36 按一下以編輯母片標題樣式 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 按一下以編輯母片標題樣式 36.1 Introduction 2 2 New Way Chemistry for Hong Kong A-Level Book 3A 36.1 Introduction (SB p.190) Medicines and Drugs • 按一下以編輯母片標題樣式 Medicines used to cure and prevent diseases • Drugs alter the way that our body functions 3 3 New Way Chemistry for Hong Kong A-Level Book 3A 36.1 Introduction (SB p.190) Medicines and Drugs • 按一下以編輯母片標題樣式 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 • 按一下以編輯母片標題樣式 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 • 按一下以編輯母片標題樣式 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) 6 6 New Way Chemistry for Hong Kong A-Level Book 3A 36.1 Introduction (SB p.190) Drugs Derived from Folk Remedies • 按一下以編輯母片標題樣式 Example: Morphine – extracted from the poppy Papaver somniferum • Morphine powerful painkiller unless used carefully, morphine can be harmful to our bodies 7 7 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 按一下以編輯母片標題樣式 Poppies provide morphine 8 8 New Way Chemistry for Hong Kong A-Level Book 3A 36.1 Introduction (SB p.190) Drugs Derived from Folk Remedies • 按一下以編輯母片標題樣式 Example: Salicylic acid – isolated from willow bark • Salicylic acid the precursor of aspirin 9 9 New Way Chemistry for Hong Kong A-Level Book 3A 36.1 Introduction (SB p.190) Drugs Derived from Folk Remedies 按一下以編輯母片標題樣式 Willow bark contains salicylic acid, which is the precursor of aspirin 10 10 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 36.2 Development of Aspirin and cis-Platin 11 11 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) Aspirin • 按一下以編輯母片標題樣式 For a long time, the bark of the willow tree (salix alba) used as a traditional medicine relieve the symptom of fever • 12 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 • 按一下以編輯母片標題樣式 In the 1860s, chemists showed salicylic acid (2-hydroxybenzoic acid) in willow bark COOH as active ingredient OH 13 13 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) Aspirin • 按一下以編輯母片標題樣式 By 1870, salicylic acid was widely used as painkiller (analgesic) fever depressant (antipyretic) anti-inflammatory medication 14 14 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) Aspirin • 按一下以編輯母片標題樣式 The undesirable side effects of salicylic acid 1. irritating and damaging the lining of the mouth and stomach 2. causing allergy to some people 15 15 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) Aspirin • 按一下以編輯母片標題樣式 Molecular modification is necessary give a derivative effective as salicylic acid but has less undesirable side effects 16 16 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) Aspirin 按一下以編輯母片標題樣式 (a) (b) Structures of (a) salicylic acid; (b) aspirin 17 17 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) In 1897 按一下以編輯母片標題樣式 Acetylation of salicylic acid to produce aspirin 18 18 New Way Chemistry for Hong Kong A-Level Book 3A Aspirin is a common over-the-counter drug. 按一下以編輯母片標題樣式 Prescription drugs – prescribed by doctors 19 19 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) Aspirin 按一下以編輯母片標題樣式 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 20 20 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) 按一下以編輯母片標題樣式 Example 36-2 21 21 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.192) Aspirin • 按一下以編輯母片標題樣式 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 22 22 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.192) Aspirin • 按一下以編輯母片標題樣式 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 23 23 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.193) cis-Platin 按一下以編輯母片標題樣式 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 24 24 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.193) cis-Platin 按一下以編輯母片標題樣式 square planar cis-diamminedichloroplatinum(II) [Pt(NH3)2Cl2] 25 25 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.193) cis-Platin • 按一下以編輯母片標題樣式 cis-platin alters the DNA of the cancer cell when the cell tries to replicate, its DNA cannot be copied correctly the cell dies 26 26 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 按一下以編輯母片標題樣式 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 按一下以編輯母片標題樣式 Structure of trans-platin. It is ineffective in treating cancer. 28 28 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.193) cis-Platin • 按一下以編輯母片標題樣式 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 29 29 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.193) cis-Platin • 按一下以編輯母片標題樣式 The most severe side effects: nausea vomiting toxicity to the kidney toxicity to the bone marrow 30 30 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 按一下以編輯母片標題樣式 The use of cis-platin as an anticancer agent 31 31 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 36.3 Key Stages of Drug Development 32 32 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 按一下以編輯母片標題樣式 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 33 33 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) preclinical 按一下以編輯母片標題樣式 The process of drug testing and approval for human use 34 34 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.194) Lead compound discovery • 按一下以編輯母片標題樣式 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 35 35 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.194) Lead compound discovery • 按一下以編輯母片標題樣式 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 36 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.194) Lead compound discovery • 按一下以編輯母片標題樣式 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 • • 按一下以編輯母片標題樣式 The lead compound may have undesirable side effects Researchers need to modify the molecular structure of the lead compound improve its performance 38 38 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 按一下以編輯母片標題樣式 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 39 39 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.195) 1. Pre-clinical Research • • 按一下以編輯母片標題樣式 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 40 40 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.195) 2. Clinical Research 按一下以編輯母片標題樣式 (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 41 41 