36
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36.1
36.2
36.3
36.4
36.5
36.6
1
1
Drugs
Introduction
Development of Aspirin and cis-Platin
Key Stages of Drug Development
Over-the-Counter Drugs and Prescription
Drugs
Narcotics and their Adverse Effects
Stimulants and their Adverse Effects
New Way Chemistry for Hong Kong A-Level Book 3A
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36.1
Introduction
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New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Medicines and Drugs
•
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Medicines
 used to cure and prevent diseases
•
Drugs
 alter the way that our body
functions
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New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Medicines and Drugs
•
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Most medicines contain drugs
 but some drugs are not medicines
•
Example:
Alcohol and nicotine are not medicines
but they are drugs
•
4
4
Some drugs may or may not be
medicines depending on one’s state of
health
New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Drugs Derived from Folk Remedies
•
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Since ancient times
 man has used natural materials to
relieve pains, heal injuries and cure
diseases
•
5
5
Many of these folk remedies have been
shown to be very effective
New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Drugs Derived from Folk Remedies
•
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With latest scientific and technological
advancement
 active ingredients of folk remedies
have been isolated (e.g. by
chromatography) from the
natural medicines
 their structures are identified(e.g.
by M.S. or IR)
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New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Drugs Derived from Folk Remedies
•
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Example:
Morphine – extracted from the poppy
Papaver somniferum
•
Morphine
 powerful painkiller
 unless used carefully, morphine
can be harmful to our bodies
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New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
http://www.poppies.org/gallery/
Drugs Derived from Folk Remedies
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Poppies provide morphine
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New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Drugs Derived from Folk Remedies
•
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Example:
Salicylic acid – isolated from willow
bark
•
Salicylic acid
 the precursor of aspirin
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New Way Chemistry for Hong Kong A-Level Book 3A
36.1 Introduction (SB p.190)
Drugs Derived from Folk Remedies
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Willow bark contains salicylic acid,
which is the precursor of aspirin
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New Way Chemistry for Hong Kong A-Level Book 3A
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36.2
Development of
Aspirin and
cis-Platin
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
•
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For a long time, the bark of the willow
tree (salix alba)
 used as a traditional medicine
 relieve the symptom of fever
•
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12
http://en.wikipedia.org/wiki/Aspirin
New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
•
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In the 1860s, chemists showed
 salicylic acid (2-hydroxybenzoic acid)
in willow bark
COOH
 as active ingredient
OH
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
•
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By 1870, salicylic acid was widely
used as
 painkiller (analgesic)
 fever depressant (antipyretic)
 anti-inflammatory medication
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
•
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The undesirable side effects of
salicylic acid
1. irritating and damaging the lining
of the mouth and stomach
2. causing allergy to some people
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
•
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Molecular modification is necessary
 give a derivative
 effective as salicylic acid but has
less undesirable side effects
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
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(a)
(b)
Structures of (a) salicylic acid; (b) aspirin
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
In 1897
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Acetylation of salicylic acid to produce aspirin
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New Way Chemistry for Hong Kong A-Level Book 3A
Aspirin is a common over-the-counter drug.
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Prescription drugs – prescribed by doctors
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
Aspirin
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Aspirin is only slightly soluble in water.
Suggest how you can prepare a water-soluble
‘aspirin’.
COO -Na +
COOH
O
Na
O
O
O
NaOH, NaHCO3 not suitable ∵ hydrolysis
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.191)
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Example 36-2
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.192)
Aspirin
•
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At present, aspirin is still widely used in
the world
35000 tonnes of aspirin are produced
annually (each tablet has 300 mg aspirin)
Calculate the total number of aspirin
tablets produced per year.
1.17  1011
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.192)
Aspirin
•
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Recent researches have shown that
small daily doses of aspirin may help
prevent diseases
Anti-platelet(薄血丸)
 such as heart attack, stroke, and
the blindness and kidney damage
suffered by many patients with
diabetes
Check Point 36-2
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
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http://en.wikipedia.org/wiki/Cisplatin
•
In 1964, the biophysicist, Barnett
Rosenberg and his research group were
studying the effect of an electric field
on the growth of bacteria
 A platinum-containing substance
extracted from the bacterial culture
inhibited cell division
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
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square planar
cis-diamminedichloroplatinum(II)
[Pt(NH3)2Cl2]
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
•
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cis-platin alters the DNA of the cancer
cell
 when the cell tries to replicate, its
DNA cannot be copied correctly
 the cell dies
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
•
•
27
27
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The geometry of cis-platin is important
to its action
The geometrical isomer of cis-platin,
trans-platin, was ineffective in treating
cancer
New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
trans-Platin
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Structure of trans-platin. It is
ineffective in treating cancer.
