ANALISI FARMACEUTICA E NUTRACEUTICO-ALIMENTARE 1 A - L

The course aims to provide the student with basic knowledge relating to the nature, denomination, determination of the chemical composition and quantitative determination of analytes, understood as:

- inorganic and organic pharmaceutical compounds;

-food products relating to the non-nutritional, but functional and therapeutic component;

- nutraceutical products and food supplements.

The aim of the course is to provide the assumptions underlying the use of substances of pharmaceutical interest, food supplements and nutraceuticals in the management of health and prevention of deficiency states.

The course, which includes both classroom lessons and laboratory practice, is divided into two modules (Module A and Module B).

Module A – First semester – Prof. Milena Rizzo

Upon completion of the training activity in Module A, the student:

-should know the structures of the main chemical compounds contained in pharmaceutical formulations, -in functional foods, supplements, and nutraceuticals.

-will have acquired the skills necessary to perform manual and instrumental chemical analyses for the purpose of qualitative recognition.

-has developed critical skills in the analysis of unknown mixtures, where he or she tries his or her hand at interpreting the result of recognition reactions performed in the laboratory.

-has learned to critically discuss the procedural aspects of the analysis performed, applying instrumental analysis methods on pure and mixture analytes.

At the end of the practical laboratory exercises, the students, will have become able to give a correct interpretation of the experimental data obtained and to write a report on the experience made.

Module B – Second semester – Prof. Giuseppe Romeo

On successful completion of module B students will be able to:

-describe the instrumentation and glassware required to perform the considered analytical methods.

-articulate knowledge and understanding of main volumetric and spectrophotometric analytical methods.

-provide a critical evaluation of methods available for quantifying a range of substances of pharmaceutical interest with reference to monographs of the Italian and European Pharmacopoeias.

Moreover, on successful completion of the lab practice, students will be able to:

-weigh a sample with an electronic analytical balance.

-prepare a solution with a known titre of a reagent (primary standard) by means of the proper calibrated glassware.

-transfer a given volume of a liquid or solution by means of calibrated glass pipettes or automatic pipettes.

-perform a titration with the appropriate indicator or a potentiometric apparatus for the determination of the end-point.

-determine, through a volumetric analysis, titre, mass or per cent purity of a given sample.

-calibrate the pHmeter and to use it for the pH measure of solutions.

-prepare the sample and to measure absorbance by means of a UV-Vis spectrophotometer.

-perform spectrophotometric quantitative determinations (even through construction of the calibration line).

-give a correct interpretation of obtained experimental data and to write out a report on the lab experiment.

Module A – First semester – Prof. Milena Rizzo

Module A activities are constituted by class lectures and case studies along with laboratory experiences (single or group work).

During class lectures, all course content is presented in detail. Students are asked to actively discuss presented topic and a number of case studies.

During lab practice, students perform a number of qualitative analyses on compounds of pharmaceutical interest to recognize inorganic and organic anions and cations present in mixture in the given mixture. In lab, students are stimulated to discuss each other and with teachers about practical experiences and subjects seen during class.

At the end of every lab practice, students have to write up and submit a report on the experience. The report is evaluated for the clarity of expression, correctness in the conduction of the analysis and correctness of chemical reactions carried out in recognition assays. The report is given back to the student and commented on during the next lab session.

Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, according to the course content outlined in the syllabus

Information for students with disabilities and /or SLD

To guarantee equal opportunities and in compliance with the laws in force, interested students can ask for a personal interview in order to plan any compensatory and /or dispensatory measures, based on the didactic objectives and specific needs.

 It is also possible to contact the referent teacher CInAP (Center for Active and Participatory Integration - Services for Disabilities and / or SLD) of our Department, prof.ssa Santina Chiechio.

Module B – Second semester – Prof. Giuseppe Romeo

Module B activities are constituted by class lectures and case studies along with laboratory experiences (single or group work).

During class lectures, all course content is presented in detail. Students are asked to actively discuss presented topic and a number of case studies.

During lab practice, students have to critically analyse experimental protocols and perform a number of quantitative analyses on samples of pharmaceutical interest. In lab, students are stimulated to discuss each other and with teachers about practical experiences and subjects seen during class.

At the end of every lab practice, students have to write up and submit a report on the experience. The report is evaluated for the clarity of expression, correctness in the conduction of the analysis and the accuracy and precision of the final result. The report is given back to the student and commented on during the next lab session.

Should teaching be carried out in mixed mode or remotely, it may be necessary to introduce changes with respect to previous statements, according to the course content outlined in the syllabus

Information for students with disabilities and / or SLD

To guarantee equal opportunities and in compliance with the laws in force, interested students can ask for a personal interview in order to plan any compensatory and / or dispensatory measures, based on the didactic objectives and specific needs.

