Saturday, June 25, 2011

IB Chemistry, Stereoisomerism, Optical isomers, Stimulants, Methamphetamine, Amphetamine in Organic Chemistry

Stereoisomers, Enantiomers, Stimulants, Methamphetamine in Medicine Drugs Option D
Stereoisomerism are isomers with same Molecular Formula + Structural Formula but different in spatial arrangement ( different 3 Dimensional shapes )

Optical Isomers (ORGANIC)
  • Chiral or Asymmetrical Carbon 
  • 4 different gps attached to carbon central
  • Non superimposable
  • Mirror image ( right, left handed )
  • Enantiomers - stereoisomers are mirror image to each other
  • Identical chemical/physical properties 
  • Enantiomers rotate plane of polarised light to diff directions
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Optical Isomers.(Stereoisomers)
1st - Thalidomide, 2nd - Methamphetamine, 3rd - Ephedrine
    1st Optical isomers - (Thalidomide) 
    Thalidomide drug 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 racemic mix (R)/(S) which is cheaper.
    • (R) is effective but (S) has side effect.
    • Enzyme recognises only one enantiomer due to active site


    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)
    ....................................................................................................................................................
    2nd Optical Isomer - Methamphetamine
    Methamphetamine known as (Meth, Ice, Speed) is a potent stimulant of central nervous system  
    Meth Structure and its Medical uses
    • Add methy gp to Amphetamine 
    • One chiral center, with 2 isomers R/L or S/D. 
    • (S) isomer (Stimulant) to treat ADHD, narcolepsy, fatigue, obesity
    • (R) isomer  is used in nasal congestion
    source:http://www.chm.bris.ac.uk/motm/methamphetamine/methv.htm



    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 (designer drug)
    source:http://www.chm.bris.ac.uk/motm/methamphetamine/methv.htm

    How R (legal) and S (illegal) isomer works
    Vicks VapoRub® Inhaler -50 mgs of the (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



    Winter Olympics
    • 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
    ......................................................................................................................................................
    3rd Optical Isomer - Ephedrine

    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




     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( thermogenesis ) and 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 Optical 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





    Medical uses of (1R,2S) Ephedrine isomer
    • Weight loss and diet
    • Ephedrine increases metabolic rate and stimulate lipolysis/glycogenolysis




    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
    Basic Household Ingredients 
    • Ephedrine source from pharmacy
    • Solvent
    • HCI
    • Lithium batteries 
    • Ammonia
    • Iodine
    • Phosphorus from matchbox
    • Chem 101 knowledge


    Meth abuse if there is no control on certain drugs prescription
    .....................................................................................................................................................
    Tutorial on Stereoisomers, Stimulants and Methamphetamine
    Faces of Meth users and our deepest sympathies to lost souls. 

    Faces of Meth - The best free videos are right here
    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
    Thanks to all pictures and video contributors for the above post

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