Tuesday, 29 November 2011

The Chemistry Behind Psuedoephedrine

<!Ø  Type: Small Molecule
Ø  Origin: Comes from the plant Ma Huang, or “Ephedra” which is processed into Ephedrine.
<!Ø  Ephedrine is then broken down further to extract “Pseudoephedrine” which is used in cough and cold, allergy, and other decongestant medicines.
Ø  Commonly, medicine using pseudoephedrine is referred to as “Sudafed”
Ø  Main Use: Treatment of several disorders such as asthma, rhinitis and urinary incontinence. Also used for its stimulatory effects on the central nervous system for narcolepsy and depression
Ø  Structure:






Ø Chemical Formula:  
10H15NO
Ø  IUPAC Name:

 (1S, 2S)-2-(methylamino)1-phenylpropan-1-ol
Ø  Kingdom: Organic

Ø  Classes: Phenethylamines, Amphetamines

Monday, 28 November 2011

Pseudoephedrine and its Effects on the Body

Ø  Pseudoephedrine was originally used to relieve nasal congestion caused by colds, allergies and hay fever.
Ø  It temporarily relieves sinus congestion and pressure by reducing the inflammation of the nasal passages, although it does NOT treat the cause of the symptoms or speed recovery
Ø  Some medications containing pseudoephedrine include:
·         Afrinol
·         Cenafed
·         Pseudocot
·         Ridafed
·         Efidac
·         Children’s Sudafed Nasal Decongestant
Ø  In more recent years, it was discovered that Pseudoephedrine contains the molecule known as an amphetamine, which stimulates the body. This drug could be used as a performance enhancer for many highly competitive athletes
Ø  When taken, pseudoephedrine increases blood pressure and heart rate
Ø  It also increases energy expenditure through increased lypolysis (increase of energy loss through fat burning). This assists in increased weight loss
Ø  Use of drug increases basal metabolic rate through thyroxine (iodine containing hormone and amino acid)
Ø  Use also suppresses appetite which decreases food intake
Ø  Side effects include:
·        Restlessness
·         Nausea
·         Vomiting
·         Weakness
·         Headache
·         Racing Heart
·         Shortness of Breath
·         Dizziness
** Side effects can be seriously worsened with the intake of caffeine or alcohol**
Ø  While short term the effects can be positive (such as enhanced athletic performance and more alertness and awareness), the drug contains an amphetamine. This can be addictive to the human body, if it's short term positive effects on performance aren’t already addicting enough.
Ø  Where the drug becomes dangerous is when the dose exceeds the daily recommendation, when it is taken with other drugs especially those such as alcohol and caffeine, and when the drug is taken in extremely high temperatures, especially during sports.

Drugs in the Sports Industry

Ø  Generally Speaking, in the past decade, performance enhancing supplements have grown to a $1.6 billion industry
Ø  In 1994 under a Federal “Dietary Supplement Health and Education Act” that a supplement was considered to be anything and everything from electrolytes in Gatorade to stimulants and hormones that can have serious, dangerous side effects.
Ø  The act states that supplements do NOT need to undergo the thorough and rigorous efficacy and safeties testing like “drugs” do.
Ø  This act would unknowingly allow some unrestricted sale of compounds that are not normally found in the average human diet, so long as they are considered to be from “natural sources”.
For example:
·         Thyroid-stimulating hormones can be sold as a fat burning supplement
·         Body builders can swallow testosterone in hopes of building lean muscle





Pseudoephedrine in the Sports Industry

Ø  Ephedrine is a derivative of the Ma Huang shrub, and when further synthesized, Ephedrine is known as Pseudoephedrine.
Ø  “Sudafed” is the more or less casual name for Pseudoephedrine that is seen on many cold and allergy medication bottles.
Ø  Pseudoephedrine can be accessed in tablets, capsules or herbal form.
Ø  It is a less commonly seen drug in the sports world as it is more difficult to obtain in North America and hard to avoid passing tests with.
Ø  Testing for Pseudoephedrine is done by a urine sample that is processed to see if it's contents contain methamphetamines (as a key component of Pseudoephedrine is the stimulant, amphetamines)
Ø  If it was desired to take the testing further, the more accurate test would be Gas
Chromatograph/Mass Spectrometer (GC/MS) test.
Ø  Pseudoephedrine can sometimes be considered dangerous if exceeding the amount of dose that is recommended, as is any drug.
Ø  However, pseudoephedrine is considered the most dangerous when taken alongside other drugs especially those including caffeine and alcohol.
Ø  The use of Pseudoephedrine is most commonly seen in sports such as Track and Field, Football and Body Building which all rank less than 5% testing positive per year.
Ø  While it is possible for Pseudoephedrine to cause death, it is rare when taken properly.
Ø  Two recorded cases of death involving Pseudoephedrine are:
·         Minnesota Vikings offensive tackled Korey Stringer during a Summer Training camp who died of heat stroke. Autopsy results revealed that high heat and high blood pressure caused by pseudoephedrine were the leading cause of death.


·         Baltimore Orioles pitcher Steve Bechler also passed due to heat stroke during the summer league when high heat and high blood pressure overtook the strength of his respiratory system. Autopsy results stated that he had induced a high overdose of pseudoephedrine into his system prior to death.



