Graduate Pharmacy Aptitude Test (GPAT): Pharmaceutical Chemistry Syllabus

The Graduate Pharmacy Aptitude Test (GPAT), opens doors to infinite opportunities for students from pharmaceutical domain. GPAT is a National level entrance exam for admission into prestigious NIPERs and University colleges. Since 2009, the importance of GPAT has increased as the branch turned into a autonomous exam and separated from GATE (PY). The exam will be conducted by National Testing Agency (NTA) from 2019, previously by AICTE under the guidance of MHRD, India.

Syllabus prescribed by NTA for GPAT includes PHARMACEUTICAL CHEMISTRY is a major subject with topics that are elaborated below.

ORGANIC CHEMISTRY

  • General Principles
    • A brief review of classification & sources of organic compounds, sp3, sp2, sp hybridization, sigma & pi- bonds, bond lengths, bond angles & bond energies along  with their significance in reactions should be carried out.
    • An overview of bond polarization, hydrogen bonds, inductive effects, resonance, and hyper conjugation be taken.
    • Concept of homolytic & heterolytic bond fission, acidity & basicity with different theories should be covered briefly.
    • Ease of formation & order of stabilities of  electron deficient & electron rich species along with the reasons for the same should be covered.
    • Relationships between energy content, stability, reactivity & their importance in chemical reactions should be covered. Calculations for determining empirical & molecular formula should be covered.
  • Different classes of Compounds
    • The following classes of compounds should be taught in detail with respect to their IUPAC/systematic nomenclature, industrial [wherever applicable] & laboratory methods of preparations, physical properties & chemical reactions with emphasis on reaction mechanisms [arrow based] & stereochemistry [wherever applicable].
      • Alkanes [including cyclic compounds]
      • Alkenes [including cyclic compounds]
      • Alkynes [only open chain compounds]
      • Aliphatic hydroxyl compounds
      • Alkyl halides
      • Aldehydes & ketones
      • Carboxylic acids
      • All functional derivatives of carboxylic acids.
  • Protection & Deprotection of Groups
    • Introduction to protection & deprotection of functional groups. Two examples each for amino, hydroxyl, & carbonyl groups. The significance of these in syntheses should be explained.
  • Aromaticity & Aromatic Chemistry
    • Concept of aromaticity, Huckel’s rule & its use in determining the aromatic / nonaromatic character of a compound. A brief coverage of structure of benzene. Detailed  coverage of electophilic & nucleophilic aromatic substitution reactions. Reactivity &orientation in these reactions. Reactivity & orientation in mono- & disubstituted benzenes. Benzyne mechanism.
  • Different Aromatic Classes of Compounds
    • The following classes of compounds with respect to their IUPAC / systematic nomenclature, industrial [wherever applicable] & laboratory methods of preparations,  physical properties & chemical reactions with emphasis on reaction mechanisms [arrow based] & stereochemistry [wherever applicable].
      •  Aromatic hydrocarbons.
      •  Phenolic compounds.
      •  Aromatic & aliphatic amines.
      •  Diazonium salts.
      •  Aromatic nitro- compounds, aryl halides, & ethers.
  • Polycyclic Aromatic Hydrocarbons
    • Syntheses & reactions with mechanisms of bi & tricyclic fused carbocyclic rings like naphthalene, anthracene, & phenanthrene.
  • Carbonyl Chemistry
    • Carbonyl chemistry involving group conversions & their reaction mechanisms along with stereochemistry wherever applicable.
      • Wolf-Kishner reduction & Huang-Minlong modification.
      • Reduction of arylsulfonyl hydrazine / hydrazones to alkanes.
      • Bamford Steven reaction.
      • DCC Oxidation of alcohol.
      • Michael addition / 1,4-addition / conjugate addition.
      • Mannich condensation / reaction.
      • Robinson annulation.
      • Stobbe condensation.
      • Darzen’s glysidic ester synthesis.
      • Beckmann rearrangement.
      • Baeyer Villiger rearrangement.
      • Curtius, Wolff, & Lossen rearrangements.
      • Willgerodt rearrangement.
      • Pinacol-pinacolone rearrangement.
      • Methylene transfer reactions. Use of diazomethane & sulphurylides in the same.
    • Mono- & dialkylations in 1,3-dicarbonyl compounds.
    • Formation & use of enol ethers, enol acetates & enamines as protective groups & in regiospecific alkylations.
  • Heterocyclic Chemistrv
    • IUPAC Nomenclature of heterocyclic rings [3-10 membered] containing O, S, & N  atoms. Nomenclature of above rings containing mono-,di-, & multiple [same or different] heteroatoms should also be covered. Nomenclature of 2 & 3 fused rings containing mono-, di-, & multiple heteroatoms [same or different] should also be covered. Syntheses & reactions of three to six membered rings in detail. Syntheses of five & six membered rings containing mono- or any di- heteroatoms [O, S, & N].
    • Syntheses of quinoline, isoquinoline, benzoxole, benzthiole, & benzazole, benzdiazole, benzoxazole, & benzthiazole.
  • Bridged Rings
    • Bridged ring systems & their nomenclature.
  • Kinetic & Thermodynamic Control
    • Kinetic & thermodynamic control of sulfonation, enolate anion formation & alkylation of enamine reactions.
  • Stereochemistry
    • Stereochemistry. Chirality & asymmetry [introduction of the same to S, P, & N].
    • Definition & classification [different types of isomerisms]. Enantiomers, diastereomers. Enantiomerism & diastereomerism. Meso compounds & their optical activity. Stereochemistry in acyclic compounds.  Newman projection formulae & their significance. Conformational analysis of n- butane. Absolute & relative configuration.
    • Assigning R & S configuration based on Cahn Ingold & Prelog system. Racemic mixture- its definition & resolution. Definitions of terms stereoselective, stereospecific, Enantiomeric excess & distereomeric excess. Stereochemistry in cyclic systems.
    • Conformations of cyclohexane. Cis – trans relationship in cyclohexane. Prediction of stability of different conformations of 1, 2- 1,3- & 1,4- disubstituted cyclohexanes.
    • Effect of multiple substitutions on the stability of cyclohexane conformations. Chair conformations of cis-, & trans-decalins,  perhydrophenanthrenes, & a tetracyclic steroidal nucleus. An introduction to atropisomerism.
  • Carbohydrates
    • Carbohydrates. Definition & classification. D & L nomenclature in sugars. Different ways of drawing / representing a sugar molecule [including cyclic Structure], interconversion of these representations. Anomers & epimers. Mutarotation. Reactions of glucose. Chain extension & chain reduction of a sugar.
  •  Amino Acids & Proteins
    • Amino acids & proteins. Definition & classification. D & L Amino acids, natural, essential, & non-essential amino acids. Denaturation, Strecker, Gabriel phthalimide methods for the preparation of amino acids.
    • Peptide bond & its formation. Two protective groups each, for -NH2 & -COOH functionalities during protein synthesis. Sequencing of a protein by chemical & enzymatic methods.
  • Organometalic Chemistry
    • Organometalic chemistry [preparation & few reactions] of Cu & Boron.
  • Pericyclic Reactions
    • Pericyclic reactions. Concept of HOMO & LUMO. Drawing of HOMO & LUMO of 1, 3- butadiene, allylic cation, radical & anion, & 1, 3, 5-hexatriene. Meaning of conrotatory & disrotatory. Allowed & disallowed thermal & photochemical reactions.
    • Introduction to sigmatropic, electrocyclic & (4n + 2) cycloaddition reactions. Cope, oxy-cope [Claisen rearrangement], Diel’s-Alder & retro Diel’s Alder reaction.

