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I) PHARMACEUTICAL ORGANIC
CHEMISTRY-I:
The General Objectives:
The different branches of
chemistry and mainly organic chemistry is the corner stone
in understanding other subjects which are majors for
students of pharmacy such as pharmaceutical chemistry ,
pharmaceutics, pharmacology , biochemistry , pathology
...etc. The recent explosive development of molecular
biology and genetic engineering makes it imperative for
students of pharmacy and other biological sciences to have a
strong background in Organic Chemistry. The naturally
occuring organic compounds are of concern to the specialists
in biological sciences as well as to the organic chemists,
and indeed it is in dealing with such substances that
biochemistry, medicinal chemistry, and organic chemistry
come together and lose their individual identity. The
naturally occuring compounds include the proteins, fats,
carbohydrates, vitamins, and hormones that compose living
cells; many of the drugs used to control diseases and
relieve suffering; the perfumes and colors of the plants
world; and thousands of substances that participate in the
metabolic activities of living things. With planning this
syllabus the following considerations were taken into
account :
1-
In order to understand biological phenomena at the molecular
level , particularly the metabolic pathways by which
materials are interconverted in cells , they need to know
the reactions of the functional groups which are present in
molecules occurring in nature and also the mechanisms of
reactions to get the bases of rationalisation the industrial
and biological processes . Since the nature of the reaction
of functional groups depend on the electronic structure of
the groups accounts of chemical reactivity are prefaced by
electronegativity of elements which is the base of many
organic molecules properties, bonds energies and a survey of
chemical bonding in which emphasis is placed on covalent
bonding and by an account of some general aspects of
chemical reactions.
2-
Stereochemistry a topic which is of great importance in any
account of biochemical reactions. In our opinion it is
important to provide a logical connection between the
laboratory reactions of the Organic Chemistry and its
counterpart in a living cell.
3-
Also the most important methods of synthesis of simple
organic compounds were highlighted in this syllabus to give
an idea that there is no limit to the number of organic
compounds that can be made, and indeed the known synthetic
compounds include many naturally occuring compounds that
have been prepared synthetically as final confirmation of
their structures.
4-
The physical methods used in Organic Chemistry ( such as
elemental analysis , UV/VIS , IR , NMR , MS ) were included
as they are very important for students of pharmacy to
identify and characterise carbon compounds .
5-
The heterocyclic compounds were given more considerations as
they are representing the most of pharmaceutical compounds
with biological significance.
1. Introduction to Organic
Compounds:
-
Classification of Carbon
Compounds:
Aliphatic compounds, Alicyclic compounds, Aromatic
compounds, Heterocyclic compounds.
-
The Structures and
Nomenclature of Functional Groups
-
Bonding in Organic
Compounds: Covalent Bonding, Co-ordinate Bonding, Ionic
Bonding in Organic Compounds, and the Hydrogen Bond.
-
Structure and Physical
Properties of Organic Compounds: Bond Dissociation
Energy, Polarity of Bonds, Polarity of Molecules,
Melting Points,
-
Intermolecular Forces
(Dipole-Dipole Interactions, Hydrogen Bonds, and Van Der
Waals Forces), Boiling Point , and Solubility.
-
Acids and Bases: The Lowry-Bronsted
Definition, and the Lewis Definition
-
Hybridisation of Atomic
Orbitals of Carbon: Carbon Atom in the Ground State and
in the Excited State, SP3-Hybridisation,
SP2-Hybridisation, SP-Hybridisation, the Formation of
single, double, and triple Bonds between Carbon Atoms,
the Structure of NH3 and H2O ( SP3-Hybridisation).
2. Isomerism:
Introduction and Definition,
Structural Isomerism (Definition, Chain Isomerism, Position
Isomerism, Functional
Isomerism, Metamerism, and Tautomerism). Stereoisomerism or
Stereochemistry (Definition, Tetrahedral Carbon Atom,
Optical Isomerism, Polarised light, Optical activity,
Specific optical rotation, Polarimeter, Chirality,
Enantiomerism, Racemisation (Definition, Racemic
modifications preparation, and Resolution of racemic
modifications), Diastereomerism, Geometric Isomerism (cis-
and trans-isomers), Z / E isomerism, Meso Compounds,
Relative and Absolute Configurations (Definition, Relative
Configurations D- and L-, Absolute Configurations R- and
S-), Number of Stereoisomers, Representation of
Configuration of Enantiomers (Fisccher’s Projection,
Newmann’s Projection, Wedge Projection, and Sawhorse
Projection Formulas), Elements of Symmetry (Plane and Centre
of Symmetry), Optical Isomerism without Asymmetric Atom.
