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IB Chemistry, Stereoisomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs

IB Chemistry, Stereoisomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs



Stereoisomerism, optical isomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs Option D

Stereoisomerism, optical isomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs Option D



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    IB Chemistry, Stereoisomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs IB Chemistry, Stereoisomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs Presentation Transcript

    • Prepared by Lawrence Kok http://lawrencekok.blogspot.com
    • Stereoisomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs Option D Stereoisomerism are isomer with same Molecular Formula + Structural Formula but different in spatial arrangement ( different 3 Dimensional shapes ) Optical Isomers (Organic)
      • Chiral, Asymmetrical carbon
      • 4 different gps attached to carbon central
      • Non superimposable
      • Mirror image ( right, left handed )
      • Enantiomers – stereoisomers which are mirror image to each other
      • Identical chemical/physical properties 
      • 2 enantiomers rotate plane of polarised light to diff directions
    • Optical isomers (Thalidomide) 
      • Thalidomide exist as optical isomers 
      • Enantiomers (R) and (S)
      • (R) effective against  insomnia
      • and  morning sickness
      • (S) teratogenic, birth and limb defect
      In nature, our body synthesises enzyme which have active site for only one enantiomer
      • Drug company, synthesise drug with (R) and (S) (racemic mix)
      • (R) is effective but (S) has side effect
      • Enzyme recognises only one enantiomer due to active site
      Optical Isomers. (Stereoisomers) 1st - Thalidomide, 2nd - Methamphetamine, 3rd - Ephedrine
    • Mirror image of thalidomide caused limb deformation
      • (S) enantiomer causes limb defects and severe shortening of the arms /legs.
      • (R) enantiomer is effective drug
      • Body will convert (R) to (S) by racemisation process, producing a racemic mixture (R)/(S)
      source: http://dermatology.cdlib.org/93/reviews/thalidomide/hsu.htm source: http://chemwiki.ucdavis.edu/index.php?title=Special:Userlogin&returntomypage=y
      • 2nd Optical Isomer – Methamphetamine
      • Methamphetamine known as (Meth, Ice, Speed) is a potent stimulant of  central nervous system   
      • Derived from  amphetamine   class  of  psychoactive drugs
      • Affect brain neurotransmitters, including  dopamine ,  serotonin , and  norepinephrine .
      • Known as  sympathomimetic  drug (Stimulant)
      • Increase heart beat, blood pressure and use to treat asthma,  ADHD , obesity,  narcolepsy
      • Similar in structure with dopamine, increases dopamine level, feeling of pleasure and staying alert
      • High doses causes  euphoria  and addictive  
    • Optical isomers of Methamphetamine
      • Notation for optical isomer R/L or S/D
      • One  chiral  center, 2 optical  isomers  
      • (R) isomer, legal ( over-the-counter drug ) used in  inhalers  for nasal decongestion
      • (S) isomer, illegal, stimulant known as speed
      Meth Structure and its Medical uses
      • Add methy gp to Amphetamine 
      • One  chiral  center, with 2  isomers  
      • (S) isomer (Stimulant) to treat  ADHD , narcolepsy, fatigue, obesity
      • (R) isomer is used in nasal congestion
      source: htt p://www.chm.bris.ac.uk/motm/methamphetamine/methv.htm
    • How R (legal) and S (illegal) isomer works
      • (R) isomer -   sympathomimetic   vasoconstrictor  , available OTC as nasal  decongestants  including Vicks Vapor Inhaler.
      • Vicks VapoRub® Inhaler - 50 mgs of (R) isomer 
      • Works by constricting blood vessels in nasal, reduce flow, reduce inflammation and swelling
      • (S) isomer, illegal and causes intense euphoria and pleasure
      • Works by inducing dopamine rush into brain synapse (Structurally similar with dopamine)
      source: http://hhic.org/_cmx/cmx_article/articleView.asp?ArticleID=110
      • Salt Lake City Olympics 2002, Alain Baxter made British history, winning a medal (Bronze)