INORGANIC CHEMISTRY

  • Pharmaceutical Impurities
    • Impurities in pharmaceutical substances, sources, types & effects of impurities. Limit tests for heavy metals like lead, iron, arsenic, mercury & for chloride & sulphate as per Indian Pharmacopoeia [I. P.].
  • Monographs
    • Monograph & its importance, various tests included in monographs as per I. P. A study  of the following compounds with respect to their methods of preparation, assay, &pharmaceutical uses: sodium citrate, calcium carbonate, copper sulphate, light & heavy kaolin, ammonium chloride & ferrous gluconate.
  • Isotopes
    • Isotopes- stable & radioactive, mode & rate of decay. Types & measurement of radioactivity. Radiopharmaceuticals & their diagnostic & therapeutic applications in pharmacy & medicine such as 125I, 32P, 51Cr, 60Co, 59Fe, 99Tc-M. Radiocontrast media, use of BaSO4 in medicine.
  • Therapeutic classes of drugs
    • The following topics should be dealt with covering nomenclature [including stereochemical aspects], biological activity [including side & toxic effects ], mode of action, structure activity relationship [where ever applicable] & syntheses of reasonable molecules.
      • Dentifrices, desensitizing agents, & anticaris agents.
      • General anesthetics.
      • Local anesthetics.
      • Antiseptics, disinfectants, sterilants, & astringents.
      • Purgatives, laxatives & antidiarrhoeal agents.
      • Diagnostic agents.
      • Coagulants, anticoagulants & plasma expanders.