3. Conformational Isomerism of
Alkanes:
Definition, Staggered,
Eclipsed, and Gauche Conformers, Factors influencing the
Conformational Stability (Torsional Strain, Steric Strain
due to Van Der Waals Forces,
Dipole-dipole Interaction).
4. Cyclic Aliphatic
Hydrocarbons (Cycloalkanes):
Definition, Nomenclature,
Conformations of Cycloalkanes and their Stabilities, Factors
influencing stability of
conformation (Angle Strain, Torsional Strain, Steric Strain,
Dipole
-dipole interactions),
Conformations of Cyclohexane (Chair Conformation, and Boat
Conformation), Equatorial and Axial Bonds in Cyclohexane,
1,3-Diaxial interactions in
substituted Cyclohexane,
Stereoisomerism in Cyclic Compounds (cis- and
trans-isomers),
Enantiomers
in Cyclic Compounds.
5.Chemical Reactions:
General aspects of Chemical
Reactions, Reaction Mechanism, Classification of Organic
Reactions (Substitution,
Elimination, Addition to Multiple Bonds, Molecular
Rearrangements), Classification of Organic Reagents (Nucleophiles,
Electrophiles, and
Free Radicals), Charge
Distribution in Organic Molecules and Electronegativity,
Inductive
Effect, Mesomeric Effect and
-Electron Delocalisation and Resonance.
6. Energy Changes During
Reactions:
Bond Dissociation Energy, Heat
of Reaction, Energy of Activation, Transition State,
Progress of Reaction
(Exothermic and Endothermic Reaction).
7. Aliphatic Nucleophilic
Substitution Reactions:
Definition, the Relationship
between Nucleophilicity and Basicity, the SN2 Mechanism, the
SN1 Mechanism, the Factors
Favouring either SN2 or SN1 Reactions, Energetics of SN1 and
SN2 Reactions, Stereochemistry
of SN1 and SN2 Reactions, Mixed SN1 and SN2 Mechanisms,
Transition between SN1 and SN2
Mechanisms, Factors influencing the Course of
Substitution Reactions (Nature
of the substrate, Nature of the Solvent, Nature of the
Nucleophile,
Nature of the Leaving Group, the Neighbouring Group
Participation).
8. Elimination Reactions:
-Elimination, -Elimination
or 1,2-Elimination (Dehydrogenation, Dehydration,
Dehalogenation,
and Dehydrohalogenation), E1 and E2 Mechanisms, Competition
between
E2 and SN2 Reactions, E1cB
Eliminations, Orientation of Double Bond.
9. Alkylation:
Definition, Perkin’s Reaction,
Knoevenagel’s Reaction, Stobbe’s Condensation, Michael’s
Addition Reaction,
Cyanoethylation, Mannich’s Reaction, Reformatsky’s Reaction.
10. Molecular Rearrangements:
Definition, Pinacol’s
rearrangement, Wanger-Meerwein’s rearrangement, Wolff
rearrangement, Hofmann’s rearrangement, Lossen’s
rearrangement, Beckmann’s rearrangement, Claisen’s
rearrangement, Allylic rearrangement, Favorskii’s
rearrangement, Orton’s rearrangement.
11. Free Radical Reactions:
Definition, Generation of
Stable Free Radicals, Generation of Short-lived Free
Radicals,
Radical Coupling Reactions,
Types of Free Radical Reactions (Radical Displacement,
Radical Addition, Radical
Substitution in Aromatic Systems).
12. Alkanes (Paraffinic
Hydrocarbons):
Definition and Nomenclature,
Structural Isomerism, Nomenclature of Functional groups,
General methods of preparation,
Naturally occurring Alkanes, Properties of Alkanes,
General Reactivity,
Halogenation, Oxidation, Dehydrogenation, Nitration, and
Sulphonation
of Alkanes.