      • Unfortunately, tested positive for the banned stimulant methamphetamine 
      • Claimed to use Vicks nasal inhaler, (R) methamphetamine isomer
      • (S) methamphetamine isomer is a banned drug
      • Was cleared by IOC after investigation
      • Lose a medal because of Vicks nasal inhaler (R) isomer)!!!!
      • Click  HERE  for source and full story
      Winter Olympics
      • 3rd Optical Isomer - Ephedrine
      • Ephedrine  structurally similar to  amphetamine  and  methamphetamine
      • An  alkaloid  derived from plants  Ephedra  ( ephedrine and  pseudoephedrine  )
      • Medical use as  stimulant (alert/focus),  appetite suppressant  (weight control) nasal  decongestant  (cold/ flu)
      • Similar Structure - Amphetamine, Methamphetamine, Ephedrine
      • Ephedrine Structure
      • Epinephine has 2 chiral center - 4 stereoisomers
      • Meth has 1 chiral center - 2 stereoisomers
      • Alkaloids (nitrogen attached), sec amine gp
      • Difference bet Meth and Ephedrine - OH gp
      • Ephedrine acts as stimulants like Meth
      source : http://wwwchem.csustan.edu/chem4400/sjbr/carlson03.htm
    • 4 stereoisomers, Ephedrine/Pseudoephedrine
      • All 4 optical isomers have similar properties
      • (1R,2S) Ephedrine and (1S,2S) Pseudoephedrine are believed to be more potent than the rest
      • (1S,2S) Pseudoephedrine used as a  nasal decongestant  and cold/flu tablet
      • (1R,2S) Ephedrine used for weight control - stimulate metabolic, burning of fat
      • All acts as stimulant similar to Meth
      • They are called  diastereomers  (Not in IB)
      source : http://wwwchem.csustan.edu/chem4400/sjbr/carlson03.htm
    • Medical uses of (1S,2S) Pseudoephedrine isomer
      • Nurofen  contain (1S,2S) Pseudoephedrine
      • (1S,2S) Pseudoephedrine used as a  nasal decongestant  and cold/flu tablet
      • Works by constricting blood vessel in nasal, reduce blood flow, inflammation and swelling
      • source: http://www.nurofen.co.uk/products.php
      • Sudafed  contain (1S,2S) Pseudoephedrine for nasal decongestion
      • Works the same as above
      • source: http://www.sudafed.ca/en/sudafed_sinus.asp
      • Weight loss and diet
      • Ephedrine increases metabolic rate and stimulate lipolysis/glycogenolysis
      Medical uses of (1R,2S) Ephedrine isomer source: http://www.ephedrawarehouse.com/
      • Side effect of Ephedrine/Pseudoephedrine
      • Main health concern, acts as stimulant( blood vasoconstrictor) - Increase heart rate and blood pressure, may causing cardiovascular problems.
      • Many side effects, pls consult medical doctor
      • Easily available as flu/cold medication and subject to abuse (control item in some countries)
      • Benefits should be carefully weighed against side effects
      • Benefits and side effects. Click  HERE  to view
    • World Anti Doping Agency on Stimulants use in sports
      • List of Banned drugs (effect 1 Jan 2011)
      • Stimulants both optical isomers are banned 
      • Ephedrine, Pseudoephedrine banned but allow to certain amt.
      • Pseuso (<150ug/ml), Ephedrine (<10ug/ml)
      • R Meth banned but if you use S Meth (inhaler), or consume Pseudo/Ephedrine (cold/flu) medication before competition, you may lose a medal. Consult medical expert first!
      • Click  HERE  to view list banned items by World Anti Doping Agency
    • Why it is so easy to make Meth at home? Meth made from Pseudo/Ephedrine (easily available from pharmacy as Sudafed Pills)
      • Reduce OH on Ephedrine to H on Meth
      • Reducing agent 
      • Basic Chem 101 knowledge to make Meth
      • Will not elaborate on it as it is illegal
      • Ephedrine source from pharmacy
      • Solvent
      • HCI
      • Lithium batteries 
      • Ammonia
      • Iodine
      • Phosphorus from matchbox
      • Chem 101 knowledge
      Basic Household Ingredients Meth abuse if there is no control on certain drugs prescription
      • In short :
      • Never touch Meth as it will destroy your life, families body and soul.....
      • All you need to know about Meth, (video + animation+ victims).
      • Click  HERE  to view
      Video on Faces of Meth users and our deepest sympathies to lost souls. Click HERE to view 
    • 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