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.195) 2. Clinical Research 按一下以編輯母片標題樣式 (a) Phase 1 To investigate the metabolism, the structure-reactivity relationships, the mechanism of action and the side effects of the drug in humans 42 42 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.195) 2. Clinical Research 按一下以編輯母片標題樣式 (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 43 43 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.195) 2. Clinical Research 按一下以編輯母片標題樣式 (a) Phase 2 • These studies are conducted on a larger scale than the phase 1 studies several hundreds of patients are involved 44 44 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) 2. Clinical Research 按一下以編輯母片標題樣式 (a) Phase 3 • Phase 3 clinical research aims to provide more information about the effectiveness and the safety of the drug 45 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 按一下以編輯母片標題樣式 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 • 按一下以編輯母片標題樣式 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) 47 47 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.195) Formulation Development • 按一下以編輯母片標題樣式 Researchers have to find out which formulation of the drug brings the greatest effect is the most suitable to the patients 48 48 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing • 按一下以編輯母片標題樣式 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 49 49 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing 按一下以編輯母片標題樣式 • 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 50 50 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing • 按一下以編輯母片標題樣式 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 51 51 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing 按一下以編輯母片標題樣式 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 52 52 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing • • 按一下以編輯母片標題樣式 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 53 53 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing • 按一下以編輯母片標題樣式 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 54 54 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.196) Approval for Marketing • • 按一下以編輯母片標題樣式 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 55 55 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 7B 36.4 Over-the-Counter Drugs and Prescription Drugs 56 56 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 按一下以編輯母片標題樣式 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 57 57 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 按一下以編輯母片標題樣式 Name Aspirin (e.g. Cortal) • As analgesics and antipyretics Acetaminophen (e.g. Panadol) • As analgesics and antipyretics 58 58 New Way Chemistry for Hong Kong A-Level Book 3A OH Aspirin 1 O 按一下以編輯母片標題樣式 Analgesics and antipyretics 2 O O CH3 2-(acetyloxy)benzoic acid 59 59 New Way Chemistry for Hong Kong A-Level Book 3A 1 HO NH CH3 按一下以編輯母片標題樣式 O Acetaminophen 4 Analgesics and antipyretics N-(4-hydroxyphenyl)acetamide 60 60 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 按一下以編輯母片標題樣式 Name Vitamin C 61 61 • 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 按一下以編輯母片標題樣式 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 62 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 按一下以編輯母片標題樣式 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 63 63 New Way Chemistry for Hong Kong A-Level Book 3A Albuterol CH3 Treating asthma, emphysema 按一下以編輯母片標題樣式 NH H3C CH3 and chronic bronchitis 2 HO 1 4 2 OH 1 OH 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol 64 64 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 按一下以編輯母片標題樣式 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) 65 65 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 按一下以編輯母片標題樣式 • 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 - 66 66 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 Halogenated pheniramines are up to 20-fold more potent than pheniramine 67 67 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 36.5 Narcotics and their Adverse Effects 68 68 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) 按一下以編輯母片標題樣式 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) 按一下以編輯母片標題樣式 Unlike aspirin, narcotic analgesics produce euphoria, a feeling of great happiness or well-being are addictive 70 70 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) • 按一下以編輯母片標題樣式 Heroin and morphine are obtained by evaporating the sap of the opium poppy generally called opiates 71 71 New Way Chemistry for Hong Kong A-Level Book 3A 36.5 Narcotics and their Adverse (SB p.199) Morphine and Heroin • 72 72 按一下以編輯母片標題樣式 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 73 73 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 74 74 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 hydrochloride 75 75 New Way Chemistry for Hong Kong A-Level Book 3A 36.5 Narcotics and their Adverse (SB p.199) Draw the structures of morphine hydrochloride 按一下以編輯母片標題樣式 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 76 76 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 heroin 77 77 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 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 78 78 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: 79 79 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 80 80 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 81 81 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 82 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 按一下以編輯母片標題樣式 Commonly observed problems: 83 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: 84 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) 按一下以編輯母片標題樣式 New government posters against drug abuse 85 85 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 http://www.nd.gov.hk/en/antidrug_resources.htm 86 86 New Way Chemistry for Hong Kong A-Level Book 3A 按一下以編輯母片標題樣式 36.6 Stimulants and their Adverse Effects 87 87 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.200) Stimulants(興奮劑) 88 88 按一下以編輯母片標題樣式 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 : - 按一下以編輯母片標題樣式 Amphetamine (Yaba, Ice) Cocaine (crack, snow) Ecstasy(搖頭丸/忘我/狂喜/E仔) 89 