Nicotine

1. Morphine Caffeine Plant: Opium poppy (Papaver somniferum) Plant: Tea (Camellia sinensis) and others Use: analgesic Use: central nervous system stimulant Credit: nchenga Credit: ykanazawa Molecular formula: C17H19NO3 Molecular formula: C8H10N4O2 Molecular weight (g): 285.3 Molecular weight (g): 194.2 Toxicity (LD50mouse mg/kg): 135 Toxicity (LD50mouse mg/kg): 62 Cost per 100mg (£): 14.77 Cost per 100mg (£): 1.25 Did you know? Laudanum, a potent painkilling medicine made from opium poppies, is documented as far back as 1522 Did you know? Plants like tea and coffee produce caffeine as an insecticide to poison bugs which try to feed on the leaves. Cocaine Nicotine Plant: Coca plant (Erythroxylum coca) Plant: Tobacco (Nicotiana tabacum) Use: local anaesthetic, stimulant Use: stimulant, insecticide Credit: moche Credit: iheartpandas Molecular formula: C17H21NO4 Molecular formula: C8H14N2 Molecular weight (g): 303.4 Molecular weight (g): 162.2 Toxicity (LD50mouse mg/kg): 16 Toxicity (LD50mouse mg/kg): 0.3 Cost per 100mg (£): 4.39 Cost per 100mg (£): 0.73 Did you know? The original 1886 recipe for Coca-Cola included “a pinch of coca leaves” meaning, until 1906, it contained some cocaine! Did you know? Nicotine is more toxic than cocaine or heroin and smoking 40 cigarettes could be deadly (not to mention silly!) for a non-smoker Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012)

2. Codeine Taxol Plant: Opium poppy (Papaver somniferum) Plant: Pacific yew tree (Taxus brevifolia) Use: analgaesic Use: chemotherapy (breast cancer) Credit:: pellaea Credit: ykanazawa Molecular formula: C18H21NO3 Molecular formula: C47H51NO14 Molecular weight (g): 299.4 Molecular weight (g): 853.9 Toxicity (LD50mouse mg/kg): 54 Toxicity (LD50mouse mg/kg): 12 Cost per 100mg (£): 0.53 Cost per 100mg (£): 75.03 Did you know? Codeine is the world’s most widely used opiate drug. It is made by methylating the more abundant drug, morphine. Did you know? Taxol is also made by a fungus which lives in the tree bark. It is produced commercially in mixed plant/fungal cell cultures. Quinine Digoxin Plant: Cinchona tree (Cinchona ledgeriana) Plant: Foxglove (Digitalis purpurea) Use: anti-malaria Use: treating heart arrhythmia Credit:: freefotouk Credit:: USGS Molecular formula: C20H24N2O2 Molecular formula: C41H64O14 Molecular weight (g): 324.4 Molecular weight (g): 780.9 Toxicity (LD50mouse mg/kg): 68 Toxicity (LD50mouse mg/kg): 7.7 Cost per 100mg (£): 1.66 Cost per 100mg (£): 28.91 Did you know? Quinine was the first effective treatment for malaria. Tonic water glows under UV light as it contains quinine – go on, try it! Did you know? In 2006 an American nurse was convicted of killing 40 patients with overdoses of digoxin and given 18 life sentences This resource was created by Dr Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012)

3. Aspirin Ephedrine Plant: Willow tree (Salix alba) Plant: ma huang (Ephedra sinica) Use: analgaesic, blood thinner Use: stimulant, decongestant Credit: alexlomas Credit: jimvanmeggelen Molecular formula: C7H6O3 Molecular formula: C10H15NO Molecular weight (g): 138.1 Molecular weight (g): 165.2 Toxicity (LD50mouse mg/kg): 184 Toxicity (LD50mouse mg/kg): 74 Cost per 100mg (£): 0.03 Cost per 100mg (£): 0.03 Did you know? Hippocrates, who lived around 400BC, recorded using a powder made from willow bark to treat pain and fever. Did you know? Ephedrine is closely related to drugs like speed. Ma huang has been used in traditional Chinese medicine for 5000 years. Quinidine Strychnine Plant: Cinchona tree (Cinchona ledgeriana) Plant: Strychnine tree (Strychnos nux-vomica) Use: treating heart arrhythmia Use: rat poison Credit: lalithamba Credit:: USGS Molecular formula: C20H24N2O2 Molecular formula: C21H22N2O2 Molecular weight (g): 324.4 Molecular weight (g): 334.4 Toxicity (LD50mouse mg/kg): 53.6 Toxicity (LD50mouse mg/kg): 0.41 Cost per 100mg (£): 0.10 Cost per 100mg (£): 0.65 Did you know? Quinidine is an isomer of quinine – they have the same chemical formula, but different structures and properties Did you know? Strychnine is the poison of choice in numerous books and films, including the movie ‘Psycho’ and Agatha Christie novels. Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012)

