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Cinchonine

Catalog Number: BT-264904

CAS Number: 118-10-5

Molecular Formula: C19H22N2O

Molecular Weight: 294.4 g/mol

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Product Introduction

Description

Cinchonine is an alkaloid found in the bark of the Cinchona tree, which is native to South America. It has been used for centuries as a natural remedy for malaria and other fevers. Cinchonine has also been studied for its potential therapeutic effects in various diseases, including cancer, Alzheimer's disease, and Parkinson's disease. This paper aims to provide a comprehensive review of cinchonine, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges.

Properties

CAS Number

118-10-5

Product Name

Cinchonine

IUPAC Name

[(4R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol

Molecular Formula

C19H22N2O

Molecular Weight

294.4 g/mol

InChI

InChI=1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13?,14-,18?,19?/m1/s1

InChI Key

KMPWYEUPVWOPIM-UHFFFAOYSA-N

SMILES

C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O

Solubility

0.24 mg/mL
0.2 mg/mL at 25 °C

Synonyms

cinchonine
cinchonine, hexaiodoTl(-2) (1:1), (9S)-isomer
cinchonine, hydrochloride, (9S)-isomer
cinchonine, monohydrochloride, (9S)-isomer
cinchonine, sulfate (2:1), (9S)-isomer
LA 40221
LA-40221

Canonical SMILES

C=CC1CN2CCC1CC2C(C3=CC=NC4=CC=CC=C34)O

Isomeric SMILES

C=C[C@@H]1CN2CC[C@@H]1C[C@H]2[C@@H](C3=CC=NC4=CC=CC=C34)O

Method of Synthesis or Extraction

Cinchonine can be synthesized or extracted from the bark of the Cinchona tree. The commonly used methods for extraction include maceration, percolation, and Soxhlet extraction. The efficiency and yield of each method depend on various factors, such as the type of solvent used, the duration of extraction, and the quality of the bark. Maceration is the simplest and most commonly used method, but it has a lower yield compared to percolation and Soxhlet extraction. Environmental and safety considerations should also be taken into account when choosing the method of extraction, as some solvents can be toxic and harmful to the environment.

Chemical Structure and Biological Activity

Cinchonine has a complex chemical structure, consisting of a quinoline ring and a quinuclidine ring. It has been shown to have various biological activities, including antimalarial, antitumor, and anti-inflammatory effects. The mechanism of action of cinchonine involves its ability to inhibit the growth and replication of parasites and cancer cells. It also modulates various signaling pathways involved in inflammation and cell proliferation. Cinchonine has been found to be more potent than its stereoisomer, quinine, in some biological assays.

Biological Effects

Cinchonine has been shown to have various effects on cell function and signal transduction. It has been found to induce apoptosis (programmed cell death) in cancer cells, inhibit the production of pro-inflammatory cytokines, and modulate the activity of ion channels and receptors. However, cinchonine can also have potential toxic effects, such as cardiotoxicity and neurotoxicity, which should be carefully evaluated in preclinical and clinical studies. The potential therapeutic effects of cinchonine in various diseases, such as malaria, cancer, and neurodegenerative diseases, are currently being investigated.

Applications

Cinchonine has various applications in scientific research, including its role in drug development, clinical trials, and findings. It has been used as a lead compound for the development of new antimalarial and anticancer drugs. Cinchonine has also been studied for its potential use in the treatment of Alzheimer's disease and Parkinson's disease. In environmental research, cinchonine has been found to have effects on ecosystems and can be used in pollution management. In industrial research, cinchonine has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations should be taken into account when using cinchonine in industrial applications.

Future Perspectives and Challenges

Despite the potential therapeutic benefits of cinchonine, there are still limitations in its use and study. The low solubility and bioavailability of cinchonine can limit its effectiveness in vivo. The potential toxic effects of cinchonine also need to be carefully evaluated in clinical trials. Possible solutions and improvements include the development of new formulations and delivery systems to improve the solubility and bioavailability of cinchonine. Future trends and prospects in the application of cinchonine in scientific research include its potential use in combination therapy and personalized medicine.
Conclusion:
Cinchonine is a complex alkaloid with various biological activities and potential therapeutic benefits. Its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges have been discussed in this paper. Further research is needed to fully understand the potential of cinchonine in various diseases and to overcome the limitations in its use and study.

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