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 public.

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 in athletics.

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 to slimming.

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.

A CBC 2003 article on Drugs and Sport listed 10 drug scandals
  1. E. German athletes and government sponsored cheating - see the Wikipedia article - Doping in East Germany
  2. 1983 Pan Am Games: Dawn of drug testing
  3. The U.S. Track and Field coverups
  4. Canada's shame: Ben Johnson
  5. Last to first: Irish swimmer Michelle Smith
  6. Fake dynasty: Chinese swim team
  7. Tour de France: Whatever it takes
  8. Baseball: Home runs in bulk
  9. Cross country skiing and doping: a Nordic tradition
  10. Nandrolone goes for the Grand Slam
A recent news item on DEPEA in sports supplements has generated a media frenzy...

A list 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

4-[1-Hydroxy-2-(methylamino)propyl]phenol or oxilofrine
A 2009 case includes the US-based Brazillian cyclist Flavia Oliveira.
"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. More 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).

Arnold woman body builder

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 use.

nandrolone and stanozolol
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 low doses.

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 racing.

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: 10.1136/bjsm.2006.028027
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 following hours.
metabolites of nandrolone
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), 19-noretiocholanolone (3α-hydroxy-5β-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.

Tyson Gay
Former world 100m champion Tyson Gay tested positive for a banned steroid from a May 16, 2013 out-of-competition test that used GC-IRMS.
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.

human growth hormone
Human Growth Hormone (IHGU).

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 United States.

WADA has information on detection and other facts related to HGH
Is a urine test for HGH likely to be developed?
Can blood samples be stored?

2011 Student Presentations and Reports
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Created September 2011. Links checked and/or last modified 21st February 2014.