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
•
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Tests on animals conducted to
investigate
1.
how this compound affects cell
division in mammalian cells
2. toxic side effects
3. different dose levels
 Clinical tests on patients
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
•
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The most severe side effects:
 nausea
 vomiting
 toxicity to the kidney
 toxicity to the bone marrow
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.193)
cis-Platin
Used in chemotherapy
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The use of cis-platin as an
anticancer agent
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New Way Chemistry for Hong Kong A-Level Book 3A
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36.3
Key Stages of
Drug Development
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.194)
Key Stages of Drug Development
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1. Lead compound(導引化合物) discovery
2. Molecular modification
3. Safety tests and human trials
4. Formulation(配方) development
5. Approval for marketing
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
preclinical
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The process of
drug testing
and approval
for human use
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.194)
Lead compound discovery
•
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Lead compound
 a compound with some desired
biological activities
 can be characterized and modified
to produce other compounds with
better therapeutic effects but less
unwanted side effects
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.194)
Lead compound discovery
•
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Development of lead compound
1. Understand how the body functions
at molecular levels both normally and
abnormally
2. Identify the drug target responsible
for a specific disease
3. Develop the lead compound with
therapeutic actions on the drug target
36
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.194)
Lead compound discovery
•
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Computer programs can be used to
facilitate the design of chemical
structures that are effective
Combinatorial Chemistry : involves the rapid synthesis or
the computer simulation of a large number of different
but structurally related molecules or materials
•
37
37
Hundreds of thousands of compounds
are screened to find out the lead
compound which shows most desirable
effects.
New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
Molecular modification
•
•
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The lead compound may have
undesirable side effects
Researchers need to modify the
molecular structure of the lead
compound
 improve its performance
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
Safety Tests and Human Trials
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1. Pre-clinical Research
•
Once the lead compounds have been
identified and modified
•
Using cell cultures in a petri dish
 to determine the effectiveness of
compounds
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
1. Pre-clinical Research
•
•
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The most effective compounds are then
subject to animal assays
Both short-term and long-term testing
are conducted on animals
to investigate the mechanisms, toxicity
and adverse side effects
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
2. Clinical Research
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(a) Phase 1
•
The first time that the drug is tested
on humans
•
Generally, 20 to 80 healthy volunteers,
 but sometimes patients are involved
in this phase of research
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
2. Clinical Research
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(a) Phase 1
To investigate
the metabolism, the structure-reactivity
relationships, the mechanism of action
and the side effects of the drug in
humans
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
2. Clinical Research
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(a) Phase 2
•
The purpose of phase 2 clinical
research is to determine
 the effectiveness of the drug to
treat patients with a specific
disease or condition
 common short-term side effects or
risks
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
2. Clinical Research
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(a) Phase 2
•
These studies are conducted on a larger
scale than the phase 1 studies
 several hundreds of patients are
involved
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
2. Clinical Research
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(a) Phase 3
•
Phase 3 clinical research aims to
 provide more information about the
effectiveness and the safety of the
drug
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45
 a still greater no. of patients are
involved to allow scientists to
extrapolate the results of clinical
research to the general population
New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
Formulation Development
•
•
46
46
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There are various routes of
administration of a drug
Each route requires different types of
formulation
New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
Formulation Development
•
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For oral route
 the drug can be in the form of
tablets, capsules or liquid
•
For parenteral(非口服的) route
 it can be in ampoules(針劑) or
intravenous fluid(靜脈注射液)
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.195)
Formulation Development
•
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Researchers have to find out
 which formulation of the drug brings
the greatest effect
 is the most suitable to the patients
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
•
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When the drug has passed all the phases
of the clinical research
 the pharmaceutical company of the
drug needs to make a formal
application to the regulatory
authority (like Food and Drug
Administration in the US) for
approving
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
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•
The application must include
 a description of how the drug was
manufactured
 results and analyses from the tests
of the drug on both animals and
humans
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
•
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The application must provide sufficient
information for the regulatory authority
to make several critical decisions:
 whether the drug is safe and
effective
 whether its benefits outweigh its
risks
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
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 whether the drug’s labelling
information is appropriate
 whether the manufacturing methods
used to make the drug are adequate
for ensuring the purity and integrity
of the drug
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
•
•
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Phase 4 clinical research is done after
the drug has been approved to be sold
in the market
