Wednesday, May 6, 2020

Paracetamol Synthesis and Uses Essay - 1091 Words

Paracetamol – Synthesis and Uses Discovered in 1877 by Harmon Northrop Morse at the John Hopkins University, Paracetamol was one of several aniline deriviatives that was found to have analgesic and antipyretic properties (Brodie 23). It was first synthesized by the reduction of p-nitrophenol with tin in glacial acetic acid; however was not used classified as a medication until ten year later (Bertolini 264). Initially, phenacetin, a closely related compound that exhibited similar physiological effects, became the popular over the counter drug for headaches (Bertolini 251). However, later research by Brodie and Axelrod in 1949 found that phenacetin was in fact metabolized into paracetamol within the body (Brodie and Axelrod 60).†¦show more content†¦This is an electrophilic aromatic substitution reaction where a hydrogen on the aromatic ring is replaced with a nitro group. The hydroxyl group on the aromatic ring is an electron-donating group and therefore serves as an ortho-para director. Through the nitration reaction, two products are formed: o-nitrophenol and p-nitrophenol. In comparing the stability of the two resulting products, o-nitrophenol is less stable due to steric hinderance and proximity of the hydroxyl and nitro group to one another. On the other hand, p-nitrophenol does not experience the same steric hinderance since the two group as on opposite sides of the aromatic ring and therefore do not interfere with one another. As a result, p-nitrophenol is the major product of reaction. It is also the product of interest and will be involved in the next step of the synthesis. Subsequently, p-nitrophenol is reduced by sodium borohydride to give 4-aminophenol. In an industrial synthesis, hydrogenation is used for reduction instead of sodium borohydride to produce an identical product(Travis 764). The use of hydrogenation is more efficient when produce larger quantities. In the last step of the synthesis, 4-aminophenol is acylated in a reaction with acetic anhydride. In this reaction, the electron pair on nitrogen of the amine group attack the one of the carbonyls on the acid anhydride. The electrons move up to the oxygen, forming a negative anion, and a bond is formedShow MoreRelatedThe National Collaborating Centre For Women And Childrens Health Case Study905 Words   |  4 Pagesand Childrens Health (2013), emphasising the importance of avoiding unnecessary treatment in children with a self-limiting viral illness, while The World Health Organisation (2000) recommends the management of fever in children to include the use of paracetamol for children with fever of 39 oC or over. Insufficient data, however support this recommendation. Shann (1995), explains how temperatures above the usual febrile maximum (41 oC) are usually caused by heat stroke or brain injury. 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