13. Alkenes - Double Bond (Olifinic
Hydrocarbons):
Definition, Nomenclature,
Compounds of Biological interest which contain Double Bonds,
General methods of preparation, Properties of Alkenes,
General reactivity (Addition of Halogens, Addition of water
and related compounds, Oxidation-Reduction of the Double
Bond, Addition reactions to the substituted Double Bond and
Markovnikov’s Rule).
14. Dienes:
Commulative
Dienes (Synthesis and Reactions), Isolated Dienes (Synthesis
and
Reactions), Conjugated Dienes
(Synthesis and Reactions).
15. Alkynes:
Definition and Nomenclature,
General methods of preparation, Reactions of Alkynes.
16. Benzenoids:
Definition, Structure of
Benzene and Resonance Theory, Aromatic Character,
Nomenclature of Benzene
Derivatives, Electrophilic Aromatic Substitution (Electrophilic
Substitution reactions
mechanism, Halogenation, Nitration, Sulphonation, Friedel-Craft’s
Alkylation,
Friedel-Crafts Acylation), Effect of substituents on
disustitution of Benzene,
Effect of substituent on
orientation (o- , m- , p- ), Effect of Substituent on
Reactivity,
Theory of Relative Reactivity
and Orientation (The Effects of induction effect I, and
Mesomeric
effect M), Ortho-Para Directing groups with +I Effect,
Ortho-Para Directing
groups having -I and +M
Effects, Meta-Directing groups, Effect of Halogens
(Ortho-Para
Directing groups but deactivate
the Benzene Ring), Ortho-Para ratio in the formation of
disubstitution
derivatives, Introduction of a third substituent into the
Benzene Ring,
Importance of orientation and
reactivity in synthesis, Aliphatic-Aromatic Hydrocarbons (Arenes),
General methods of prepration of Alkylbenzenes Friedel-Craft’s
Alkylation, Friedel-Craft’s Acylation followed by reduction,
Wurtz-Fitting reaction), Physical properties of
Alkylbenzenes, Chemical properties of Alkylbenzenes
(Substitution reactions of the Benzene Ring such as
Halogenation, Nitration, Sulphonation, Friede -Crafts
Reactions), Substitution reactions of the Alkyl Side Chains
such as Halogenation (Free Radical Reaction), Hydrogenation,
Oxidation, Aromatic Nucleophilic substitution, Factors
affecting Nucleophilic Substitution (Structure of Substrate,
Effect of leaving group, Effect of attacking group).
17. Alkyl Halides:
Definition, Nomenclature(
Common and IUPAC Systems ), Methods of Preparation,
Physical Properties, Chemical
Properties ( Nucleophilic Substitution Reactions SN – such
as Replacement of Halogen by Hydroxyl Group, Alkoxy Group,
Cyano Group, Carboxyl Group, Amino Group, Hydrosulphide
Group, Mercaptide Group, Alkyyl and Aryl Group, Elimination
Reactions( E1 and E2 Mechanisms ), Reduction of Alkyl
Halides, Formation of Grignard Reagents, Unsaturated Halogen
Compounds - such as Vinyl and Aryl Halides and their Low
Reactivity, Allylic Halides, Polyhalogen Compounds- such as
Chloroform, Carbon Tetrachloride, Their Synthesis and
Reactions.
18. Alcohols:
Definitions, Classification,
Nomenclature (Common and IUPAC Systems), General methods of
preparation, Physical properties and the Hydrogen Bonding,
Chemical properties: Reactions involving the cleavage of
O--H Bond (such as reaction with Metals, Reaction with
Grignard reagents, Reactions with Organic Acids, Reactions
with Acid Halides or Acid Anhydrides), Reactions involving
the cleavage of C--OH Bond (such as reactions with Hydrogen
Halides, Reactions with phosphorus halides and reaction with
Thionyl Chloride), Reactions involving both Alkyl and
Hydroxyl Groups (such as Dehydration, Oxidation of Primary,
Secondary, and Tertiary Alcohols).
19. Ethers:
Definitions, Nomenclature
(Common and IUPAC Systems), General methods of Preparation,
Physical properties, Chemical properties (Formation of
Oxonium Salts, Formation of Peroxides, Cleavage by Acids
such as HBr and HCl Through SN1 or SN2 Mechanisms,
Electrophilic Substitution in Aromatic Ethers).
