Chemistry and sport
The use of performance-enhancing drugs in sport is commonly
referred to by the term "doping", particularly by those
organizations that regulate competitions. The use of performance
enhancing drugs is mostly done to improve athletic performance.
This is why many sports ban the use of performance enhancing
drugs. Another similar use of medical technology is called blood
doping, either by blood transfusion or use of the hormone
erythropoietin (EPO). The use of drugs to enhance performance is
considered unethical by most international sports organizations
and especially the International Olympic Committee, although
ethicists have argued that it is little different from the use of
new materials in the construction of suits and sporting
equipment, which similarly aid performance and can give
competitors an unfair advantage over others. The reasons for the
ban are mainly the alleged health threat of performance-enhancing
drugs, the equality of opportunity for athletes, and the
exemplary effect of "clean" ("doping-free") sports for the
The use of these or related drugs has been found in horse racing
and other equestrian sports, and in greyhound racing so that
there are monitoring and banning mechanisms in place and a high
degree of regulation.
Strychnine at the Olympics
Thomas Hicks, an American born in England on January 7, 1875, won
the Olympic marathon in 1904. He crossed the line behind a fellow
American, Fred Lorz, whose concept of marathon-running extended to riding
half the way in a car thereby getting himself disqualified.
However, Hicks was also aided by outside help. His trainer,
Charles Lucas, pulled out a hypodermic and came to his aid as his
runner began to struggle.
I therefore decided to inject him with a milligram of
sulphate of strychnine and to make him drink a large glass
brimming with brandy. He set off again as best he could [but] he
needed another injection four miles from the end to give him a
semblance of speed and to get him to the finish.
The use of strychnine, far from being banned, was thought
necessary to survive demanding races, says the sports historian
Alain Lunzenfichter. The historian of sports doping, Dr
Jean-Pierre de Mondenard, said:
It has to be appreciated that at the time the menace
of doping for the health of athletes or of the purity of
competition had yet to enter the morals because, after this
marathon, the official race report said: The marathon has shown
from a medical point of view how drugs can be very useful to
athletes in long-distance races.
Hicks was, in the phrase of the time, "between life and death"
but recovered, collected his gold medal a few days later, and
lived for almost 60 more years, although he never again took part
Benzedrine ("speed") is the trade name of the racemic mixture of
amphetamine (dl-amphetamine, (±)-1-phenylpropan-2-amine).
From as early as 1928 it was marketed under this brandname in the USA
by Smith, Kline and French in the form of inhalers. Benzedrine
was used to enlarge nasal and bronchial passages and it is
closely related to other stimulants produced later, such as
dextroamphetamine (d-amphetamine) and methamphetamine.
The Council of Europe says it first appeared in sport at the
Berlin Olympics in 1936. Its perceived effects gave it the street
name "speed". British troops used 72 million amphetamine tablets
in the Second World War and the RAF got through so many that
"Methedrine won the Battle of Britain" according to one report.
The problem was that amphetamine leads to a lack of judgement and
a willingness to take risks, which in sport could lead to better
performances but in fighters and bombers led to more crash landings
than the RAF could tolerate. The drug was withdrawn but large stocks
remained on the black market. Amphetamine was used legally as an aid
It is claimed that racemic amphetamine on the street is typically
only about 10% pure.
Benzedrine and its sister drugs have been irresistible in
cycling. In November 1942, the Italian cyclist Fausto Coppi took
"seven packets of amphetamine" to beat the world hour record on
the track. In 1960, the Danish rider Knud Enemark Jensen
collapsed during the 100 km team time trial at the Olympic Games
in Rome and died later in hospital. The autopsy showed he had
taken amphetamine and another drug, Ronicol, which dilates the
blood vessels. The chairman of the Dutch cycling federation, Piet
van Dijk, said of Rome that "dope - whole cartloads -[were] used
in such royal quantities.
2003 article on Drugs and Sport listed 10 drug scandals
A recent news item
on DEPEA in sports supplements has generated a media frenzy...
- E. German athletes and government sponsored cheating - see
the Wikipedia article - Doping in East
- 1983 Pan Am Games: Dawn of drug testing
- The U.S. Track and Field coverups
- Canada's shame: Ben
- Last to first: Irish swimmer Michelle
- Fake dynasty: Chinese swim team
- Tour de France: Whatever it takes
- Baseball: Home runs in bulk
- Cross country skiing and doping: a Nordic tradition
- Nandrolone goes for the Grand Slam
of athletes named in doping cases for using prohibited
substances has been compiled as well as a list of other
sportspeople who have been involved in doping offences. For
Jamaica there are about 25 people listed including Ben
Johnson who was born in Falmouth, Jamaica and emigrated to
Canada at age 15.
