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Pamaquine

Catalog Number: BT-278675

CAS Number: 491-92-9

Molecular Formula: C19H29N3O

Molecular Weight: 315.5 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

Pamaquine is a synthetic antimalarial drug that was first synthesized in 1947. It belongs to the 8-aminoquinoline class of drugs and is structurally similar to primaquine. Pamaquine has been used in the treatment of malaria, but its use has been limited due to its toxicity and potential side effects.

Properties

CAS Number

491-92-9

Product Name

Pamaquine

IUPAC Name

1-N,1-N-diethyl-4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

Molecular Formula

C19H29N3O

Molecular Weight

315.5 g/mol

InChI

InChI=1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3

InChI Key

QTQWMSOQOSJFBV-UHFFFAOYSA-N

SMILES

CCN(CC)CCCC(C)NC1=C2C(=CC(=C1)OC)C=CC=N2

Solubility

Soluble in DMSO

Synonyms

8-((4-(diethylamino)-1-methylbutyl)amino)-6-methoxyquinoline
pamaquine
pamaquine monohydrochloride
pamaquine monohydroiodide
pamaquine, citrate (1:1)
plasmocide

Canonical SMILES

CCN(CC)CCCC(C)NC1=C2C(=CC(=C1)OC)C=CC=N2

Method of Synthesis or Extraction

Pamaquine can be synthesized by several methods, including the reduction of 8-nitroquinoline with zinc dust, the reduction of 8-nitroquinoline with sodium dithionite, and the reduction of 8-nitroquinoline with sodium borohydride. The efficiency and yield of each method vary, with the reduction of 8-nitroquinoline with sodium borohydride being the most efficient and yielding the highest amount of pamaquine. However, this method is also the most expensive. Environmental and safety considerations must also be taken into account when synthesizing pamaquine, as some of the reagents used in the synthesis process can be hazardous.

Chemical Structure and Biological Activity

Pamaquine has a chemical formula of C15H21N3O and a molecular weight of 259.35 g/mol. Its mechanism of action is not fully understood, but it is believed to act by interfering with the metabolism of the malaria parasite. Pamaquine has been shown to be effective against Plasmodium falciparum, the most deadly species of malaria parasite. It has also been shown to have activity against other species of Plasmodium, including P. vivax and P. ovale. Pamaquine has a high potency, with a minimum inhibitory concentration (MIC) of 0.1-0.5 μM.

Biological Effects

Pamaquine has been shown to have a variety of biological effects on cell function and signal transduction. It has been shown to inhibit the growth of cancer cells and to have anti-inflammatory properties. However, pamaquine also has potential toxic effects, including hemolytic anemia and methemoglobinemia. These toxic effects limit its use in the treatment of malaria.

Applications

In medical research, pamaquine has been used in drug development and clinical trials. It has been shown to be effective in the treatment of malaria, but its toxicity and potential side effects have limited its use. In environmental research, pamaquine has been studied for its effects on ecosystems and its role in pollution management. In industrial research, pamaquine has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations must be taken into account when using pamaquine in industrial settings.

Future Perspectives and Challenges

The current limitations in the use and study of pamaquine include its toxicity and potential side effects. Possible solutions and improvements include the development of new synthetic methods that are more efficient and less hazardous, as well as the development of new formulations that reduce the toxicity of pamaquine. Future trends and prospects in the application of pamaquine in scientific research include the development of new antimalarial drugs that are more effective and less toxic. The challenges in the development of new antimalarial drugs include the emergence of drug-resistant strains of malaria parasites and the high cost of drug development.

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