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Cinchonidine

Catalog Number: BT-264902

CAS Number: 485-71-2

Molecular Formula: C19H22N2O

Molecular Weight: 294.4 g/mol

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Product Introduction

Description

Cinchonidine is a natural alkaloid that is extracted from the bark of the Cinchona tree. It has been used for centuries as a treatment for malaria and other fevers. In recent years, cinchonidine has gained attention for its potential therapeutic applications in various fields, including medical, environmental, and industrial research. This paper aims to provide a comprehensive review of cinchonidine, including its method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, and future perspectives and challenges.

Properties

CAS Number

485-71-2

Product Name

Cinchonidine

IUPAC Name

(R)-[(2S,4S,5R)-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+/m0/s1

InChI Key

KMPWYEUPVWOPIM-KODHJQJWSA-N

SMILES

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

Solubility

0.24 mg/mL
0.2 mg/mL at 25 °C

Synonyms

2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-
cinchonidine
cinchonidine hydrochloride
cinchonidine monohydrochloride
cinchonidine sulfate(2:1)
cinchonidine, (1beta,3alpha,4beta,8alpha,9R)-isome

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

Cinchonidine can be synthesized using various methods, including the Pictet-Spengler reaction, the Bischler-Napieralski reaction, and the Skraup synthesis. The most commonly used method for cinchonidine synthesis is the Pictet-Spengler reaction, which involves the condensation of an aldehyde or ketone with an amine in the presence of an acid catalyst. The efficiency and yield of each method vary depending on the starting materials and reaction conditions. The Pictet-Spengler reaction has been reported to yield up to 80% cinchonidine. However, the environmental and safety considerations of each method should also be taken into account. For example, the Skraup synthesis involves the use of toxic reagents, such as arsenic and sulfuric acid, which can pose a risk to human health and the environment.

Chemical Structure and Biological Activity

Cinchonidine has a complex chemical structure, consisting of a quinoline ring and a quinuclidine ring. It has been shown to exhibit a wide range of biological activities, including antimalarial, antitumor, and anti-inflammatory effects. The mechanism of action of cinchonidine involves its ability to inhibit the growth and replication of parasites, cancer cells, and inflammatory mediators. Cinchonidine has also been found to interact with various biological targets, such as DNA, RNA, and enzymes.

Biological Effects

Cinchonidine has been shown to have a significant impact on cell function and signal transduction. It has been reported to induce apoptosis in cancer cells, inhibit the production of inflammatory cytokines, and modulate the activity of ion channels and receptors. However, cinchonidine can also have potential therapeutic and toxic effects, depending on the dose and duration of exposure. For example, cinchonidine has been reported to cause cardiotoxicity and neurotoxicity at high doses.

Applications

Cinchonidine has various applications in medical, environmental, and industrial research. In medical research, cinchonidine has been used as a lead compound for drug development, particularly for the treatment of malaria and cancer. Clinical trials have shown promising results for the use of cinchonidine in combination with other drugs for the treatment of malaria and as a chemosensitizer for cancer therapy. However, the potential side effects of cinchonidine should also be considered. In environmental research, cinchonidine has been studied for its effects on ecosystems and its role in pollution management. Cinchonidine has been found to have a low environmental impact and can be used as a natural pesticide. In industrial research, cinchonidine has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations should also be taken into account when using cinchonidine in industrial applications.

Future Perspectives and Challenges

Despite the potential applications of cinchonidine, there are still limitations in its use and study. For example, the low solubility and bioavailability of cinchonidine can limit its effectiveness as a drug. Possible solutions and improvements include the development of new formulations and delivery systems. Future trends and prospects in the application of cinchonidine in scientific research include the identification of new biological targets and the optimization of its pharmacological properties. However, challenges such as the high cost of production and the need for further safety and toxicity studies should also be addressed.
Conclusion:
Cinchonidine is a natural alkaloid with a complex chemical structure and a wide range of biological activities. Its potential applications in medical, environmental, and industrial research make it a promising compound for further study. However, the efficiency, safety, and toxicity considerations of cinchonidine should also be taken into account. Future research should focus on addressing the limitations and challenges of cinchonidine and optimizing its pharmacological properties for various applications.

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