiminine 4 mg/kg was administered orally to mice induced to cough by atomized ammonium hydroxide. A 45% inhibition rate of cough amplitude was observed in anesthetized guinea pig induced to cough by stimulation of the mucosa at the tracheal bifurcation with a bristle after a sc injection of Peimine or peiminine 4 mg/kg. Peak action appeared 30~60 minutes after the injection. In cats, induced to cough by electrical stimulation at the central stump of the superior laryngeal nerve, both the incidence and amplitude of cough reflex were inhibited by sc injection of 4 mg/kg of Peimine or peiminine. The action lasted for an hour or so.The spontaneous activities of mice were significantly decreased by Peimine or peiminine after sc injection of a dose of 2 mg/kg. Furthermore, the CNS stimulating action of caffeine was antagonized and the sedative action of chlorpromazine was potentiated by Peimine and peiminine in mice at the same dose level. It appears that both Peimine and peiminine have antitussive and sedative actions, the former action being suspected to be central in nature.
CONCLUSIONS:
However, no difference of pharmacological action, either qualitatively or quantitatively, between peiminine and peiminine has thus far been demonstrated.

Peimine Dilution Calculator

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Peimine Molarity Calculator

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Preparing Stock Solutions of Peimine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3166 mL 11.5832 mL 23.1664 mL 46.3328 mL 57.916 mL
5 mM 0.4633 mL 2.3166 mL 4.6333 mL 9.2666 mL 11.5832 mL
10 mM 0.2317 mL 1.1583 mL 2.3166 mL 4.6333 mL 5.7916 mL
50 mM 0.0463 mL 0.2317 mL 0.4633 mL 0.9267 mL 1.1583 mL
100 mM 0.0232 mL 0.1158 mL 0.2317 mL 0.4633 mL 0.5792 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Peimine

Peimine(Dihydroisoimperialine; Verticine) is a natural compound with good anti-inflammatory effects in vivo. IC50 value: Target: Peimine (0-25 mg/L) significantly inhibited tumor necrosis factor (TNF)-α, interleukin (IL)-6, IL-1β, and increased IL-10 production. Furthermore, peimine significantly inhibited the phosphorylation of p38, ERK and c-jun N-terminal kinase (JNK) as well as decreased p65 and IκB.

References:
[1]. Yi PF, et al. Peimine impairs pro-inflammatory cytokine secretion through the inhibition of the activation of NF-κB and MAPK in LPS-induced RAW264.7 macrophages. Immunopharmacol Immunotoxicol. 2013 Oct;35(5):567-72.

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References on Peimine

Comparative pharmacokinetic studies of peimine and peiminine in rat plasma by LC-MS-MS after oral administration of Fritillaria thunbergii Miq. and Fritillaria thunbergii Miq. - Glycyrrhiza uralensis Fisch. couple extract.[Pubmed:22026124]

Pharmazie. 2011 Sep;66(9):684-9.

A sensitive LC-MS-MS method has been successfully applied to pharmacokinetic study of Peimine and peiminine in rat plasma after oral administration of Fritillaria thunbergii Miq. exact and Fritillaria thunbergii Miq. - Glycyrrhiza uralensis Fisch. couple extract. The results indicated that plasma profiles of Peimine and peiminine confirmed to two-compartment open model with weighting function of 1/C2 for data fitting and parameter estimation and the utilization with Glycyrrhiza uralensis Fisch. could decrease C(max) and prolong MRT(0-infinity) and t1/2 of Peimine remarkly with the bioavailability of Peimine remained practically unchanged. Meanwhile, the concentration of Peimine in rat plasma was more stable. Nevertheless, there were no significant differences among all calculated parameters of peiminine.

Peimine impairs pro-inflammatory cytokine secretion through the inhibition of the activation of NF-kappaB and MAPK in LPS-induced RAW264.7 macrophages.[Pubmed:23944357]

Immunopharmacol Immunotoxicol. 2013 Oct;35(5):567-72.

In the previous study, we found that Peimine has good anti-inflammatory effects in vivo. However, the anti-inflammatory mechanism of Peimine remains unclear. We, therefore, assessed the effects of Peimine on inflammatory cytokines in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. We found that Peimine (0-25 mg/L) significantly inhibited tumor necrosis factor (TNF)-alpha, interleukin (IL)-6, IL-1beta, and increased IL-10 production. Furthermore, Peimine significantly inhibited the phosphorylation of p38, ERK and c-jun N-terminal kinase (JNK) as well as decreased p65 and IkappaB. The present results indicate that Peimine inhibits the production of inflammatory cytokines induced by LPS through blocking MAPKs and NF-kappaB signaling pathways.

Description

Peimine(Dihydroisoimperialine; Verticine) is a natural compound with good anti-inflammatory effects in vivo.

Keywords:

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