Catalogo dei Corsi di studio

This course provides the student with the theoretical knowledge and technical skills to perform drug analysis and identification through analytical chemistry and spectroscopic methods.
By completing Drug Analysis I, the student acquires:
1. Theoretical knowledge of the most common methods of separating and purifying chemical substances (extraction methods, chromatography, distillation, sublimation and crystallization), of the most common instrumental chemical analysis techniques to determine physicochemical measurements (melting point, boiling point, density, refractive index and specific optical rotation) and of qualitative chemical structural analyses including molecular spectroscopy (identification of functional groups, and UV-visible, infrared (IR), nuclear magnetic resonance (NMR) spectroscopies) through theoretical lecture-based classes.
2. The ability to apply that theoretical knowledge. The student attends individual teaching laboratory lectures where he applies purification and identification methods to pharmaceutical substances. Moreover, the student attends additional practical lectures in which he practices on how to read infrared and NMR spectra to identify chemical substances.
3. Self-direction and to act independently to a level where the student has a practical understanding of the learned techniques. At the end of the teaching laboratory lectures, the student has to identify and characterize unknown chemical substances given in the Pharmacopeia. Moreover, during the final oral test the student has to identify unknown chemical substances by reading infrared and NMR spectra.
4. Written and oral communications skills, to a level where the student can clearly communicate the conclusions of a chemical and spectroscopic analysis. This is evaluated during the final test.
5. To develop subject-related practical and cognitive skills. The course provides the student with the core elements for both further courses and the final test of the Pharmacy programme.

Programme

This course provides the student with the theoretical knowledge and technical skills to perform drug analysis and identification through analytical chemistry and spectroscopic methods.
Curriculum content of lecture-based classes:
1. Aspects of security and safety in a chemistry laboratory. (2 hours)
2. Pharmacopeia contents and monographs. (2 hours)
3. Separation and purification methods (12 hours)
- Solvent extraction and pH dependency; liquid-liquid extraction; continuous extraction; solid-liquid extraction; solid-liquid extraction with Soxhlet.
- Mixture separation through liquid-liquid extraction.
- Chromatography: introduction; classification of chromatographic methods; mostly used solid and liquid stationary phases; separation mechanism (partition, expanded bed absorption, ion exchange, displacement, affinity). Planar chromatography on paper and TLC. Column chromatography.
- Distillation: isobar and isotherm diagrams of ideal mixtures; simple distillation, vacuum distillation and fractional distillation of ideal and real mixtures; homogeneous and heterogeneous azeotropes; azeotropic distillation, steam distillation.
- Crystallization: principles and methods.
- Sublimation: principles and methods.
4. Chemical molecular analysis. (10 hours)
- Melting point: theoretical and technical principles, effect of impurities on melting point, methods.
- Boiling point: methods. Effect of impurities on boiling point.
- Refraction index: methods, Abbe refractometer.
- Absolute density and relative density: methods, pycnometer and Mohr-Westphal scale.
- Polarimetry.
5. Chemical structural analyses (18 hours)
- Preliminary assays: solubility, solvents, pH dependency. Solubility in acidic or basic solutions.
- Organoleptic assay.
- Calcination.
- Lassaigne assay.
- Identification assay for aromaticity and saturation.
- Carboxylic acid identification: physical properties, solubility, acidity, identification assays.
- Esters identification: physical properties, solubility, identification assays. Hydrolysis.
- Lactones identification: physical properties, solubility, identification assays.
- Amides identification: Esters identification: physical properties, solubility, identification assays. Hydrolysis.
- Nitriles identification: physical properties, solubility, identification assays.
- Amines identification: physical properties, solubility, basicity, identification assays. Hinsberg method for the detection of primary, secondary and tertiary amines.
- Amino acids identification: physical properties, solubility, identification assays.
- Ketones and aldehydes identification: physical properties, solubility, carbonyl group reactivity, identification assays.
- Carbohydrates identification: physical properties, solubility, identification assays.
- Alcohols identification: physical properties, solubility, identification assays.
- Ethers and phenol identification: physical properties, solubility, identification assays.
- Halogenated compounds identification: halogenated carboxylic compounds, halogenated alkyls and aryls (physical properties, solubility, identification assays).
- Sulphurated compounds identification: sulphates, sulphonic acids, thiols, thiophenols, thioethers, disulphures (physical properties, solubility, identification assays).
6. Spectroscopic methods. (18 hours)
- UV-Vis spectroscopy: electronic transitions, Lambert-Beer law. Instruments: light source, grating monochromator, prism monochromator, holder for the sample, phototubes, photomultiplier tubes. Influence on the absorbance. Application of UV-Vis spectroscopy to quantitative and qualitative analyses. Solvent and pH dependency on phenols and aromatic amine determination. FT spectroscopy.
- IR spectroscopy: introduction, mechanic and harmonic models. Vibrational modes of linear and nonlinear compounds. Number of vibrational modes. Factors that influence IR resonance. Instruments. FT-IR. Sample preparation. Spectra interpretation. Catachrestic bands of functional groups.
- NMR spectroscopy: introduction, instruments, solvents for sample preparation. 1H NMR: chemical shift, TMS as zero, signal intensity, integrals, spin-spin coupling, multiples analysis. Spectra interpretation. 13CNMR: principles.