 It is also possible to contact the referent teacher CInAP (Center for Active and Participatory Integration - Services for Disabilities and / or SLD) of our Department, prof.ssa Santina Chiechio.

To fully understand the topics of this course, the student must have basic knowledge of the chemical and biological disciplines proposed by the degree course.

The prerequisites required for effective attendance at the course mainly concern notions of general chemistry (equilibrium in solution, acidity and basicity, pH, oxidation states of the main elements, standard potentials, oxidation-reduction reactions), organic chemistry (features and reactivity of the main classes of organic compounds), analytical chemistry (theoretical aspects of volumetric and spectrophotometric analytical methods).

Mandatory attendance is required for all activities according to the didactic regulation (link: http://www.dsf.unict.it/corsi/lm-13_ctf/regolamento-didattico).

Module A – First semester – Prof. Milena Rizzo

Introduction to the theoretical practical course: general rules for good practice and safety in the laboratory; types of hazards; knowledge of safety pictograms; personal protective equipment; disposal of special waste.

Generalities on the foundational theoretical principles of qualitative analysis: chemical composition and physical form of analytes; solution and solubility product precipitates; acid-base solutions and pH; complexation and stability of complexes and chelates.

Generalities on methods of processing a sample: classification of the nature of the sample (pharmaceutical, food, other); preliminary treatments; purification; sorting of a mixture; methods of extracting a pure analyte.

Generalities on analytical methods: classification; stages of an analysis; applications provided by the Italian and European Official Pharmacopoeia; generalities on qualitative recognition reactions of pure or mixed components.

Semi-micro analysis and main applicable transformation reactions: precipitation, solubilization, oxidation-reduction, complexation.

Generalities on instrumental methods: theoretical principles of optical methods of analysis used in the laboratory; theoretical principles of chromatographic methods of analysis used in the laboratory.

Module A also includes practical laboratory exercises. The schedule of exercises, for each academic year, is established and published at the beginning of the course. A list of some possible exercises is as follows:

1.         Handing over the workstation and personal protective equipment (PPE). Indication of the basic rules for “Safety in the Laboratory”. Indication of how to handle “Special Waste”. Solid-liquid separation by filtration and centrifugation.

2.         Recognition of analytes in purity of inorganic nature by “Dry Way” analysis; Flame assay;

3.         Recognition of analytes in purity of inorganic nature, by analysis by “Wet Way”;

4.         Recognition of analytes in mixture of inorganic nature, by analysis by “Wet Way”;

5.         Recognition of ANIONIC analytes of inorganic nature, by analysis by “Wet Way”;

6.         Recognition of CATIONIC analytes of inorganic nature, by analysis by “Wet Way”;

7.         Sampling and preliminary treatments of a sample: purification; sorting of a mixture; methods of extraction of a pure analyte.

8.         Analysis of a mixture by Thin Layer Chromatography-TLC.

Module B – Second semester – Prof. Giuseppe Romeo

Generalities on chemical quantitative analysis

Materials, reagents and laboratory apparatuses. Laboratory safety. Validation of an analytical method. Accuracy and precision. Outlier tests: 4d test and Dixon’s test. Analytical balances, weighing operations and methods.

Volumetric analysis

Preparation of solution with known concentration; determination of the concentration of solutions. Volumetric glassware and calibration. Calculations in volumetric analysis.

Acid-base titrations. Acidimetric and alkalimetric titrations. Preparation and standardization of acid or basic solutions. Acid-base indicators. Neutralization titrations in non-aqueous solvents: generalities, intrinsic acidity and alkalinity, differentiating and leveling effects, solvent classifications. Equilibria in non-aqueous solvents, criteria for choosing a solvent.

Applications with reference to monographs in Italian Pharmacopoeia XII ed. and European Pharmacopoeia 11th.

Complexometric titrations. Titrations methods. Preparation and standardization of an EDTA solution. Complexometric indicators. Applications with reference to monographs in Italian Pharmacopoeia XII ed. and European Pharmacopoeia 11 th.

Oxidation-reduction titrations. Permanganometry, cerimetry, iodimetry, iodometry, bromometry.

Applications with reference to monographs in Italian Pharmacopoeia XII ed. and European Pharmacopoeia 11 th.

Electroanalytical methods

Potentiometric determination pH. Potentiometric detection of the end-point in titrations. Biamperometric determination of primary aromatic nitrogen: applications described in Italian Pharmacopoeia XII ed. and European Pharmacopoeia 11 th.