The main purposes of phase 4 are to
find
 more about the side effects and
safety of the drug
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
•
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The main purposes of phase 4 are to find
 what the long-term risks and
benefits are
 how well the drug works when it is
used more widely than in clinical
research
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New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.196)
Approval for Marketing
•
•
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The process of developing and testing
a new drug is a lengthy one
it takes about 10 years to develop a
drug at a cost of 1 billion US dollars
Check Point 36-3
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New Way Chemistry for Hong Kong A-Level Book 3A
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7B
36.4
Over-the-Counter
Drugs and
Prescription Drugs
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.197)
Over-the-Counter Drugs and
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Prescription
Drugs
•
Drugs can be divided into two categories
based on how they can be bought
 Over-the-counter (non-prescription)
drugs
 Prescription drugs
Check Point 36-4
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.197)
Structure and uses of some common over-the-counter drugs
Structure
Uses
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Name
Aspirin
(e.g. Cortal)
• As analgesics and
antipyretics
Acetaminophen
(e.g. Panadol)
• As analgesics and
antipyretics
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New Way Chemistry for Hong Kong A-Level Book 3A
OH
Aspirin
1
O
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Analgesics and antipyretics
2
O
O
CH3
2-(acetyloxy)benzoic acid
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New Way Chemistry for Hong Kong A-Level Book 3A
1
HO
NH
CH3
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O
Acetaminophen
4
Analgesics and antipyretics
N-(4-hydroxyphenyl)acetamide
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.197)
Structure and uses of some common over-the-counter drugs
Structure
Uses
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Name
Vitamin C
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• Helps maintain
elasticity of the skin,
aids the absorption of
iron and improves
resistance to infection
• Essential for the
formation of collagen
and intercellular
material, bone and
teeth and for healing of
wounds
New Way Chemistry for Hong Kong A-Level Book 3A
Vitamin C
OH
3
Helps maintain elasticity of
4
O
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the skin, aids the absorption
5 O
of iron and improves
1
1
resistance to infection.
HO
HO
2
2
HO
5-(1,2-dihydroxyethyl)-3,4-dihydroxyfuran-2(5H)-one
O
O
furan
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62
O
furan-2(3H)-one
O
O
furan-2(5H)-one
New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.198)
Structure and uses of some common prescription drugs
Structure
Uses
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Name
Albuterol
• For treating asthma,
emphysema(肺氣腫)
and chronic bronchitis
• Dilates the bronchial
airways by relaxing the
surrounding muscles
Amoldipine
• As an anti-hypertensive
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Albuterol
CH3
Treating asthma, emphysema
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NH
H3C
CH3
and chronic bronchitis
2
HO
1
4
2
OH
1
OH
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.198)
Structure and uses of some common prescription drugs
Structure
Uses
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Name
Amoxicillin
(E.g. Augmentin)
• As an antibiotic used to
treat bacterial
infections
Omeprazole
• Suppresses secretion
of gastric acid
• Used for the treatment
of duodenal and gastric
ulcers and
gastroesophageal
reflux disease(胃酸倒
流病)
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.198)
Name
Structure
Uses
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• Relieves nasal and
Chlorpheniramine
(e.g. Coltalin,
Dristan)
Brompheniramine
(e.g. Neosed, 樂信)
Br
non-nasal symptoms of
common cold and
allergies (e.g. runny
nose, itchy eyes,
watery eyes, sneezing)
• As an antihistamine
Loratadine
(e.g. 幸福安泰敏)
- Ditto -
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New Way Chemistry for Hong Kong A-Level Book 3A
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Halogenated pheniramines are up to 20-fold
more potent than pheniramine
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36.5
Narcotics and their
Adverse Effects
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36.5 Narcotics and their Adverse (SB p.199)
Narcotic analgesics(麻醉鎮痛劑)
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Examples
:-
69
69
•
Morphine – pain relief
•
Heroin – no medical use
•
Methadone – treatment of narcotic
drug addiction
•
Opium – not medical use
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.199)
Narcotic analgesics(麻醉鎮痛劑)
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Unlike aspirin, narcotic analgesics
 produce euphoria, a feeling of
great happiness or well-being
 are addictive
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36.5 Narcotics and their Adverse (SB p.199)
Narcotic analgesics(麻醉鎮痛劑)
•
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Heroin and morphine are
 obtained by evaporating the sap of
the opium poppy
 generally called opiates
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New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.199)
Morphine and Heroin
•
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About 5000 years ago, the
Babylonians used crude opium to
relieve pains
•
The alkaloid morphine was first
isolated from the opium poppy
(Papaver somniferum) in 1803
•
Its addictive properties were known
from early times
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.199)
Morphine and Heroin
•
按一下以編輯母片標題樣式
In 1898, morphine was acetylated to
produce diacetylmorphine, or heroin
Glacial acetic acid
CH3COOH
Morphine
Heroin
More addictive
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New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.199)
Morphine and Heroin
•
按一下以編輯母片標題樣式
Morphine
 used in cases of acute and chronic
servere pain and on the battlefield
 50 times as potent as aspirin
Etorphine : 2000 times as potent as morphine
Org. Chem notes p.19
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36.5 Narcotics and their Adverse (SB p.199)
Morphine and Heroin
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morphine hydrochloride
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36.5 Narcotics and their Adverse (SB p.199)
Draw the structures of morphine hydrochloride
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H
CH 3
CH 3
N+Cl -
N
HCl
O
HO
O
OH
HO
OH
Why is morphine converted to morphine hydrochloride ?
To make it more soluble in water
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New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.199)
Morphine and Heroin
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heroin
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New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Adverse Effects of Use of
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Morphine
and Heroin