89 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.200) Ketamine(氯胺酮) • 按一下以編輯母片標題樣式 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 90 90 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.200) Ketamine(氯胺酮) • 按一下以編輯母片標題樣式 First used on American soldiers during the Vietnam War, but it is often avoided now it can cause unpleasant out-of-body experiences • 91 91 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) 按一下以編輯母片標題樣式 Keto group 2o amine * * chiral centre 92 92 New Way Chemistry for Hong Kong A-Level Book 3A Ketamine(氯胺酮) 按一下以編輯母片標題樣式 C H ClNO 13 2 Cl 2-(2-chlorophenyl) 16 1 NH 2 1 CH3 2-(methylamino) O 2-(2-chlorophenyl) -2-(methylamino) cyclohexanone 93 93 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 • 按一下以編輯母片標題樣式 At low doses causes an increase in heart rate gives a mild, dreamy feeling and drowsiness 94 94 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 • 按一下以編輯母片標題樣式 At higher doses produce a hallucinogenic effect(幻覺) may cause the users to feel very far away from their body 95 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 • 按一下以編輯母片標題樣式 Frequent intake of ketamine can cause depression nausea impaired long-term memory and cognitive difficulties impaired motor function, respiratory and heart problems 96 96 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 • 按一下以編輯母片標題樣式 Frequent intake of ketamine can cause a tremendous physiological /psychological dependence addiction 97 97 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) Phenylethanamine and 按一下以編輯母片標題樣式 Substituted Phenylethanamines • 98 98 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 按一下以編輯母片標題樣式 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 99 99 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) Phenylethanamine and 按一下以編輯母片標題樣式 Substituted Phenylethanamines • Phenylethanamine may have psychoactive effects in sufficient quantities, but quickly metabolized in our body 100 100 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) Phenylethanamine and 按一下以編輯母片標題樣式 Substituted Phenylethanamines • Substituted Phenylethanamine a broad and diverse class of compounds include hormones, stimulants, hallucinogens(迷幻劑) and antidepressants(抗鎮抑劑) 101 101 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) Phenylethanamine and 按一下以編輯母片標題樣式 Substituted Phenylethanamines Amphetamine a homologue of phenylethanamine carrying an methyl group * 102 102 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) Phenylethanamine and 按一下以編輯母片標題樣式 Substituted Phenylethanamines Amphetamine 103 103 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 按一下以編輯母片標題樣式 Substituted Phenylethanamines Amphetamine 104 104 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 • 按一下以編輯母片標題樣式 The side effects: insomnia(失眠) Irritability(煩躁) loss of appetite hallucination(幻覺) heart and kidney failure tolerance 105 105 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 按一下以編輯母片標題樣式 Chronic users of amphetamines: 106 106 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 按一下以編輯母片標題樣式 Chronic users of amphetamines: more prone to illness develop mental disturbance known as amphetamine psychosis(精神病) 107 107 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.203) 按一下以編輯母片標題樣式 The END 108 108 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.191) 按一下以編輯母片標題樣式 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 109 109 Back New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.192) 按一下以編輯母片標題樣式 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 110 110 2-Hydroxybenzoic acid New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.192) 按一下以編輯母片標題樣式 (a) What extra atoms have to be added to phenol to give 2-hydroxybenzoic acid? (a) 1 carbon atom and 2 oxygen atoms 111 111 New Way Chemistry for Hong Kong A-Level Book 3A Answer 36.2 Development of Aspirin and cis-Platin (SB p.192) Back 按一下以編輯母片標題樣式 (b) Suggest reagents and conditions necessary to bring about the change from phenol to 2-hydroxybenzoic acid. (b) 112 112 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) 按一下以編輯母片標題樣式 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) 113 113 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) 按一下以編輯母片標題樣式 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 114 114 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.192) 按一下以編輯母片標題樣式 (b) 115 115 New Way Chemistry for Hong Kong A-Level Book 3A 36.2 Development of Aspirin and cis-Platin (SB p.192) Back 按一下以編輯母片標題樣式 (b) 116 116 New Way Chemistry for Hong Kong A-Level Book 3A 36.3 Key Stages of Drug Development (SB p.197) 按一下以編輯母片標題樣式 (a) What is the lead compound of aspirin? (a) 117 117 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) 按一下以編輯母片標題樣式 (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. Back 118 118 New Way Chemistry for Hong Kong A-Level Book 3A 36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.199) 按一下以編輯母片標題樣式 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. 119 119 New Way Chemistry for Hong Kong A-Level Book 3A 36.4 Over-the-Counter Drugs and Prescription Drugs (SB p.199) 按一下以編輯母片標題樣式 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. Back 120 120 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.201) 按一下以編輯母片標題樣式 Based on the structural formula of ketamine shown above, answer the following questions: (a) Give the molecular formula of ketamine. Answer (a) C13H16ClNO 121 121 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.201) 按一下以編輯母片標題樣式 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 122 122 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.201) 按一下以編輯母片標題樣式 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) Back 123 123 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) 按一下以編輯母片標題樣式 (a) Is amphetamine a primary, secondary or tertiary amine? (a) A primary amine 124 124 New Way Chemistry for Hong Kong A-Level Book 3A 36.6 Stimulants and their Adverse Effects (SB p.202) 按一下以編輯母片標題樣式 (b) Mark the chiral centre of the molecule of amphetamine in its structural formula. (b) (*chiral centre) Amphetamine 125 125 Back New Way Chemistry for Hong Kong A-Level Book 3A