Prepared byLawrence Kokhttp://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 insomniaand 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.htmsource: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:http://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 MethThey 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 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