Oxilofrine - methylsynephrine
A 2009 case includes the
US-based Brazillian cyclist Flavia Oliveira.
4-[1-Hydroxy-2-(methylamino)propyl]phenol or oxilofrine
"Although initially uncertain as to how oxilofrine entered her body, Ms. Oliveira
now believes that her positive test was the result of her consumption of a dietary
supplement in capsule form known as Hyperdrive 3.0+. Ms. Oliveira asserts that,
before she began taking any of the Hyperdrive 3.0+ capsules, she researched the
ingredients listed on the product's label by examining the Prohibited List and
consulting the USA Cycling and USADA websites, and determined that none of
the listed ingredients were prohibited. Assuming the supplement was safe to
ingest, she began taking it in early 2009 and continued to take it, approximately
on a daily basis, up to and including June 19, 2009, the day she provided the urine
sample that tested positive for oxilofrine. According to the product's current list
of ingredients, Hyperdrive 3.0+ contains "methylsynephrine", a substance that
does not appear on the Prohibited List, but one which the parties agree has the
same chemical formula and structure as oxilofrine."
She was suspended for two years, since the arbitrator found that
Oliveira was sufficiently at fault to warrant the full penalty.
This was later reduced to 18 months.
details of the Arbitration Proceeding are available on-line.
Wilhelm Schanzer, director of Germany's official dope testing laboratory at the
German Sports University in Cologne, says that oxilofrine is easy to detect,
making it risky to take deliberately. Also, it is one of the weaker stimulants.
Schanzer's lab analysed 634 supplements from 13 countries and found that
15 per cent contained banned substances. He says there have been other
recent positive tests for oxilofrine. Following a bout in Germany on
1 February 2013, the Australian boxer Sam Soliman was found to have taken
oxilofrine, but blamed it on a supplement drink called "Black Bombs".
Note that both Asafa Powell and Sherine Simpson tested positive for oxilofrine
at the June Jamaican National Championships (announced on 14th July 2013).
Stanozolol, commonly sold under the name Winstrol (oral), Tenabol
and Winstrol Depot (intramuscular), was developed by Winthrop
Laboratories in 1962. It is a synthetic anabolic steroid derived
from testosterone, and has been approved by the FDA for human
stanozolol and nandrolone
Unlike most injectable anabolic steroids, stanozolol is not esterified and
is sold as an aqueous suspension, or in oral tablet form. The drug has a
high oral bioavailability, due to a C17 α-alkylation which allows the
hormone to survive first-pass liver metabolism when ingested. It is because
of this that stanozolol is also sold in tablet form.
Stanozolol is usually considered a safer choice for female bodybuilders
in that its anabolic effects predominate over its androgenic effects,
although virilization and masculinization are still very common even at
Stanozolol has been used in both animal and human patients for a number
of conditions. In humans, it has been demonstrated to be successful in
treating anaemia and hereditary angioedema. Veterinarians may prescribe
the drug to improve muscle growth, red blood cell production, increase bone
density and stimulate the appetite of debilitated or weakened animals.
Stanozolol is one of the anabolic steroids commonly used as a performance
enhancing drug and is banned from use in sports competition under the
auspices of the International Association of Athletics Federations (IAAF)
and many other sporting bodies. Stanozolol has also been used in US horse
Nandrolone (19-nortestosterone) is an anabolic steroid that may
be present naturally in the human body, albeit in minute
quantities of less than 0.4 ng/ml.
According to a supplement in the British Journal of Sports
Medicine, Br J Sports Med 2006;40(Suppl I):i25-i29. doi:
Nandrolone and other 19-norsteroid potent anabolic
steroids have been prohibited in sports for 30 years. The
detection of the main urinary metabolite (19-norandrosterone) in
amounts greater than 2 ng/ml constitutes an adverse analytical
finding. The presence in nutritional sport supplements of
steroids not listed on the label has undoubtedly resulted in
positive tests, but inadvertent consumption of meat containing
residues of hormonal treatment should not realistically cause
apprehension. Although highly improbable, athletes should
prudently avoid meals composed of pig offal in the hours
preceding the test since the consumption of edible parts of a
non-castrated pig, containing 19-nortestosterone, has been shown
to results in the excretion of 19-norandrosterone in the
Nandrolone and some of its metabolites.
The principal urinary metabolites formed following the
administration of 19-nortestosterone, were rapidly
identified as 19-norandrosterone (3α-hydroxy-5α-androstan-17-one),
and 19-norepiandrosterone (3β-hydroxy-5α-androstan-17-one).