20. Aldehydes and Ketones:
Structure of Carbonyl group and
Definition of Aldehydes and Ketones, Nomenclature of
Aldehydes and Ketones (Common and IUPAC Systems), Methods of
Aldehydes and Ketones preparation, Physical properties of
Aldehydes and Ketones, Chemical properties of Aldehydes and
Ketones (Reactivity of Carbonyl group towards Nucleophilic
attack, Role of Acid catalysis in Nucleophilic Reactions,
Acidity of -Hydrogens, Nucleophilic addition reactions
such as addition of Sodium Bisulphate, Addition of Ammonia
derivatives such as NH2NH2, NH2NHC6H5, NH2NHCONH2 and semi-carbazide,
Addition of Alcohols, Addition of Hydrogen Cyanide, Addition
of Grignard reagents, Reformatsky reaction, Aldol
condensations, Base promoted Halogenation, Acid Catalysed
Halogenation,Oxidation of Aldehydes and Ketones, Reduction
reactions.
21. Carboxylic Acids:
Definitions and Structure of
Carboxyl group, Nomenclature (Common and IUPAC Systems),
General methods of preparation, Physical properties and the
Hydrogen Bonding, Chemical properties (Reactions due to the
Ionisable Hydrogen - such as Acidity and Salt formation,
Reactions involving replacement of Hydroxyl group such as
Formation of Esters, Formation of Acid Chlorides, Formation
of Amides, and Formation of Anhydrides, Decarboxylation,
Reactions of the Alkyl or Aryl groups, Aromatic Carboxylic
Acid Substitution, Acidity Constants of Carboxylic Acids,
Effect of Substituents on Acidities of Carboxylic Acids .
22. Amines:
Definition, Classification,
Nomenclature,General Methods of Preparation, Physical
Properties, Chemical Properties( Basicity and Salt
Formation, Alkylation, Conversion into Amides, Reaction with
Nitrous Acid, Ring Substitution in Aromatic Amines, Basicity
of Amines, Effect of Substituents on the Basicity of
Aromatic Amines, Exhaustive Methylation of Amines and
Hofmann Elimination, Cope Elimination ) .
Practical Course in Organic
Chemistry - 2-nd Year
1- Introduction to practical
course in Organic Chemistry.
A- Rules of work in laboratory
of Organic Chemistry :
General rules, rules of work
with acids and bases, works with explosive , inflammable ,
and toxic substances, offering the first aid in cases such
as burn., extinguishing of fire and burning clothes in the
laboratory .
B- Glassware used in practical
Organic Chemistry .
naming of glassware , cleansing
and drying glassware , labeling and storage of samples .
2- The Basic Physical Methods
Used in Organic Chemistry .
A- Determination of some
physical constants :
melting point , boiling point,
refractive index, optical rotation, density,
crystallization, sublimation, distillation, extraction
B- Chromatography methods :
gas-adsorption chromatography,
high pressure liquid chromatography, thin layer
chromatography, column chromatography, paper chromatography
II) PHARMACEUTICAL ANALYTICAL
CHEMISTRY-I:
Contents:
A) Theoretical Part:
Qualitative Analysis
1- Anion analysis:
Carbonate,
bicarbonate and their mixtures, Sulphur salts and mixtures,
Halides and mixtures, arsenic, phosphoric acid salts and
mixtures, Nitrate and nitrite salts and mixtures, Cyanogen
salts and mixtures.
2- Cation analysis:
Silver group
(single and in unknown mixtures), Copper-Arsenic group
(single and in unknown mixtures), Iron group (single and in
unknown mixtures), Zinc group (single and in unknown
mixtures), Alkaline-earth group (single and in unknown
mixtures), Alkali and magnesium group (single and in unknown
mixtures).
3-Difficultes in cation
analysis:
Insolubles,
Phosphate, Organic matter, Oxidizing agent.
3) Complexometic Titrations:
General
considerations, Titration of metal ions with ligands,
Indicators, Applications.
4) Preciptimetry:
Theory of
preciptimetry, Titration curves and end point detection,
Application.
5) Gravimetry:
Analytical
separations, Colloidial properties, Theory of precipitation
process, Purity of precipitates, Organic precipitates,
Applications.
III)
PHARMACEUTICS-I
:
Contents:
A) Theoretical Part:
1- The prescription:
Definition,
Parts of prescription, Calculation of the dose,
Pharmaceutical Latin, Dispensing of the prescription, Some
legal aspects in pharmacy, Labeling.