4. Vinblastine Tetrahydrocannabinol Plant:Madagascar periwinkle (Catharanthus roseus) Plant: Cannabis (Cannabis sativa) Use: chemotherapy (leukaemia) Use: analgesic, anti-emetic Credit: M. MartinVicente Credit: Kew Gardens Molecular formula: C46H58N4O9 Molecular formula: C21H30O2 Molecular weight (g): 810.9 Molecular weight (g): 314.5 Toxicity (LD50mouse mg/kg): 15 Toxicity (LD50mouse mg/kg): 42 Cost per 100mg (£): 119.41 Cost per 100mg (£): 123.65 Did you know? The Madagascar periwinkle was used as a folk remedy for centuries before the active chemicals were isolated in the 1950s Did you know? Synthetic tetrahydrocannabinol, known as dronabinol, is available on prescription in the USA for treating anorexia and nausea. Vincristine Theobromine Plant:Madagascar periwinkle (Catharanthus roseus) Plant: Cocoa (Theobroma cacao) Use: chemotherapy (leukaemia) Use: diuretic, vasodilator Credit: Steve Linder Credit: Kew Gardens Molecular formula: C46H56N4O10 Molecular formula: C7H8N4O2 Molecular weight (g): 824.9 Molecular weight (g): 180.2 Toxicity (LD50mouse mg/kg): 3 Toxicity (LD50mouse mg/kg): 837 Cost per 100mg (£): 579.73 Cost per 100mg (£): 0.07 Did you know? Extracting this drug from the plant is a slow process with low yields, but the molecule is too complicated to make synthetically. Did you know? Dogs metabolise theobromine more slowly than humans and can be poisoned with just one bar of chocolate. Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012)

5. Topotecan Reserpine Plant: Happy tree (Camptotheca acuminata) Plant: Snake root (Rauwolfia serpentina) Use: chemotherapy (ovarian & lung cancer) Use: high blood pressure,anti-psychotic Credit: kadavoor Credit: scott.zona Molecular formula: C23H23N3O5 Molecular formula: C33H40N2O9 Molecular weight (g): 421.4 Molecular weight (g): 608.7 Toxicity (LD50mouse mg/kg): 7.5 Toxicity (LD50mouse mg/kg): 21 Cost per 100mg (£): 23,042.66 Cost per 100mg (£): 390.34 Did you know? Topotecan inhibits the enzyme DNA topoisomerase and stops cancerous cells replicating. Did you know? In India, home of the Snake Root plant, this drug has been has been popular for centuries – even Mahatma Gandhi used it! Irinotecan Capsaicin Plant: Happy tree(Camptotheca acuminata) Plant: Chilli peppers (Capsicum sp.) Use: chemotherapy (colorectal cancer) Use: treating nerve pain and arthritis Credit: Ben Geach Credit: scott.zona Molecular formula: C33H38N4O6 Molecular formula: C18H27NO3 Molecular weight (g): 586.7 Molecular weight (g): 305.4 Toxicity (LD50mouse mg/kg): 132 Toxicity (LD50mouse mg/kg): 0.4 Cost per 100mg (£): 1336.00 Cost per 100mg (£): 62.40 Did you know? Irinotecan and topotecan are derivatives of naturally occurring camptothecin which is used in Chinese herbal medicine. Did you know? Capsaicin creates a burning sensation on the skin which blocks pain signals – you might have experienced it eating chillies! This resource was created by Dr Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012)

6. Theophylline Diosgenin Plant: Tea (Camellia sinensis) Plant: Yams (Dioscorea sp.) Use: muscle relaxant and bronchodilator Use: contraceptive Credit: nchenga Credit: IITA Molecular formula: C7H8N4O2 Molecular formula: C27H42O3 Molecular weight (g): 180.2 Molecular weight (g): 414.6 Toxicity (LD50mouse mg/kg): 136 Toxicity (LD50mouse mg/kg): >8000 Cost per 100mg (£): 3.17 Cost per 100mg (£): 0.74 Did you know? If you have asthma a cup of tea might help! Theophylline was developed as an asthma treatment drug in the 1950s. Did you know? Diosgenin is a precursor of the hormone progesterone and research on this plant in the 1940s led to the first contraceptive pill Colchicine Tubocurarine Plant: Autumn crocus (Colchicum autumnale) Plant: Curare (Chondrodendron tomentosum) Use: treating gout Use: muscle relaxant, nicotine withdrawal Credit: NTBG Credit: Dietmut Molecular formula: C22H25NO6 Molecular formula: C37H41N2O6 Molecular weight (g): 399.4 Molecular weight (g): 609.7 Toxicity (LD50mouse mg/kg): 1.7 Toxicity (LD50mouse mg/kg): 0.13 Cost per 100mg (£): 19.68 Cost per 100mg (£): 7.92 Did you know? Once common, this drug is very toxic and has nasty side effects (like diarrhoea) so is now only used for short term, acute cases Did you know? South American natives used this plant extract to poison their arrow heads and blow darts when hunting as it paralyses victims. Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012

7. Heroin Plant: Opium poppy (Papaver somniferum) Plant: Use: analgaesic Use: Credit: ykanazawa Molecular formula: C21H23NO5 Molecular formula: Molecular weight (g): 369.4 Molecular weight (g): Toxicity (LD50mouse mg/kg): 21.8 Toxicity (LD50mouse mg/kg): Cost per 100mg (£): 692.00 Cost per 100mg (£): Did you know? Heroin is actually the ‘trade name’ for diamorphine and from 1898 to 1910 could be bought freely as a cough suppressant. Did you know? This resource was created by Dr Science & Plants for Schools (www.saps.org.uk) This resource was created by Dr Sarah McLusky, lecturer in biochemistry at Newcastle College (details correct as of 2012