Basic information Safety Supplier Related

Penehyclidine HCl (Mixture of IsoMers)

Basic information Safety Supplier Related

Penehyclidine HCl (Mixture of IsoMers) Basic information

Product Name:
Penehyclidine HCl (Mixture of IsoMers)
Synonyms:
  • Penehyclidine HCl (Mixture of IsoMers)
  • Penehyclidine HCl
  • 2-(1-azabicyclo[2.2.2]octan-3-yloxy)-1-cyclopentyl-1-phenylethanol,hydrochloride
  • 2-(1-azabicyclo[2.2.2]oct-3-yloxy)-1-cyclopentyl-1-phenylethanol hydrochloride (1:1)
  • 2-(1-azabicyclo[2.2.2]oct-3-yloxy)-1-cyclopentyl-1-phenyleth...
  • 1-Cyclopentyl-1-phenyl-2-(quinuclidin-3-yloxy)ethanol hydrochloride
  • Benzenemethanol, a-[(1-azabicyclo[2.2.2]oct-3-yloxy)methyl]-a-cyclopentyl-, hydrochloride(1:1)
  • Penehyclidine hydrochloride, 10 mM in DMSO
CAS:
151937-76-7
MF:
C20H30ClNO2
MW:
351.92
Mol File:
151937-76-7.mol
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Penehyclidine HCl (Mixture of IsoMers) Chemical Properties

storage temp. 
-20°C, away from moisture
form 
Liquid
color 
Colorless to light yellow
Water Solubility 
H2O: 2mg/mL, clear
InChI
InChI=1S/C20H29NO2.ClH/c22-20(18-8-4-5-9-18,17-6-2-1-3-7-17)15-23-19-14-21-12-10-16(19)11-13-21;/h1-3,6-7,16,18-19,22H,4-5,8-15H2;1H
InChIKey
DDTVVMRZNVIVQM-UHFFFAOYSA-N
SMILES
C(C1C=CC=CC=1)(C1CCCC1)(O)COC1CN2CCC1CC2.Cl
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Penehyclidine HCl (Mixture of IsoMers) Usage And Synthesis

Uses

Penehyclidine (Penequinine) hydrochloride, a anticholinergic agent, is a selective antagonist of M1 and M3 receptors. Penehyclidine hydrochloride activates NF-kβ in lung tissue and inhibits the release of inflammatory factors. Penehyclidine hydrochloride can alleviate the pulmonary inflammatory response in rats with chronic obstructive pulmonary disease (COPD) undergoing mechanical ventilation[1].

Biological Activity

Penehyclidine hydrochloride is a brain penetrant anticholinergic drug th at exhibits both antimuscarinic and antinicotinic activity. Penehyclidine hydrochloride does not induce muscarinic 2 receptor-associated cardiovascular side effects. Penehyclidine hydrochloride is effective in experimental models of heart, lung and brain ischemia reperfusion injury.

in vivo

Penehyclidine (0.3-3 mg/kg, ip, single dose) exhibits protective activity in rats ALI models[2].
Penehyclidine (1 mg/kg, ip, single dose) enhances the expression of BDNF and phosphorylation of ERK1/2 in the hippocampus, exhibits antidepressant-like effects in mouse CUMS model[4].

Animal Model:rats ALI models[2]
Dosage:0.3-3 mg/kg
Administration:ip, single dose
Result:Alleviated LPS-induced lung injury in rats.
Animal Model:Mouse chronic unpredictable mild stress (CUMS) model[4]
Dosage:1 mg/kg
Administration:ip, single dose
Result:Reduced the immobility time in the forced swimming test (FST) and tail suspension test (TST).

IC 50

mAChR1; mAChR3; NF-κB

References

[1] Zhi-Yuan Chen, et al. The Mechanism of Penehyclidine Hydrochloride and Its Effect on the Inflammatory Response of Lung Tissue in Rats with Chronic Obstructive Pulmonary Disease During Mechanical Ventilation. Int J Chron Obstruct Pulmon Dis. 2021 Mar 31;16:877-885. DOI:10.2147/COPD.S295329
[2] Wang X, et al., Penehyclidine hydrochloride alleviates lipopolysaccharide?induced acute respiratory distress syndrome in cells via regulating autophagy?related pathway. Mol Med Rep. 2021 Feb;23(2):100. DOI:10.3892/mmr.2020.11739
[3] Zi C, et al., Penehyclidine hydrochloride protects against anoxia/reoxygenation injury in cardiomyocytes through ATP-sensitive potassium channels, and the Akt/GSK-3β and Akt/mTOR signaling pathways. Cell Biol Int. 2020 Jun;44(6):1353-1362. DOI:10.1002/cbin.11329
[4] Sun X, et al., A Selective M1 and M3 Receptor Antagonist, Penehyclidine Hydrochloride, Exerts Antidepressant-Like Effect in Mice. Neurochem Res. 2019 Dec;44(12):2723-2732. DOI:10.1007/s11064-019-02891-5

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