10 hours of flipped classroom for analysis of IR and IR spectra.

Individual teaching laboratory lectures (60 hours):
- Separation of a mixture by liquid/liquid extraction.
- Crystallization.
- Sublimation.
- Calcination.
- Solubility assay.
- Melting point determination.
- Functional groups identification according to the Pharmacopeia.
- TLC analysis of Anise seeds extract
- TLC analysis of Calcium pantothenate.
- Identification of unknown substances given in the Pharmacopeia.

Adopted texts

Recommended books to be added to the lecture notes:
Caliendo G. - Manuale di Analisi Qualitativa - EDISES
Silverstein, Webster, Kieml, Bryce - Identificazione spettrometrica di composti organici – III° ed. –Ed. Ambrosiana

Reference books
Farmacopea Ufficiale della Repubblica Italiana XII Ed.

Prerequisites

For a better understanding of the theoretical knowledge and technical skills, the student must have learned: - General chemistry and organic chemistry, necessary prerequisites for understanding the theoretical knowledge of the separation and purification methods. - General chemistry and organic chemistry, necessary prerequisites for understanding the theoretical knowledge of the chemical analysis techniques and molecular spectroscopy. - Physics, important prerequisites for understanding the theoretical knowledge of analysis techniques and molecular spectroscopy. For attending Drug Analysis I, student must have attended Pharmaceutical Analytical Chemistry.

Study modes

Attendance of the course is mandatory, both for the lectures and for the practical exercises.This course provides the student with the theoretical knowledge and technical skills to perform drug analysis and identification through analytical chemistry and spectroscopic methods. 62 hours lectures will be used to deliver the core material. 10 hours of flipped classroom for analysis of IR and NMR spectra. The practical sessions will complement the material presented in lectures by 60 hours individual teaching laboratory lectures. It will provide guidance and experience of following written experimental procedures and help students to consolidate their practical skills and the subsequent reporting and analysis of practical results.

Frequency modes

Attendance of the course is mandatory, both for classroom lessons and for laboratory practice. The presence is checked daily by the teacher.

Exam modes

The of examination method is chosen with the aim of verifying the acquisition of the theoretical and technical-practical knowledge necessary to purify and identify compounds of pharmaceutical interest.
The assessment of skills is ascertained through two tests:
1. At the end of the teaching laboratory lectures, the student has to identify and characterize two unknown chemical substances given in the Pharmacopeia. Self-direction and to act independently in choosing the right analytical process will be assessed. The test takes 8 hours divided by two laboratory lectures.
2. End-of-course exam is divided into two parts:
- A written part where the student has to interpret simple spectroscopic data (IR, 1H NMR and 13C NMR spectra) in terms of absorption bands, chemical shifts, integration traces and spin-spin coupling patterns. This part will take half an hour.
- An oral part where both theoretical and practical knowledge of the most common methods of separating and purifying chemical substances (extraction methods, chromatography, distillation, sublimation and crystallization), of the most common instrumental chemical analysis techniques to determine physicochemical measurements (melting point, boiling point, density, refractive index and specific optical rotation) and of qualitative chemical structural analyses (identification of functional groups) and UV-visible, infrared (IR), nuclear magnetic resonance (NMR) will be assessed. This part will take half an hour.
Passing the exam takes place with a grade of not less than 18/30. Student must demonstrate that he has acquired sufficient knowledge of spectroscopic analysis and the main methods of separation and purification and a basic knowledge of recognition assays.
To achieve a score of 30/30 cum laude, the student must instead demonstrate that he has acquired an excellent knowledge of all the topics covered during the course, being able to connect them in a logical and coherent way.

