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IB Chemistry, analgesics, opiates, morphine, paracetamol and aspirin

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IB Chemistry, analgesics, opiates, morphine, paracetamol, aspirin for option D

IB Chemistry, analgesics, opiates, morphine, paracetamol, aspirin for option D

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  • 1. Prepared by Lawrence Kok http://lawrencekok.blogspot.com
  • 2. IB Chemistry, Analgesic, Medicine and Drug, Option D Strong Analgesic for Pain Relief
    • Opium poppy plant
    • Raw opium contain alkaloids -  morphine ,  thebaine , and  codeine
    • Raw opium -  Morphine (10%) and Codeine (0.5%)
    • Strong analgesic/pain killer 
    • source : http://www.britannica.com/EBchecked/topic/430129/opium
  • 3.
    • IB Keywords
    • Alkaloids - substance with nitrogen atoms. 
    • Narcotic -  psychoactive  compound with sleep-inducing and pain relief properties
    • Opiates -   alkaloids  semi synthetic drug derived from  opium poppy  plt, used for pain relief
    • Morphine - acts on opioid receptor on Brain/CNS, prevent transmission of pain
    • Needs prescription and are addictive
    • Morphine Structure 
    • Acts on receptor on  central nervous system .
    • Functional gps - OH, Amine, Alkene and Aromatic ring
    • Modified morphine (semi synthetic) - Heroin, Codeine, Demerol, Methadone, Hydromorphone, Oxymorphone 
    • Click  HERE  to view 3D structure 
  • 4.
    • Active Site
    • Amine (tertiary) gp attached
    • Aromatic ring 
    • Quartenary Carbon center
    • Morphine, Codeine, Heroin - similar active site acts on analgesic receptors (Brain/CNS)
    Active site of morphine and derivative Morphine Modification/ Derivatives (semi synthetic)
    • Three Structural Similarities
    • Benzene ring
    • 2. Amine gp
    • 3. Quartenary carbon(4 carbon neighbors)
    • picture from
    • http://www.emsb.qc.ca/laurenhill/science/morphine.html
    • http://www.ch.ic.ac.uk/rzepa/mim/drugs/html/morphine_text.htm
  • 5. Morphine modification to Semi synthetic drug (potent)
    • Morphine to Codeine
    • adding methyl gp ( less polar )
    • Morphine to Heroin
    • adding 2 acetyl gp/acetylation ( less polar)
    • OH replace by ethanoate gp
    • Less polar - Lipid soluble, More potent cause able to Absorb/Cross lipid based   blood-brain barrier   faster than morphine
  • 6. Potency of Morphine, Codeine, Heroin, Hydro/Oxymorphone Pharmacological Effects of opiates (Morphine)
    • Analgesic pain relief
    • binds to  μ- opioid  receptors, reducing   peristalsis  
    • in intestine producing constipating effect,
    • treat diarrhea ( antidiarrheal )
    • suppress coughing
    source : http://www.vocalscience.com/vocal_constipation.html
  • 7.
    • Psychological/Side effects 
    • Constipation, Nausea, Vomiting, Tolerance, physical dependence
    • Sterility, Withdrawal syndrome, Death if overdose
    • Prevent Depression /Morphine Overdose
    • Methadone, Naltrexone, Naloxone, Nalorphine
    • prevent morphine addiction, 
    • ( opiate   overdose ) or decreases craving
    • for opiates.
    • As antagonist, prevent morphine from binding to its receptor
    • picture: http://issues05.emcdda.europa.eu/en/elements/bupfig01-en.html
  • 8. Strongest Analgesic, Etorphine
    • Opioid alkaloids
    • 1000X more potent than morphine
    • Modification of side gp
    • Used for wild life immobilization
    Source: http://www.chm.bris.ac.uk/motm/etorphine/etorphineh.htm
  • 9.
    • Mild Analgesic drugs, Aspirin, Paracetamol, 
    • Aspirin,  salicylate   drug  
    • acts on enzyme producing prostaglandins
    •   mild analgesic, as an  antipyretic  to reduce fever 
    • an  anti-inflammatory .
    Aspirin ( acetylsalicylic acid ) made from salicylic acid and acetic anhydride. 
    • Active ingredient
    • Willow Bark ( Salicylic acid )
    • Acidic due to OH gp of phenol. 
    • Adding acetyl gp changes it to Aspirin (Less acidic ).
  • 10. How Aspirin Works
    • Aspirin decrease production of  prostaglandins  
    • by inhibit (COX) enzyme. 
    • Works by acetylating (add acetyl gp) to a  serine  residue on active site of the (COX) enzyme.
    • Aspirin inhibits COX enzyme, decrease prostaglandins (hormone) production
    •   pain relief, reduce inflammation or swelling
    • http://www.mydietaryfats.org/index.php/info/content/113 /
    Click  HERE  to view advantages and disadvantages of Aspirin
  • 11. Mild Analgesic Paracetamol, (Tylenol), (Acetaminophen) Good side of Paracetamol
    • Inhibit  prostaglandin  synthesis
    • Mild Analgesic, Antipyretic
    • Weak/Little Anti-inflammatory or Stomach bleeding
    • Benzene ring,  hydroxyl  and amide gp ( acetamide )
    • Popular without any prescription (OTC)
    • Bad side 
    • Acute overdose cause  liver damage
    • Blood disorder, kidney damage
    • Overdose fatal to child, cause death
    • (Click  HERE  for Calpol/Paracetamol dosage)
  • 12. Tragedy of mum who died after overdose 8:44am Tuesday 24th May 2011.Click  HERE  for info Eating bagel with poppy seeds (Codeine + Morphine), will you be tested positive for morphine Poppy Seed contain Morphine + Codeine Fail drug Test, bagels with poppy seed? Source: http://www.erowid.org/plants/poppy/poppy_testing.shtml Video, Tested positive eating bagels with Poppy seeds (on next slide) Click   HERE  for more info on eating bagel (poppy seeds) Thanks to all pictures and video contributors for the above post
  • 13. Acknowledgements Thanks to source of pictures and video used in this presentation Thanks to Creative Commons for excellent contribution on licenses http://creativecommons.org/licenses/ Prepared by Lawrence Kok Check out more video tutorials from my site and hope you enjoy this tutorial http://lawrencekok.blogspot.com