Molecular structure of pseudoephedrine
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Pseudoephedrine is a sympathomimetic amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations either as single-ingredient preparations, or more commonly in combination with antihistamines and/or paracetamol/ibuprofen. more...

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This agent is often referred to by consumers as Sudafed, which is the trademark for a common brand of pseudoephedrine hydrochloride. Other brand names include Afrinol, Novafed, and Cenafed.

Unlike antihistamines, which modify the systemic histamine-mediated allergic response, pseudoephedrine only serves to relieve nasal congestion commonly associated with colds or allergies. The advantage of oral pseudoephedrine over topical nasal preparations, such as oxymetazoline, is that it does not cause rebound congestion (rhinitis medicamentosa). However, the disadvantage of oral pseudoephedrine is that it can cause high blood pressure.

Nomenclature

Pseudoephedrine is the International Nonproprietary Name (INN) of the (1S,2S)- diastereomer of ephedrine (which has 1R,2S- configuration). Equivalent names are (+)-pseudoephedrine and D-pseudoephedrine. (Reynolds, 1989)

(-)-Pseudoephedrine or L-pseudoephedrine then designates the enantiomer of pseudoephedrine.

Chemistry

Pseudoephedrine, a phenethylamine, is a structural isomer of the popular weightloss/energy supplement and asthma medication, ephedrine. Ephedrine is an alkaloid extracted from the Ephedra plant, which produces it naturally as a racemic mixture. That is, ephedrine molecules occur as two "mirror images," inasmuch as a pair of hands do (See the article on entantiomers). The pharmacologic properties of each "reflection" often share similarities and differences. The (-) or levorotatory isomer is a very potent sympathomimetic amine and anorectic, thus responsible for the amphetamine-like stimulation that is characteristic of Ephedra products. The (+) or dextrorotatoryisomer, aka pseudoephedrine, is far less potent as a stimulant. However, it retains much of ephedrine's ability to open airways and nasal passages.

Mode of action

Pseudoephedrine is a sympathomimetic amine - that is, its principal mechanism of action relies on its indirect action on the adrenergic receptor system. Whilst it may have weak agonist activity at α- and β-adrenergic receptors, the principal mechanism is to displace noradrenaline from storage vesicles in presynaptic neurons. The displaced noradrenaline is released into the neuronal synapse where it is free to activate the aforementioned postsynaptic adrenergic receptors.

The vasoconstriction that pseudoephedrine produces is believed to be principally an α-adrenergic receptor response. Whilst all sympathomimetic amines, to some extent, have decongestant action; pseudoephedrine shows greater selectivity for the nasal mucosa and a lower affinity for central nervous system (CNS) adrenergic-receptors than other sympathomimetic amines. (+)-(1S,2S)-pseudoephedrine shows far lower CNS activity than other Ephedra alkaloids, ephedrine, and (-)-(1R,2R)-pseudoephedrine.

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Banned substances in common medications
From Swimming World and Junior Swimmer, 10/1/99

Sixteen-year-old Rick DeMont (center) won the 400 meter freestyle at the Munich Olympics in 1972, but he was stripped of his gold medal five days later by the IOC because he had taken a banned medication (ephedrine) for an asthma condition.

In 1972, U.S. swimmer Rick DeMont won a gold medal at the Munich Olympics. The International Olympic Committee stripped him of that medal, however, when he failed the post-race drug test. Rick committed no crime. He was simply taking an asthma medication prescribed for him by his family doctor and approved by the USOC's doctor.

Unfortunately, neither Rick nor his doctors realized that the medication contained a banned substance.

Since 1972, dozens of other athletes around the world have suffered the same fate. The moral of these sad stories is don't trust your family doctor to know whether the medication he or she prescribes contains substances that are on FINA's prohibited list. Under FINA rules, an innocent mistake is no defense. If a prohibited substance is found in your urine, a doping offense has been committed, your results at that competition will be disqualified, and you may well be suspended for a period from future competition.