Laws Regarding Pseudoephedrine

Ø  - Pseudoephedrine is the ingredient of many proprietary medicines which are available over the counter
Ø  - The Body converts this drug into “Cathine” which can be harmful to the body in high doses
Ø  - Until the end of 2003, PSE (pseudoephedrine) was a banned stimulant substance in sport (in the case that concentration was greater than 25 micrograms per ml)
Ø  - The World Anti Doping Agency (WADA) removed PSE from the prohibited list
Ø  - Prior to 2004, Cathine was a banned substance (and is to this day)
Ø -  The results of a doping control concerning PSE was conducted in the Department of Anti-Doping research institute of sport between the years of 2001-2003 and 2004- 2007. Results were compared:
·         In samples that were taken, PSE and Cathine were estimated before evaluation
·         The results show that athletes were using PSE frequently and in high doses between 2004-2007 (when permitted by WADA)
·         It was possible that athletes can obtain a positive result of doping with Cathine after sufficient use of PSE.

Case Study


Subject: Silken Laumann (Female)
Sport: Canadian Olympic Rower
Studied From: 1992-1996
Performance Enhancing Drug: Pseudoephedrine/ Ephedrine



Born November 14, 1964 in Mississauga Ontario, Silken Laumann and her sisters' Career started out on the track and field circuit. When the Laumann sisters switched over to the sport of Rowing, their career into the National Team was short and powerful. They succeeded with fast rates, adding promise to the national team in the coming Olympic years with their strong muscle performance and outstanding results. When Silken’s sister retired early to start a different life, Silken pushed on without her, practicing in the single and quadruple sculls.

Unfortunately for Silken Laumann, tragedy struck in May, 1992, 10 weeks before the 1992 Summer Olympic Games in Barcelona. Laumann was involved in a brutal rowing accident where she and another “sculler” collided with an impact that drove the splashboard right into her lower left leg. “The muscles on the outside of my right leg were peeled back and hanging down to the ankle … the doctors thought I would never row again.” Silken had said. She sustained an open tibia fracture with concurrent nerve damage and lost a sufficient amount of skin and soft tissue that permanently weakened her left leg. It was a brutal heartbreak for Laumann, who had made the immediate decision to not give up so quickly.

Remarkably enough, 27 days later, with 5 operations and countless hours of rehabilitation, Laumann sat back in her shell for the very first time and began her continued training for the Olympics that were now just around the corner.

                On August 2nd, 1992, Silken made the biggest comeback in Canadian Sports History, taking home a bronze medal for Canada that shed light into the hearts of other athletes struggling to achieve their dreams.

                An international star known all over the world, Canada was proud to be represented by Silken Laumann as she continued her training for up and coming international competitions. Such as the World Championships, the Pan Am Games in 1995 and the 1996 Summer Olympics in Atlanta.

                Another downfall for Silken struck on Wednesday March 23, 1995 during her competition at the Pan Am Games. She yet again astonished the world when she won a gold medal in the single sculling and another gold medal in the quadruple sculling. Laumann was one of the greatest rowers until the world, that is, until she drug tested positive. Silken Laumann has tested positive for Ephedrine/ Pseudoephedrine right after her competition at the Pan American Games. For that, she and her team of 4 were stripped of their Gold Medals, a massive shock to all who witnessed.

                Olympic officials stated that never has a Female Canadian Rower tested positive for a banned substance. The likelihood is that the drug was inadvertently taken by the athlete who was suffering from a cold and in need of some medicine before her big competition. But all in all, Silken was not given back her Medals and was sent back home with her head hanging in shame.

                Although she was stripped of two of some of the greatest things that have ever happened to her, the determination never left her bones and she hit the water again with all necessary force. She made an immediate comeback the following year for the 1996 Atlanta games winning a Silver Medal for Canada, proving that she deserved to be there just as much as any other athlete.

                All in all, no matter what downfall or uprising Silken had to push through, the road to the top is never and has never been easy, and Silken Laumann charged the mountain with all force and determination. This is why despite her run in with Ephedrine and the law, she is considered one of the greatest and most well known retired rowers of all time. 

Sunday, 27 November 2011

Works Cited

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"Pseudoephedrine Information from Drugs.com." Drugs.com | Prescription Drug Information, Interactions & Side Effects. Cerner Multum Inc., 18 Apr. 2011. Web. 27 Nov. 2011. <http://www.drugs.com/pseudoephedrine.html>


"Pseudoephedrine | The Partnership at Drugfree.org." The Partnership at Drugfree.org | Support and Resources for Parents Dealing with Teen Drug and Alcohol Abuse. National Institute of Health, n.d. Web. 27 Nov. 2011. <http://www.drugfree.org/drug-guide/pseudoephedrine>.


"Pseudoephedrine: MedlinePlus Drug Information." National Library of Medicine - National Institutes of Health. Medline Plus, 8 July 2011. Web. 27 Nov. 2011. <http://www.nlm.nih.gov/medlineplus/druginfo/meds/a682619.html>


Quinn,  Elizabeth. "Sports Supplements - Ephedrine and Athletic Performance." Sports Medicine, Sports Performance, Sports Injury - Information About Sports Injuries and Workouts for Athletes. N.p., 15 Oct. 2007. Web. 27 Nov. 2011. <http://sportsmedicine.about.com/cs/nutrition/a/aa030901g.htm>


Wright, Karen. "Bigger, Faster, Stronger Powders, Hormones and Herbs may boost performance-riskily." Discover Feb. 2002: 1 (Database). Print.