General objectives
The course aims to provide students with theoretical and practical knowledge related to the detection and qualitative identification of organic substances of pharmaceutical interest. Students will be guided in studying the correlation between the molecular structure of a pharmaceutical compound and its chemical-physical parameters, so that they will be able to identify the structure of a substance listed in the Official Pharmacopoeia by selecting an appropriate analytical pathway (both instrumental and chemical) for its identification. The course also aims to provide knowledge for the quali-quantitative identification of pharmaceutical substances using instrumental analytical techniques.
At the end of the course, the student must demonstrate that he/she has acquired the specific objectives as follows:
Specific Objectives
1. Knowledge and understanding: At the end of the course, students will have knowledge of the aspects related to the identification of compounds included in the Official Pharmacopoeia and they will be able to interpret the procedures described in the monographs. They will understand acid-base properties and the main reactions used for the identification of functional groups in organic molecules. They will also understand the relationships between molecular structure, physical states, and solubility profiles, and will be familiar with the main techniques for the purification of mixtures of chemical compounds. Furthermore, students will be able to describe the theoretical principles and applications of instrumental analytical techniques.
2. Applying knowledge and understanding: At the end of the course, students will be able to correctly apply the experimental procedures described in the Official Pharmacopoeia for the identification of an unknown substance. They will understand the chemical reactivity exploited for separation and identification. They will recognize how the acid-base properties of functional groups in a drug’s structure can influence its solubility, stability, and reactivity. In addition, they will know the instrumental techniques for the quali-quantitative determination of compounds of pharmaceutical interest.
3. Critical and judgmental skills: The lessons will be characterized by an interactive approach that will serve not only to verify the level of comprehension but also to guide students in establishing connections among the different topics covered. In this way, the study of this course will be perceived not only as an autonomous body of knowledge but also as a bridge connecting previously studied subjects (General and Inorganic Chemistry, Organic Chemistry, Analytical Chemistry, Physics, Drug Analysis I) with those that will follow in the Degree Program (Pharmaceutical Chemistry, Biochemistry, Pharmacology, Pharmacognosy, Toxicology, Pharmaceutical Technology).
4. Communication skills: Students will be able to demonstrate their ability to apply the acquired knowledge to critically address analytical-pharmaceutical problems and to communicate the concepts learned with clarity and appropriate scientific language. Assessment of learning will be carried out through an exam that will cover the entire course program, with particular emphasis on the student’s ability to critically elaborate and communicate the acquired knowledge with clarity and a good command of language.
5. Learning skills: At the end of the course, students will be able to independently evaluate an analytical pathway for active pharmaceutical ingredients (APIs) contained in pharmaceutical formulations. They will also have developed learning skills and the ability to self-assess their preparation, to continue future studies with a good degree of autonomy and awareness.
The course aims to provide students with theoretical and practical knowledge related to the detection and qualitative identification of organic substances of pharmaceutical interest. Students will be guided in studying the correlation between the molecular structure of a pharmaceutical compound and its chemical-physical parameters, so that they will be able to identify the structure of a substance listed in the Official Pharmacopoeia by selecting an appropriate analytical pathway (both instrumental and chemical) for its identification. The course also aims to provide knowledge for the quali-quantitative identification of pharmaceutical substances using instrumental analytical techniques.
At the end of the course, the student must demonstrate that he/she has acquired the specific objectives as follows:
Specific Objectives
1. Knowledge and understanding: At the end of the course, students will have knowledge of the aspects related to the identification of compounds included in the Official Pharmacopoeia and they will be able to interpret the procedures described in the monographs. They will understand acid-base properties and the main reactions used for the identification of functional groups in organic molecules. They will also understand the relationships between molecular structure, physical states, and solubility profiles, and will be familiar with the main techniques for the purification of mixtures of chemical compounds. Furthermore, students will be able to describe the theoretical principles and applications of instrumental analytical techniques.
2. Applying knowledge and understanding: At the end of the course, students will be able to correctly apply the experimental procedures described in the Official Pharmacopoeia for the identification of an unknown substance. They will understand the chemical reactivity exploited for separation and identification. They will recognize how the acid-base properties of functional groups in a drug’s structure can influence its solubility, stability, and reactivity. In addition, they will know the instrumental techniques for the quali-quantitative determination of compounds of pharmaceutical interest.