Programme

This course provides the student with the theoretical knowledge and technical skills to perform drug analysis and identification through analytical chemistry and spectroscopic methods.
Curriculum content of lecture-based classes:
1. Aspects of security and safety in a chemistry laboratory. (2 hours)
2. Pharmacopeia contents and monographs. (2 hours)
3. Separation and purification methods (12 hours)
- Solvent extraction and pH dependency; liquid-liquid extraction; continuous extraction; solid-liquid extraction; solid-liquid extraction with Soxhlet.
- Mixture separation through liquid-liquid extraction.
- Chromatography: introduction; classification of chromatographic methods; mostly used solid and liquid stationary phases; separation mechanism (partition, expanded bed absorption, ion exchange, displacement, affinity). Planar chromatography on paper and TLC. Column chromatography.
- Distillation: isobar and isotherm diagrams of ideal mixtures; simple distillation, vacuum distillation and fractional distillation of ideal and real mixtures; homogeneous and heterogeneous azeotropes; azeotropic distillation, steam distillation.
- Crystallization: principles and methods.
- Sublimation: principles and methods.
4. Chemical molecular analysis. (10 hours)
- Melting point: theoretical and technical principles, effect of impurities on melting point, methods.
- Boiling point: methods. Effect of impurities on boiling point.
- Refraction index: methods, Abbe refractometer.
- Absolute density and relative density: methods, pycnometer and Mohr-Westphal scale.
- Polarimetry.
5. Chemical structural analyses (18 hours)
- Preliminary assays: solubility, solvents, pH dependency. Solubility in acidic or basic solutions.
- Organoleptic assay.
- Calcination.
- Lassaigne assay.
- Identification assay for aromaticity and saturation.
- Carboxylic acid identification: physical properties, solubility, acidity, identification assays.
- Esters identification: physical properties, solubility, identification assays. Hydrolysis.
- Lactones identification: physical properties, solubility, identification assays.
- Amides identification: Esters identification: physical properties, solubility, identification assays. Hydrolysis.
- Nitriles identification: physical properties, solubility, identification assays.
- Amines identification: physical properties, solubility, basicity, identification assays. Hinsberg method for the detection of primary, secondary and tertiary amines.
- Amino acids identification: physical properties, solubility, identification assays.
- Ketones and aldehydes identification: physical properties, solubility, carbonyl group reactivity, identification assays.
- Carbohydrates identification: physical properties, solubility, identification assays.
- Alcohols identification: physical properties, solubility, identification assays.
- Ethers and phenol identification: physical properties, solubility, identification assays.
- Halogenated compounds identification: halogenated carboxylic compounds, halogenated alkyls and aryls (physical properties, solubility, identification assays).
- Sulphurated compounds identification: sulphates, sulphonic acids, thiols, thiophenols, thioethers, disulphures (physical properties, solubility, identification assays).
6. Spectroscopic methods. (18 hours)
- UV-Vis spectroscopy: electronic transitions, Lambert-Beer law. Instruments: light source, grating monochromator, prism monochromator, holder for the sample, phototubes, photomultiplier tubes. Influence on the absorbance. Application of UV-Vis spectroscopy to quantitative and qualitative analyses. Solvent and pH dependency on phenols and aromatic amine determination. FT spectroscopy.
- IR spectroscopy: introduction, mechanic and harmonic models. Vibrational modes of linear and nonlinear compounds. Number of vibrational modes. Factors that influence IR resonance. Instruments. FT-IR. Sample preparation. Spectra interpretation. Catachrestic bands of functional groups.
- NMR spectroscopy: introduction, instruments, solvents for sample preparation. 1H NMR: chemical shift, TMS as zero, signal intensity, integrals, spin-spin coupling, multiples analysis. Spectra interpretation. 13CNMR: principles.

10 hours of flipped classroom for analysis of IR and IR spectra.

Individual teaching laboratory lectures (60 hours):
- Separation of a mixture by liquid/liquid extraction.
- Crystallization.
- Sublimation.
- Calcination.
- Lassaigne assay.
- Solubility assay.
- Melting point determination.
- Functional groups identification according to the Pharmacopeia.
- TLC analysis of Calcium pantothenate.
- Identification of unknown substances given in the Pharmacopeia.

Adopted texts

- Caliendo, G. Manuale di Analisi Qualitativa EdiSES

- Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Identificazione spettrometrica di composti organici, Ed. Ambrosiana

Prerequisites

For a better understanding of the theoretical knowledge and technical skills, the student must have learned: - General chemistry and organic chemistry, necessary prerequisites for understanding the theoretical knowledge of the separation and purification methods. - General chemistry and organic chemistry, necessary prerequisites for understanding the theoretical knowledge of the chemical analysis techniques and molecular spectroscopy. - Physics, important prerequisites for understanding the theoretical knowledge of analysis techniques and molecular spectroscopy. For attending Drug Analysis I, student must have attended Pharmaceutical Analytical Chemistry.

Exam modes

The assessment strategy is designed to verify student ability in critically evaluating and representing theoretical and practical knowledge acquired during the course.

Assessment strategy:
- At the end of the teaching laboratory lectures, the student has to identify and characterize two unknown chemical substances given in the Pharmacopeia. Self-direction and to act independently in choosing the right analytical process will be assessed. The test takes 8 hours divided by two laboratory lectures.
- End-of-course written exam consists of:
o A first part where the student has to interpret simple spectroscopic data (IR, 1H NMR and 13C NMR spectra) in terms of absorption bands, chemical shifts, integration traces and spin-spin coupling patterns.
o A second part where both theoretical and practical knowledge of the most common methods of separating and purifying chemical substances (extraction methods, chromatography, distillation, sublimation and crystallization), of the most common instrumental chemical analysis techniques to determine physicochemical measurements (melting point, boiling point, density, refractive index and specific optical rotation) and of qualitative chemical structural analyses (identification of functional groups) and UV-visible, infrared (IR), nuclear magnetic resonance (NMR) will be assessed.
It is a requirement that the major categories of assessment are passed separately in order to achieve an overall pass.