If you are competing at a level where you may be drug-tested, call the U.S. Olympic Committee Drug Hotline at 1-800-233-0393 to confirm for yourself that any medicine or supplement you are taking is OK.

Ironically, most drugs that are banned in sport have legitimate medical uses.

They are banned because they can be abused to build muscles and endurance (steroids), can mask the presence of other drugs or are stimulants.

The following is a list of some common types of medications and products which contain banned substances. This list is meant to be illustrative, not exhaustive:

Cold and Allergy Relief Medicines

Many cold and allergy relief medications contain the prohibited stimulants ephedrine or pseudoephedrine. These ingredients can be found in some common brand names of allergy, cold or flu medications, such as Actifed, Alka Seltzer, Bayer, Benadryl, Clorafed, Chlor-Trimeton, Comtrex, Dimetapp, Dorcal, Dristine, Drixoral, Efidac, Excedrin, Mytussin, Naldecon, Nyquil, Pediacare, Primatene, Rescon, Robitussin, Sudafed, Theraflu, Triaminic, Tritann, Tussafed, TussOrade, Tylenol and Vicks.

All of these medications containing stimulants are banned in-competition, but may be used out-of-competition. Obviously, use of these medications must be discontinued well in advance of any tested meet.

Supplements

The shelves of your local health food store are full of products that can cause you to fail a drug test. In particular, watch out for ephedrine, pseudoephedrine and ma huang (Chinese ephedrine), which are contained in many energy products.

Also watch out for androstenedione, norandrostenediol and norandrostenedione, which are prohibited steroids found in some "power" products.

Diet Products

Watch out for diet products to make sure that they don't contain a banned stimulant such as dexedrine.

Asthma/Bronchial Medications

Salbutamol, salmeterol and trebutaline are permitted by inhaler to treat asthma as well as exercised-induced asthma.

However, a declaration verifying medical necessity should be provided to the U.S. Olympic Committee in advance of competition. The use of prednisone is not permitted, and none of these substances may be taken orally or by injection.

ADHD Medication

The active ingredients in Ritalin (methylphenidate) and Cylert (pemoline), used to treat Attention Deficit Hyperactivity Disorder (ADHD), are stimulants which are prohibited incompetition, but not out-of-competition. Most athletes who are being treated for ADHD simply discontinue use in advance of competition.

Diabetes

Recently, insulin has been added to the FINA prohibited substances list. It is permitted only when pre-approved by the FINA Doping Control Review Board to treat insulin-dependent diabetes.

FINA has recently adopted a new rule which permits athletes to request advance permission to use a prohibited substance. The request is submitted to the FINA Doping Control Review Board. Although this board is newly created and does not have a track record, I would expect that exemptions will only be given when the medical problem is serious, well-documented and when alternative methods of treatments are not available.

Over the years, I have talked with many physicians who are outraged that sport doping rules might stand in the way of their legitimate treatment of athlete patients. Unfortunately, many doctors are simply not aware that legitimate medications can result in a positive drug test if they appear in an athlete's urine. The bottom line is that as a swimmer, you are held personally responsible for everything that goes into your body. You cannot rely on your doctor to understand which medications are prohibited and which are not. It is your responsibility to call the hotline and protect yourself.

-By Rich Young, USA Swimming Legal Counsel

Olympic Trials Tickets

USA Swimming and the Indiana Sports Corporation announced that tickets for the 2000 Olympic Trials went on sale Sept. 15. The meet, to be held Aug. 9-16, 2000, will be held at the Indiana University Natatorium for the third straight quadrennium. Check the USA Swimming web site for all the ordering information.

Officials Online

The USA Swimming web site now has a full section devoted to officials. This section will provide news, handbooks, guidelines and forms that officials at any level can utilize to keep informed and improve their skills.

Currently online are the latest copy of the officials 'newsletter, the complete text of "The Handbook for Officiating," starter training information, rules interpretations, certification tests and officials directories.

Copyright Sports Publications, Inc. Oct 1999
Provided by ProQuest Information and Learning Company. All rights Reserved

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