drowsiness

respiratory depression

nausea and vomiting

develop tolerance(耐藥性) and physical
dependence (心理依賴/成癮)
Tolerance : higher doses are needed to
produce the same effect
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New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Adverse Effects of Use of
按一下以編輯母片標題樣式
Morphine
and Heroin
Characteristics of dependence:
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
daily use

inability to stop usage

constant or repeated intoxication(中毒)

overdose

withdrawal symptoms(斷癮跡象)
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Withdrawal symptoms(斷癮跡象)
 按一下以編輯母片標題樣式
watery eyes
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
runny nose

yawning

loss of appetite

irritability(煩躁), tremors(震顫)

panic(驚惶), chills(感到寒冷)

sweating, cramps(痙攣)
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Adverse Effects of Use of
按一下以編輯母片標題樣式
Morphine
and Heroin
•
Unlike depressants (e.g. alcohol and
barbiturates(巴比妥酸鹽)),
they usually do not cause physical damage
to the brain, liver, or heart
•
Unlike stimulants,
they do not induce psychotic experiences
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New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Adverse Effects of Use of
按一下以編輯母片標題樣式
Morphine
and Heroin
•
Heroin abusers are prone to numerous
life-endangering conditions
 tend to neglect their health
 fail to detect common signs of
illness
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82
 frequently resort to intravenous
injection of opiates with shared
needles
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Adverse Effects of Use of
Morphine and Heroin
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Commonly observed problems:
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83

the transmission of HIV, AIDS, viral
hepatitis (hepatitis B virus)

inflammation of the heart’s lining(心膜)

blood poisoning

tetanus(破傷風),

malaria(瘧疾), syphilis(梅毒)
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
Adverse Effects of Use of
按一下以編輯母片標題樣式
Morphine
and Heroin
Commonly observed problems:
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84

blood vessel inflammation

heart valve(心瓣膜) infection

malnutrition

festering sores(膿瘡) on the arms and
legs

the toxic effects of overdose
New Way Chemistry for Hong Kong A-Level Book 3A
36.5 Narcotics and their Adverse (SB p.200)
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New government posters against drug abuse
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http://www.nd.gov.hk/en/antidrug_resources.htm
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36.6
Stimulants and their
Adverse Effects
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36.6 Stimulants and their Adverse Effects (SB p.200)
Stimulants(興奮劑)