MEDICINAL CHEMISTRY

  • Drug Metabolism
    • Introduction to drug metabolism based on the functional groups.
  • Various Classes of Therapeutic Agents
    • A detailed study of the following classes with respect to drug nomenclature, classification, physicochemical properties, mode of action [MOA], structure activity relationships [SAR], wherever applicable, synthesis of simple & prototype molecules, drug metabolism, therapeutic uses & side effects. Drug resistance, wherever applicable, should be covered in respective classes of drugs.
      • Antiamoebic agents.
      • Anthelmintic agents.
      • Antibacterial sulpha drugs [only].
      • Quinolone antibacterials.
      • Antimycobacterial drugs.
      • Antifungal agents.
      • Antiviral agents including HIV & anti-HIV drugs.
      • Thyroid & anti thyroid drugs.
      • Antiallergic agents.
      • Antiulcer agents & Proton Pump Inhibitors.
      • Hypoglycemic agents.
      • Antimalerials
  • Different Classes of Therapeutic Agents
    • A detailed study of the following classes with respect to drug nomenclature, classification, physicochemical properties, mode of action [MOA] , structure activity relationships [SAR] , wherever applicable, synthesis of simple & prototype molecules, drug metabolism, therapeutic uses & side effects. Drug resistance, wherever applicable, should be covered in respective classes of drugs.
      • Sedative-hypnotics
      • Anti-epileptic agents.
      • Neuroleptics.
      • Anti-anxiety drugs.
      • Diuretics.
      • Antibiotics. Penicillins, cephalosporins & other beta- lactam antibiotics like imipenam & aztreonam. Beta-lactamase inhibitors such as clavulanic acid & sulbactum. Chloramphenicol. Tetracyclines. Aminoglycoside antibiotics.
      • Macrolide antibiotics. Lincomycins. Polypeptide antibiotics. Anticancer antibiotics.
      • Steroids. Corticosteroids [gluco- & mineralocorticoids] & anti-inflammatory steroids. Sex steroids. Male & female contraceptive agents. Anabolic steroids.
      • Anticancer agents.
  • Different Classes of Therapeutic Drugs
    • A detailed study of the following classes with respect to drug nomenclature, classification, physicochemical properties, mode of action [MOA], biosynthesis, structure activity relationships [SAR], wherever applicable, synthesis of simple & prototype molecules, drug metabolism, therapeutic uses & side effects. Drug resistance, wherever applicable, in respective classes of drugs.
      • Narcotic [centrally acting] analgesics [analgetics]. Morphine & all its structural modifications [peripheral & nuclear]. Narcotic agonists & antagonists [dual & pure]. Non-narcotic analgesics [NSAIDS]. Difference between narcotic & nonnarcotic agents.
      • Adrenergic drugs. Neurotransmitters & their role. General & specific adrenergic agonists & antagonists [up to alpha-2 & beta-2 only].
      • Cholinergic agents. Muscarinic & nicotinic cholinergic agonists & antagonists [upto M2 & N2]. Neuronal [transmission] blockers.
      • Drugs used in neuromuscular disorders. Drugs used in the treatment of Parkinson’s disease. Central & peripheral muscle relaxants.
      • Hypertensive, antihypertensive, & antianginal agents.
      • Eicosanoids. Prostaglandins, prostacyclins, & thromboxanes. Their biochemical role, biosynthesis, & inhibitors.
  • Introduction to Quantitative Structure Activity Relationship. [QSAR]. Linear free energy relationship. Hammett’s equation. Use of substituent constants such as π, σ, Es, & physicochemical parameters such as pKa, partition coefficient, Rm, chemical shifts, molar refractivity, simple & valance molecular connectivity to indicate electronic effects, lipophillic effects, & steric effects. Introduction, methodology, advantages & disadvantages / limitations of Hansch analysis.
  • Asymmetric Synthesis. Chirality, chiral pool, sources of various naturally available chiral compounds. Eutomers, distomers, eudismic ratio. Enantioselectivity & enantiospecificity. Enantiomeric & diasteriomeric excess. Prochiral molecules. Asymmetric synthesis of captopril & propranolol.
  • Combinatorial Chemistry. Introduction & basic terminology. Databases &libraries. Solid phase synthesis technique. Types of supports & linkers, Wang, Rink, & dihydropyran derivatized linkers. Reactions involving these linkers. Manual parallel & automated parallel synthesis. Houghton’s tea bag method, micromanipulation,  recursive deconvolution. Mix & split method for the synthesis of tripeptides. Limitations of combinatorial synthesis. Introduction to  throughput screening.

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