3. Critical and judgmental skills: The lessons will be characterized by an interactive approach that will serve not only to verify the level of comprehension but also to guide students in establishing connections among the different topics covered. In this way, the study of this course will be perceived not only as an autonomous body of knowledge but also as a bridge connecting previously studied subjects (General and Inorganic Chemistry, Organic Chemistry, Analytical Chemistry, Physics, Drug Analysis I) with those that will follow in the Degree Program (Pharmaceutical Chemistry, Biochemistry, Pharmacology, Pharmacognosy, Toxicology, Pharmaceutical Technology).
4. Communication skills: Students will be able to demonstrate their ability to apply the acquired knowledge to critically address analytical-pharmaceutical problems and to communicate the concepts learned with clarity and appropriate scientific language. Assessment of learning will be carried out through an exam that will cover the entire course program, with particular emphasis on the student’s ability to critically elaborate and communicate the acquired knowledge with clarity and a good command of language.
5. Learning skills: At the end of the course, students will be able to independently evaluate an analytical pathway for active pharmaceutical ingredients (APIs) contained in pharmaceutical formulations. They will also have developed learning skills and the ability to self-assess their preparation, to continue future studies with a good degree of autonomy and awareness.
scheda docente
materiale didattico
2. Overview of the contents of the Pharmacopoeia and selected monographs.
3. Molecular analysis: a. Melting point. b. Boiling point. c. Refractometry. d. Determination of absolute and relative density. e. Polarimetry.
4. Structural Analysis: a. Preliminary Examinations: evaluation of solubility, factors influencing it, characteristics of solvents, effect of pH. Solubility of substances in acid and base solutions. b. Organoleptic examination. c. Behavior upon calcination. d. Qualitative elemental analysis: Lassaigne's assay. e. Assays for the detection of the aromatic ring and unsaturations. f. Physical properties, solubility, and detection tests for the most common functional groups.
5. Separation and Purification Methods: a. Separation techniques for homogeneous mixtures: 1) Solvent extraction and extraction methods; 2) Crystallization; 3) Distillation; 4) Chromatography: Introduction, classification of chromatographic methods, most frequently used solid, liquid, and chemically bonded stationary phases; chromatographic separation mechanisms. b. Separation techniques for heterogeneous mixtures: 1) Sublimation; 2) Filtration; 3) Centrifugation.
6. Chromatographic separation techniques: a. Paper chromatography (PC) and thin-layer chromatography (TLC). b. Column chromatography (CC). c. High-performance liquid chromatography (HPLC). d. Gas chromatography (GC).
7. Hyphenated techniques: High-performance liquid chromatography and photodiode array detector (HPLC-DAD); -performance liquid chromatography and mass spectrometry (HPLC-MS); Gas chromatography and mass spectrometry (GC-MS).
8. Instrumental characterization and analysis techniques: a. Mass spectrometry. b. Spectroscopic analysis – IR absorption spectroscopy. c. Spectroscopic analysis – NMR spectroscopy: 1H NMR and 13C NMR (overview). c. Classroom exercises on IR and NMR spectroscopy involving active student participation.
Laboratory sessions focused on topics covered during lectures.
- Cavrini, V.; Andrisano, V. Principi di Analisi Farmaceutica, Ed. Esculapio: For chromatography and coupled techniques
- Silverstein, R. M.; Webster, F. X.; Kiemle, D. J.; Bryce, D. L. Identificazione Spettrometrica di Composti Organici, Ed. Ambrosiana: For mass spectrometry, for IR and NMR spectroscopy
- Chiappe, C.; D’Andrea, F. Tecniche Spettroscopiche e Identificazione di Composti Organici, Ed. ETS: For mass spectrometry, for IR and NMR spectroscopy
- Carrieri, A. Manuale di Analisi Quantitativa dei Medicinali, Ed. EdiSES: For chromatography and for the spectrometric identification of organic compounds
Programma
1. Safety elements in the chemical laboratory.2. Overview of the contents of the Pharmacopoeia and selected monographs.
3. Molecular analysis: a. Melting point. b. Boiling point. c. Refractometry. d. Determination of absolute and relative density. e. Polarimetry.