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a drug that increases the activity of
various parts of our nervous system

provides us a temporary sense of
alertness and well-being as well as
relief from fatigue

can be used to boost endurance and
productivity as well as to suppress
appetite
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.200)
Examples of stimulants : -
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Amphetamine (Yaba, Ice)
Cocaine (crack, snow)
Ecstasy(搖頭丸/忘我/狂喜/E仔)
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.200)
Ketamine(氯胺酮)
•
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Not a stimulant
•
Also known as K, Ket, special K, or Kitty
•
Belongs to a class of drugs called
“dissociative(解離/人格分裂)anaesthetics”
A dissociative drug is one which reduces
(or blocks) signals to the conscious mind
from other parts of the brain
Dissociative disorder  解離症/人格分裂
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.200)
Ketamine(氯胺酮)
•
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First used on American soldiers during
the Vietnam War, but it is often
avoided now
 it can cause unpleasant out-of-body
experiences
•
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Still used widely in veterinary medicines,
and for certain human applications
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.201)
Ketamine(氯胺酮)
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Keto group
2o amine
*
* chiral centre
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New Way Chemistry for Hong Kong A-Level Book 3A
Ketamine(氯胺酮)
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C H ClNO
13
2
Cl
2-(2-chlorophenyl)
16
1
NH
2
1
CH3 2-(methylamino)
O
2-(2-chlorophenyl) -2-(methylamino) cyclohexanone
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.201)
Adverse Effects of Use of Ketamine
•
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At low doses
 causes an increase in heart rate
 gives a mild, dreamy feeling and
drowsiness
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.201)
Adverse Effects of Use of Ketamine
•
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At higher doses
 produce a hallucinogenic effect(幻覺)
 may cause the users to feel very far
away from their body
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95
 this effect is referred to as
entering a “K-Hole”, and has been
compared to a near death experience
with sensations of rising above one’s
body
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.201)
Adverse Effects of Use of Ketamine
•
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Frequent intake of ketamine can cause
 depression
 nausea
 impaired long-term memory and
cognitive difficulties
 impaired motor function, respiratory
and heart problems
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.201)
Adverse Effects of Use of Ketamine
•
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Frequent intake of ketamine can cause
 a tremendous physiological
/psychological dependence
 addiction
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36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
•
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Phenylethanamine (or 2-phenylethan-1amine) is an alkaloid and monoamine
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
•
Phenylethanamine
 believed to function as a
neurotransmitter in the human brain
 found in many food like chocolate
and is responsible for its effects on
mood, appetite and sense of wellbeing
Chocolate as a drug
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
•
Phenylethanamine
 may have psychoactive effects in
sufficient quantities, but quickly
metabolized in our body
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
•
Substituted Phenylethanamine
 a broad and diverse class of
compounds
 include hormones, stimulants,
hallucinogens(迷幻劑) and
antidepressants(抗鎮抑劑)
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
Amphetamine

a homologue of phenylethanamine

carrying an  methyl group
*
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
Amphetamine
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103

synthetic stimulant

used to suppress the appetite,
control weight and treat disorders
including narcolepsy(渴睡症) and
attention-deficit hyperactivity disorder
(ADHD)
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.202)
Phenylethanamine and
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Substituted
Phenylethanamines
Amphetamine
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
used recreationally and for
performance enhancement

these uses are illegal in most countries
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.203)
Adverse Effects of Use of Amphetamine
•
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The side effects:
 insomnia(失眠)
 Irritability(煩躁)
 loss of appetite
 hallucination(幻覺)
 heart and kidney failure
 tolerance
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.203)
Adverse Effects of Use of Amphetamine
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Chronic users of amphetamines:
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106

psychologically dependent on
amphetamines

chronic heavy users generally fail to
eat properly (Anorexia, 厭食症)