2- Pharmaceutical systems
and techniques of measurement:
The metric
system, The apothecary system, Intersystem conversion,
Common household measures, Density and specific gravity,
Dilution and concentration.
3- Extraction and
extractives:
Infusion,
decoction, digestion and maceration, Percolation method,
Tinctures, liquid extracts and other extractives.
4- Pharmaceutical solution
dosage forms:
Aqueous
solutions, waters, douches, enema, gargles and lotions,
Syrups, Coloring and flavoring agents, Non-aqueous
solutions.
5- Ophthalmic preparations:
Anatomy and
physiology of the eye, Ophthalmic solutions: sterility and
preservation, isotonicity, buffering, viscosity and
thickening agents, packaging; Ophthalmic suspensions,
Ophthalmic ointments, Ophthalmic inserts.
6- Parenteral solutions:
Vehicles and
excipients used in the formulation of parentrals,
Isotonicity, Sterilization of parentrals, Quality control of
parentrals.
7- Surface active agents and
solubilization:
Interfacial
and surface phenomena, Classification of surface active
agents, HLB system, Solubilization and its applications.
8- Adsorption phenomena:
Adsorption
at the solid/liquid interface, Mechanism of adsorption,
Adsorption isotherms, Factors affecting adsorption process,
Application in pharmacy.
9- Complexation:
Definition,
Classification, Application and analysis.
10- Reaction Kinetics and
drug stability:
Rate and
order of reactions, Determination of the order of reaction,
Factors affecting reaction rate, Accelerated stability
testing, Decomposition pathways, Stabilization of medicinal
agents.
B) HISTORY OF PHARMACY (In
Arabic)
C) Practical Part:
1- Preparation of aromatic
waters:
Peppermint
water, Chloroform water, Cherry laurral water
2- Preparation of simple syrup
3- Tutorials for
calculations and problems
Metric
system, Apothecary system, Interconversions, Dilutions and
concentrations.
4- Mixtures:
Simple
soluble mixture, Mixtures using infusion, Mixtures using
decoction, Mixtures containing extracts and tinctures.
5- Tutorials for tonicity
and buffer calculations:
Different
methods of isotonicity calculation, Different methods of
different buffers ratio and buffer capacity calculations.
6- Preparation of parenteral
solutions
7- Preparation of ophthalmic
solutions
8- Measurement of surface
tension and CMC
9- Adsorption experiments
10- Solubilization phase
diagram
11- Hydrolysis of ethyl acetate
kinetics in acid medium
12- Hydrolysis of ethyl acetate
kinetics in alkaline medium
IV) BOTANY AND MEDICINAL
PLANTS:
Contents:
A) Theoretical Part:
1- Plant morphology and
anatomy:
Seed and
seedlings, Cell and cell contents, Morphology of different
plant organs, Types of plant tissues, Primary structure of
plant organs, Secondary structure in stem and root.
2- Plant kingdom and plant
taxonomy:
Viruses,
Bacteria, Algae, Fungi, Bryophytes, Pteridophytea
gymnosperms.
An introduction to plant
taxonomy including flower morphology, Terminology and
nomenclature, Inflorescences, Fruits, Taxonomic description
of some monocot and dicot families with special reference to
some medicinal plants.
3- Plant physiology:
Colloidal
systems, Chemical and physical properties of the protoplasm.
Osmosis : osmotic potential ,
plant-water relations.
Mineral nutrition.
Enzymes: properties,
specificity, classification., Metabolism, anabolism,
catabolism, energy metabolism, respiration and
photosynthesis., Growth and differentiation.
B) Practical Part:
Selected experiments on the
above topics.
V) ANATOMY:
Contents:
1- Introduction:
The
organization of the human body, systemic and regional
introduction to the major organ I systems, descriptive
terms; terms related to position and movement.
2- The locomotor system:
Components,
structure of bone, morphological and gross structural
classification of bone, functions of bone, the axial and
appendicular skeletone, definition and classification of
joints, amphiarthordal and diarthroidal joints, types of
muscle, morphology of skeletal muscles, major groups of
skeleta muscles of head and neck, limbs and trunk.