4. Structural Analysis: a. Preliminary Examinations: evaluation of solubility, factors influencing it, characteristics of solvents, effect of pH. Solubility of substances in acid and base solutions. b. Organoleptic examination. c. Behavior upon calcination. d. Qualitative elemental analysis: Lassaigne's assay. e. Assays for the detection of the aromatic ring and unsaturations. f. Physical properties, solubility, and detection tests for the most common functional groups.
5. Separation and Purification Methods: a. Separation techniques for homogeneous mixtures: 1) Solvent extraction and extraction methods; 2) Crystallization; 3) Distillation; 4) Chromatography: Introduction, classification of chromatographic methods, most frequently used solid, liquid, and chemically bonded stationary phases; chromatographic separation mechanisms. b. Separation techniques for heterogeneous mixtures: 1) Sublimation; 2) Filtration; 3) Centrifugation.
6. Chromatographic separation techniques: a. Paper chromatography (PC) and thin-layer chromatography (TLC). b. Column chromatography (CC). c. High-performance liquid chromatography (HPLC). d. Gas chromatography (GC).
7. Hyphenated techniques: High-performance liquid chromatography and photodiode array detector (HPLC-DAD); -performance liquid chromatography and mass spectrometry (HPLC-MS); Gas chromatography and mass spectrometry (GC-MS).
8. Instrumental characterization and analysis techniques: a. Mass spectrometry. b. Spectroscopic analysis – IR absorption spectroscopy. c. Spectroscopic analysis – NMR spectroscopy: 1H NMR and 13C NMR (overview). c. Classroom exercises on IR and NMR spectroscopy involving active student participation.
Laboratory sessions focused on topics covered during lectures.
Testi Adottati
- Caliendo, G. Manuale di Analisi Qualitativa, Ed. EdiSES: For separation and purification methods, molecular and structural analysis- Cavrini, V.; Andrisano, V. Principi di Analisi Farmaceutica, Ed. Esculapio: For chromatography and coupled techniques
- Silverstein, R. M.; Webster, F. X.; Kiemle, D. J.; Bryce, D. L. Identificazione Spettrometrica di Composti Organici, Ed. Ambrosiana: For mass spectrometry, for IR and NMR spectroscopy
- Chiappe, C.; D’Andrea, F. Tecniche Spettroscopiche e Identificazione di Composti Organici, Ed. ETS: For mass spectrometry, for IR and NMR spectroscopy
- Carrieri, A. Manuale di Analisi Quantitativa dei Medicinali, Ed. EdiSES: For chromatography and for the spectrometric identification of organic compounds
Modalità Erogazione
The course is composed of both theoretical and practical lessons. The theoretical sessions will alternate between lectures and activities characteristic of the active learning (such as think-pair-share) and collaborative learning, that will include methodologies of cooperative learning (such as the learning together or the group investigation techniques) and of inductive teaching (such as inquiry-based learning, with particular reference to problem-based learning and project-based learning). This approach will allow to guide students through both deductive and inductive learning paths.Modalità Frequenza
The attendance of the course is compulsory for both lectures and laboratory exercisesModalità Valutazione
The assessment method consists of a single examination in a mixed mode (written and oral) divided into two parts: 1) Spectroscopic analysis exercise (IR and NMR): this component evaluates the student’s ability to independently and critically process the provided analytical data to identify the substance under examination; 2) oral examination: this part assesses the student’s knowledge and understanding of the topics covered throughout the course. The elements considered for evaluation include mastery of the course content in all parts of the program, the use of appropriate scientific language, active participation in lectures and laboratory experiences, reasoning ability demonstrated during the oral examination, and the capacity for independent study using the recommended textbooks. Passing the exam with the minimum grade (18/30) requires an overall sufficient knowledge of the topics covered. Achieving the highest grade (30/30 with honors) requires an excellent and comprehensive understanding of all course topics, along with the ability to establish logical and coherent connections among them.