Prepared byLawrence Kokhttp://lawrencekok.blogspot.com

IB Chemistry, Analgesic, Medicine and Drug, Option DStrong 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

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 

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 Similarities1.Benzene ring

2. Amine gp

3. Quartenary carbon(4 carbon neighbors)

picture fromhttp://www.emsb.qc.ca/laurenhill/science/morphine.htmlhttp://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

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

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).

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

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)

Tragedy of mum who died after overdose8:44am 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 + CodeineFail 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

Acknowledgements

Thanks to source of pictures and video used in this presentation

Thanks to Creative Commons for excellent contribution on licenseshttp://creativecommons.org/licenses/

Prepared by Lawrence Kok

Check out more video tutorials from my site and hope you enjoy this tutorialhttp://lawrencekok.blogspot.com