Spectroanalytical methods

UV-Visible spectrophotometry. General discussion. Lambert-Beer law. Quantitative analysis: choice of the wavelength (l), general procedures for the quantitative determination. Linear regression analysis. Applications with reference to monographs in Italian Pharmacopoeia XII ed. and European Pharmacopoeia 11 th.

Fluorimetry. Principles and basic features of the technique, instrumentation, applications to the quantitative analysis of pharmaceutical substances.

The Module B includes lab practice. Lab practice schedule, for each academic year, is defined at the beginning of the course. A list of some typical laboratory experiences is the following:

1. Consignment of the work station. Safety in laboratory. Glassware and analytical balance usage.
2. Titre determination of a NaOH solution. Utilization of acid-base indicators.
3. Standardization of a HCl solution by means of anhydrous Na₂CO₃ as primary standard.
4. Quantitative determination of an unknown Na₂CO₃ sample through an acidimetric titration.
5. Standardization of a NaOH solution by means of a suitable primary standard.
6. Quantitative determination of an unknown L-(+) tartaric acid sample through an alkalimetric titration.
7. Quantitative determination of an unknown ascorbic acid (vitamin C) sample through an iodimetric titration.
8. Determination of total hardness in drinking water. Determination of mg/L of Ca⁺⁺ ion and Mg⁺⁺ ion.
9. Determination of per cent purity of a caffeine sample by UV spectrometry. Beer-Lambert law use.
10. pHmeter calibration and use. Potentiometric detection of the end-point in a neutralization titration. Construction of the titration curve.
11. Quantitative determination of an unknown caffeine sample by UV spectrometry. Construction of the calibration line.

Module A – First semester – Prof. Milena Rizzo

Araneo A. Chimica analitica qualitativa. Metodo periodale. Ambrosiana Milano Ed 1993.

L. Mannina, M. Daglia, A. Ritieni: La Chimica e gli alimenti: nutrienti ed aspetti nutraceutici, C.E.A. (2019)

Cavrini V, Andrisano V. Principi di Analisi Farmaceutica. Esculapio ed. 2018

Cappelli P., Vannucchi V., Chimica degli Alimenti, conservazione e trasformazione. Zanichelli ed. 2006.

Farmacopea Ufficiale Italiana XII ed.

European Pharmacopoeia 1^th ed.

Module B – Second semester – Prof. Giuseppe Romeo

1. E. Abignente, D. Melisi, M. G. Rimoli – Principi di analisi quantitativa DEI medicinali - Ed. Loghìa, Napoli
2. A. Carreri - Manuale di Analisi Quantitativa dei Medicinali - EdiSES
3. D. C. Harris - Chimica Analitica Quantitativa - Zanichelli, Bologna
4. R. Cozzi, P. Protti, T. Ruaro - Analisi chimica: moderni metodi strumentali - Zanichelli, Bologna
5. Vogel's Texbook of Quantitative Chemical Analysis - Fifth edition - Ed. Longman Scientific & Tecnical
6. Farmacopea Ufficiale Italiana XII edizione. European Pharmacopoeia 11th edizione e supplementi

Items 1 and 2 are textbooks, 3 - 5 are reference books, Italian and European Pharmacopoeias (item 6) are the sources for official quantitative analyses of pharmaceuticals

The final exam is a written examination to ascertain student’s knowledge and comprehension of syllabus contents and of the practical aspects of laboratory experiences.

To take the exam, students need to book online at Portale studenti of Università di Catania webpage (www.unict.it). Booking list is opened about fifteen days before the exam date. Learning assessment may also be performed online should the conditions require it.

Module A - Prof. Milena Rizzo

Interpretation of Traditional and IUPAC Nomenclature and Writing Structure Formulas of Given Compounds.

Description of the characteristics of a Coordinating Compound.

Description of methods of recognizing the components of a mixture of two inorganic salts.

Writing and balancing of neutralization, complexation and oxidation-reduction reactions.

Colour in Pharmaceutical and Food Chemical Analysis.

Examples of extraction methods applied to plant products of nutraceutical interest.

Module B – Prof. Giuseppe Romeo

Description of the general features of a volumetric analytical technique.

Description of the quantitative analysis of acetylsalicylic acid according to EP 11 th.

Description of the quantitative analysis of nicotinamide according to EP 11 th.

Description of the quantitative analysis of paracetamol according to EP 11 th.

Description of % nitrogen content determination in pharmaceutical and food compounds.

Description of the quantitative analysis of magnesium ions in the presence of calcium ones.

Description of the quantitative analysis of primary aromatic amino-nitrogen according to EP 11 th.

Description of the spectrophotometric quantitative analysis of prednisolone acetate according to EP 11 th.

What do accuracy and precision refer to in a quantitative analysis?

What are the features of primary standards?