develop various illnesses related to
vitamin deficiencies and malnutrition
New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.203)
Adverse Effects of Use of Amphetamine
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Chronic users of amphetamines:
 more prone to illness
 develop mental disturbance known as
amphetamine psychosis(精神病)
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New Way Chemistry for Hong Kong A-Level Book 3A
36.6 Stimulants and their Adverse Effects (SB p.203)
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The END
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36.2 Development of Aspirin and cis-Platin (SB p.191)
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We do not want to rely on the natural products (like
willow trees) as medicines (like salicylic acid). Why?
Medicines which are “natural products” (e.g. those
which come directly from plants) may be difficult to
obtain when needed. The supply may be seasonal, may
depend on weather conditions and may be liable to
contamination. Collecting plants from their natural
habitat may cause harms to the environment.
Anise for Tamiflu
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36.2 Development of Aspirin and cis-Platin (SB p.192)
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At the end of the 19th century, the compound phenol was
already well-known in the pharmaceutical industry. Phenol
has germicidal properties. It was also readily available and
its molecular structure differs from that of 2-hydroxybenzoic
acid by only one functional group.
Phenol
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2-Hydroxybenzoic acid
New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.192)
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(a) What extra atoms have to be added to phenol to give
2-hydroxybenzoic acid?
(a) 1 carbon atom and 2 oxygen atoms
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New Way Chemistry for Hong Kong A-Level Book 3A
Answer
36.2 Development of Aspirin and cis-Platin (SB p.192)
Back
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(b) Suggest reagents and conditions necessary to bring about
the change from phenol to 2-hydroxybenzoic acid.
(b)
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112
Carbon dioxide can be combined directly with phenol toAnswer
give
2-hydroxybenzoic acid by careful control of the conditions. In an
alkaline medium, phenol is heated with carbon dioxide at 130°C
and under a pressure of 5 – 7 atm. Subsequent acid hydrolysis
yields salicylic acid. The reaction is known as the Kolbe-Schmitt
synthesis.
New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.192)
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Aspirin belongs to a class of organic compounds known as
esters. Esterification of salicylic acid with a reagent is used
to produce aspirin.
(a) Suggest reagents for converting salicylic acid to aspirin
in the esterification.
(a)
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113
Ethanoyl chloride and ethanoic
anhydride may be used.
New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.192)
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Aspirin belongs to a class of organic compounds known as
esters. Esterification of salicylic acid with a reagent is used
to produce aspirin.
(b) Write a chemical equation for the reaction involved.
Answer
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New Way Chemistry for Hong Kong A-Level Book 3A
36.2 Development of Aspirin and cis-Platin (SB p.192)
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(b)
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36.2 Development of Aspirin and cis-Platin (SB p.192)
Back
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(b)
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36.3 Key Stages of Drug Development (SB p.197)
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(a) What is the lead compound of aspirin?
(a)
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2-Hydroxybenzoic acid (or salicylic
acid)
New Way Chemistry for Hong Kong A-Level Book 3A
36.3 Key Stages of Drug Development (SB p.197)
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(b) Why is molecular modification of the lead compound
of aspirin necessary?
(b) It is because the lead compound of
aspirin has many undesirable effects.
It irritates and damages the lining of
the mouth and stomach.
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.199)
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cis-Platin is a prescription drug.
(a) What is the meaning of a prescription drug?
(a) A prescription drug means that the
use of the drug must be prescribed
by a medical doctor.
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New Way Chemistry for Hong Kong A-Level Book 3A
36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.199)
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cis-Platin is a prescription drug.
(b) Why is cis-platin regarded as a prescription drug?
(b) cis-Platin is a prescription drug because it
has numerous side effects on our health.
A professional decision from the medical
doctor is necessary for its adminstration.
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36.6 Stimulants and their Adverse Effects (SB p.201)
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Based on the structural formula of ketamine shown above,
answer the following questions:
(a) Give the molecular formula of ketamine.
Answer
(a) C13H16ClNO
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36.6 Stimulants and their Adverse Effects (SB p.201)
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Based on the structural formula of ketamine shown above,
answer the following questions:
(b) Name all the functional groups of ketamine.
(b) Amine (secondary), ketone, halobenzene, benzene ringAnswer
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36.6 Stimulants and their Adverse Effects (SB p.201)
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Based on the structural formula of ketamine shown above,
answer the following questions:
(c) Mark the chiral centre of ketamine in its structural
formula.
(c)
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36.6 Stimulants and their Adverse Effects (SB p.202)
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(a) Is amphetamine a primary, secondary or tertiary amine?
(a) A primary amine
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36.6 Stimulants and their Adverse Effects (SB p.202)
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(b) Mark the chiral centre of the molecule of amphetamine
in its structural formula.
(b)
(*chiral centre)
Amphetamine
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New Way Chemistry for Hong Kong A-Level Book 3A