Organic Chemistry In Pharmaceutical Industry

Introduction

Aromaticity is defined as a property of the conjugated cycloalkenes , which enhances amolecule's stabilization due to its ability todelocalize electrons present in the orbitals of π . For example benzene is an aromatic compound . Benzene is primarily used as an Intermediate material to produce other chemicals which is used in different fields of life . Benzene is mainly used as a precursor to the manufacturing of more complex chemical compounds , such as acetaminophen . we will discuss aromaticity , benzene with its structure , its properties and its uses in addition to one of benzene derivatives as acetaminophen , its structure , metabolism and its uses.

Aromaticity

The first use of the term “aromatic” was in an article by August Wilhelm Hofmann in 1855. Aromaticity is a property of cyclic , planar structures with a ring of resonance bonds giving greater stability compared to other geometric or connective arrangements with the same set of atoms . Aromatic molecules are very stable and are not easily breaking apart to react with other substances. Organic compounds which are not aromatic are known as aliphatic compounds which may be cyclical but only aromatic rings have particular stability .[1]

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Benzene

Benzene is the simplest organic , aromatic hydrocarbon and parent compound of numerous important aromatic compounds . In 1825 Benzene was first found by the English scientist Michael Faraday. [2] who extracted the compound from a liquid residue obtained by heating whale's oil. He called the extracted compound 'pheno' from the Greek word “phainein' which means to illuminate. In 1834, the molecular formula of benzene was determined to be C6H6 by the German scientist EilhardtMitscerlich who called the compound 'benzin' that was then changed after time to 'benzene'. Benzene also was found in the Solar System , the atmospheres of Jupiter , Saturn and the moon Titan of Saturn by (Fouchet et al . 2005).[3]

Structure of benzene

In1866, Kekulé proposed that benzene (C6H6) had a cyclic structure in which the six carbons were linked in a hexagonal ring with alternating single and double carbon. To carbon bonds and each carbon linked to one hydrogen . Kekulé suggested that benzene was a combination of two forms in rapid equilibrium , or 'hybrid resonance.' [4] Acompound with delocalized electrons is usually more stable than it would be if all of their electrons were localized. The extra stability which a compound gains from having electrons relocated is called 'resonance energy.'

Chemical and physical priorities of benzene

Pure benzene is a colourless, strongly refracting liquid with characteristic odour, boiling at 80.4 °and solidifying on cooling to rhombic prisms , which melt at 5.5 ° (D20 = 0·87865) . It is dissoluble in water, but is miscible with alcohol, ether, carbon disulphide and other organic solvents ; it is a very good solvent for fats , resins and higher aromatic hydrocarbons .[6] It evaporates very easily into the air, and slowly dissolves in water. It is highly flammable and is produced both from natural processes and from human activity.[5]

Uses of benzene

Many companies use benzene to produce other chemicals that are used to manufacture plastics , resins and synthetic and nylon fibres. Benzene is also used to make rubber, lubricants , dyes , detergents and drugs . One of these drugs is acetaminophen “paracetamol”

Acetaminophen

Analgesics are pain relief compounds and antipyretics are compounds used to alleviate fever . One common medication that does both is aspirin , acetaminophen . Acetaminophen that is mostly used by people with unwanted adverse aspirin side effects . It also Can be found in over 100 products either alone or in combination with other medications.[7] Acetaminophen , which can be synthesized from p-aminophenol , under the trade name Tylenol is typically better known.

Structure of acetaminophen

Acetaminophen is called in IUPAC as N-(4-hydroxyphenyl ) acetamide and its chemical formula is C8H9NO2 and its extended formula is HOC6H4NHCOCH3. Acetaminophen is a benzene ring center , substituted by one hydroxyl group and the amide nitrogen atom in the para . there are four different routes to prepare acetaminophen.

Metabolism of acetaminophen

Acetaminophen is rapidly absorbed from the gastrointestinal ( GI ) tract after ingestion , and spread rapidly across the body. Max concentrations of it in plasma are reached within 30 to 60 minutes . Acetaminophen is metabolized extensively by the liver by three key hepatic pathways : glucuronidation , sulfation , and oxidation of CYP450 2E1. Approximately 90 per cent of acetaminophen is conjugated to renally removed sulfated and glucuronidated metabolites . Approximately 2 per cent of the remaining acetaminophen is excreted unchanged in the urine and the rest undergo CYP450-mediated oxidation to form a reactive metabolite , N-acetyl - p-benzoquinone imine (NAPQI). Under normal circumstances , this toxic metabolite reacts in glutathione with sulfhydryl groups, converting them to harmless metabolites before they are excreted in the urine.[9]

Uses of acetaminophen

The World Health Organization (WHO) has expanded its advice for the use of acetaminophen , recommending acetaminophen as the first step in any pharmacological treatment of pain . in many chronic pain conditions such as osteoarthritis and geriatric patients in general , acetaminophen is recommended as first-line treatment . The broad approval of acetaminophen is attributable primarily to a favorable safety profile compared to other treatment options. [8]

Conclusion

Aromatic molecules are very stable , so they do not split so easily and even react with other types of substances . Benzene , toluene , ortho-xylene , and para-xylene are key aromatic hydrocarbons of commercial interest . Each year around 35 million tons are produced worldwide . Benzene is used to produce many chemical compounds and drugs like acetaminophen which use to treatment pain.

References

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4. Student book Dr. Eman Mohamed & Dr. NohaElnagdi& Dr. Adel Ghitary, 2019, Pharmacentical Organic Chemistry 1, faculty of pharmacy MTI, p. 1:11
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