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4,7-Dichloroquinoline was first reported in a patent filed by IG Farben in 1937. [2] However, its synthesis was not investigated in detail until chloroquine was developed as an antimalarial drug. [ 3 ] : 130–132 A route to the intermediate starting from 3-chloroaniline was developed by chemists at Winthrop Chemical Co .
Serious side effects include problems with vision, muscle damage, seizures, and low blood cell levels. [ 1 ] [ 4 ] Chloroquine is a member of the drug class 4-aminoquinoline . [ 1 ] As an antimalarial, it works against the asexual form of the malaria parasite in the stage of its life cycle within the red blood cell . [ 1 ]
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A 6 electron cyclization reaction with the loss of another ethanol molecule forms a quinoline (ethyl 4-oxo-4,4a-dihydroquinoline-3-carboxylate). The enol form can be represented from the keto form through keto-enol tautomerism. Protonation of the nitrogen forms ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate. Mechanism for the Gould-Jacobs reaction
One of the most serious side effects is retinopathy (generally with chronic use). [ 3 ] [ 20 ] People taking 400 mg of hydroxychloroquine or less per day generally have a negligible risk of macular toxicity, whereas the risk begins to increase when a person takes the medication over five years or has a cumulative dose of more than 1000 grams.
The most common side effects include nausea, constipation, tiredness, somnolence (sleepiness), decreased appetite, and decreased weight. [ 5 ] Atogepant was approved for medical use in the United States in September 2021, [ 4 ] [ 8 ] and in the European Union in August 2023.