Saturday, June 18, 2011

IB Chemistry on Analgesics, Morphine, Heroin, Aspirin and Paracetamol

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 contain Morphine (10%) and Codeine (0.5%)
  • Strong analgesic/pain killer

source:http://www.britannica.com/EBchecked/topic/430129/opium


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 are OH, Amine, Alkene and Aromatic ring
  • Modified morphine (semi synthetic) - Heroin, Codeine, Demerol, Methadone, Hydromorphone, Oxymorphone

Click HERE to view 3D structure




Active site of morphine and derivatives
Active Site
  • Amine (tertiary) gp attached
  • Aromatic ring
  • Quartenary Carbon center
  • Morphine, Codeine, Heroin - similar active site acts on analgesic receptors (Brain/CNS)









Morphine Modification/ Derivatives (semi synthetic)
Three Structural Similarities


1. 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
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
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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




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
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
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Mild Analgesic drugs, Aspirin, Paracetamol,
Aspirin, salicylate drug acts on enzyme producing prostagladins - mild analgesic, as an antipyretic to reduce fever and an anti-inflammatory.


Aspirin ( acetylsalicylic acid ) made from salicylic acid and acetic anhydride.






  • Active ingredient from Willow Bark ( Salicylic acid ),
  • Acidic due to OH group of phenol.
  • Adding acetyl gp changes it to Aspirin (Less acidic).


How Aspirin Works
  • Aspirin decrease production of prostaglandins by inhibiting (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
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Mild Analgesic Paracetamol, (Tylenol), (Acetaminophen)
Good side of Paracetamol
  • Inhibit prostaglandin synthesis
  • Mild Analgesic, Antipyretic,
  • Weak/Little Anti-inflammatory or Stomach bleeding
  • Benzene ring, one 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)
Video Tutorial on Strong/Mild Analgesics
IB Chemistry, analgesics, opiates, morphine, paracetamol and aspirin
 
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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

Click HERE for more info on eating bagel (poppy seeds)
Thanks to all pictures and video contributors for the above post

2 comments:

  1. Codeine is a narcotic opioid drug like oxycodone and hydrocodone. It is similar in properties to these generic drugs. Findrxonline in his blog points out that It is a derivative of the opium plant and inevitably possesses similar characteristics like any other derivative of the opium like heroin and morphine. It is used for the treatment of mild to moderate pain and is used as an analgesic. It is also used as a cough suppressant and treats cough effectively as it possesses antitussive properties. It is a prescription and can be availed only through a prescription drug. However one can buy cheap Codeine online without prescription easily.

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