These same metabolites are produced from "prohormones", 19-norandrostenedione
and 19-norandrostenediol, often referred to as precursors of nandrolone.
When orally administered, the metabolites are rapidly excreted in the
initial hours following administration and for several days they can be
easily detected in the urine.
Nandolone Mystery and Fact from FIFA
In recent years, there have been numerous doping cases involving nandrolone
that have led to various hypotheses concerning the origin of nandrolone
metabolites found in the urine of athletes. Several factors have been
identified that might influence a positive finding. For example, physical
effort can have different, but certainly no systematic effects, on the
excretion of nandrolone metabolites, depending on an individual's metabolism.
A natural source for production within the body may be a possibility.
Former world 100m champion Tyson Gay tested positive for a banned steroid
from a May 16, 2013 out-of-competition test that used
The label on the cream Gay is believed to have used apparently stated
"Testosterone/DHEA Creme" and listed testosterone and DHEA among its ingredients.
DHEA is a hormone converted in the body to testosterone, and both DHEA and
testosterone are banned for Olympic athletes. Two other listed ingredients,
IGF-1 and somatropin - another name for human growth hormone - are also forbidden.
According to athletes and coaches who spoke with Gay about the cream,
Gay insisted that Clayton Gibson, an Atlanta-based anti-ageing doctor,
had told him that the product was "all natural" and that
NFL clients had used it and passed drug tests.
The label on the jar is supposed to have read "100% All Natural."
David Howman, director general of the World Anti-Doping Agency,
said it is "staggering" that an athlete today would use a supplement
that so clearly advertised its banned ingredients.
"That's where it falls into the level of negligence" he said.
Human Growth Hormone
Growth hormone (GH) occurs naturally in the human body where it is called HGH.
Growth hormone (GH) is a peptide hormone that stimulates growth, cell
reproduction and regeneration in humans and other animals. Growth hormone
is a 191-amino acid, single-chain polypeptide that is synthesized, stored,
and secreted by the somatotroph cells within the lateral wings of the
anterior pituitary gland.
Use of exogenous human growth hormone (HGH), through needle injection,
was originally for medical purposes until athletes began abusing HGH
with the goal of increasing their abilities. Before recombinant human
growth hormone (rHGH) was developed in 1981, HGH was only available
from cadavers. The arrival of rHGH combined with other biotech
advancements has increased the availability of HGH on both the
legitimate and black markets. In 1989 the International Olympic
Committee became the first to brand human growth hormone a banned
substance. Even though supplying human growth hormone for athletic
purposes is illegal in the U.S., over the past decade it appears that
abuse of HGH has spread to athletes of all levels. This is fueled at least
in part by the fact that HGH is more difficult to detect than most other
performance enhancing drugs, such as anabolic steroids. Athletes competing
in power sports, bodybuilding, professional wrestling, mixed martial arts,
swimming, baseball, strength sports, track and field, cycling, soccer,
weight lifting, and endurance sports have been said to abuse human
growth hormone, often in combination with other performance enhancing
drugs such as anabolic steroids, testosterone, products claiming to
enhance HGH, and EPO.
Traditional urine analysis could not detect doping with HGH, so early bans
were unenforceable until the early 2000s when blood tests that could
distinguish between natural and artificial HGH began to be developed.
Blood tests conducted by WADA at the 2004 Olympic Games in Athens,
Greece targeted primarily HGH. This use for the drug is not approved
by the FDA; GH is legally available only by prescription in the
WADA has information on
related to HGH
Is a urine test for HGH likely to be developed?
Can blood samples be stored?
- According to the overwhelming majority of international experts,
the blood matrix is the most reliable matrix for the detection of hGH.
- HGH in urine is found in extremely small quantities (less than 1% than
that found in blood).
- In the view of international scientific experts, efforts to develop a
reliable urine test for HGH would require significant resources and time,
and chances of success appear remote
- Freezing liquid fraction of blood (serum or plasma) is a scientifically
acceptable solution that allows for the preservation of substances in
samples for future testing and detection.
- Research has shown that HGH is very stable in frozen serum or plasma.
- WADA encourages anti-doping organizations under the World Anti-Doping
Code to store blood samples when relevant.
- Storing serum or plasma for future testing has a significant deterrent effect.
- The World Anti-Doping Code makes it possible to open a disciplinary
proceeding within eight years from the date an anti-doping rule
2011 Student Presentations and Reports
Much of the information in these course notes has been sourced
from Wikipedia under the Creative Commons License. Students
taking this course will be expected to contribute to Wikipedia as
a part of their course assignments.
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last modified 21st February 2014.