3- The cardiovascular
system:
The
circulation, the surface markings, interior and blood and
nerve supply of the heart, major arteries and their
distribution, systemic and portal veins, lymphatic drainage
and main groups of lymph nodes.
4- The respiratory system:
The nasal
cavity, pharynx, larynx, trachea and bronchi, lungs and
pleura.
5- The digestive system:
The mouth
cavity, pharynx, oesophagus, stomach, intestines, the
associated glandsliver and spleen.
6- The renal system:
The kidnys,
ureters, urinary bladder and urethra.
7- The reproductive system:
The male and
female gonads, internal duct system and external genitalia.
8- The neuro-endocrine
system:
The
hypophysis cerebri, thyroid, parathyroid, thymus and adrenal
glands, the somatic nervous system; spinal cord and
formation of spinal nerve, the brain stem and cerebral
hemisheres, cranial and spinal nerves, the autonomic nervous
system.
9- The integument:
VI) HISTOLOGY:
Contents:
I) Cytology:
1- Nucleus.
2- Cytoplasm:
Cell
organelles : (plasma membrane - Golgi complex - mitochondria
- endoplasmic reticulum - lysosomes - ribosomes - centrosome
- microtubules - filaments).
Cell inclusions : (stored food
- pigments). Cilia - microvilli and junction between the
cells.
II) Basic tissues:
The epithelial tissue: (simple
- stratified - glandular and neuro - epithelium). The
connective tissue: (connective tissue proper - cartilage -
bone). The muscular tissue: (skeletal muscle fibers- cardiac
muscle fibers- smooth muscle fibers). The nervous tissue:
(neuron - nerve fibers - nerve trunk and ganglia).
III) The blood:
(Red blood corpuscles - white
blood corpuscles and blood platelets).
IV) Systemic Histology:
The Aorta, Spleen and lymph
node, Trachea and lung , Liver and pancreas, Stomach fundus
and small intestine , Kidney, Testis ,Ovary
,Pituitary gland - Thyroid gland
10- Spinal cord (corvical
region)
VII) HHUMAN CLINICAL
PHYSIOLOGY:
Contents:
A) Theoretical Part:
1- General survey:
Definitions and terminology,
External and internal environments, Homeostasis and outlines
of control systems.
2- Cell:
Cell functions, Cell membrane
and transport, Nerve and muscle, Neuromuscular transmission.
3- Blood:
General function of blood,
Functions of plasma proteins, Homeostasis (mechanism and
disorders); Red blood cells (functions, factors affecting
erythropoiesis, anaemia, polyceythaemia); Blood groups (A,
B, O and Rh systems); White blood cells (functions,
lymphatic tissue and immunity, allergy); Interferons; Blood
volume and regulation of water balance.
4- Autonomic nervous system:
General functions, Organisation,
Division, Autoregulation of various organs and systems,
Autonomic reflexes, Neurotransmitters.
Ganglia, types, functions,
outflow, receptors.
5- Cardiovascular system:
Dynamics and functions of
cardiac muscle, Cardiac cycle - E.C.G. - heart sounds -
jagular venous pulse curve, Work of the heart, Heart rate
and venous return and their regulations, Cardiac output and
its regulation, Arterial blood pressure and its regulation,
Special circulation (coronary - pulmonary - hepatic -
cutaneous - cerebral - lymphatic - neonatal), Effects on
circulation by: (exercise - haemorrhage - shock - anaemia),
Oedaema.
6-Respiratory system:
External and internal
respiration, Intrapleural and intrapulmonary pressures,
Exchange of gases, Dead space, Volumes and capacities of
respiration, Oxygen dissociation curve, Chloride - Shift
phenomenon, Regulation of respiration: (central and
peripheral), Apnoea - hyperpnoea - tachypnoea – dyspnoea,
Cough – sneezing, Respiratory neonate, Cyanosis and hypoxia,
Artificial respiration.
7- Digestive system:
Salivary glands: (types -
functions and control), Chewing, swallowing and control, Gut
movements and secretions: (neutral and chemical control),
Gut contents, Vomiting, Defaecation and diarrhea, Pancreas,
liver, bile and jaundice.
8-Metabolism:
Metabolic rate and B.M.R, R.Q.
and excess R.Q, Specific dynamic action, Heat control and
its disorders.
B) Practical Part:
Selected experiments on the
above topics.
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