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ECHA InfoCard | 100.006.067 |
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Formula | C10H15NO2 |
Molar mass | 181.235 g·mol−1 |
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Oxilofrine (also known as methylsynephrine, hydroxyephrine, oxyephrine, and 4-HMP) is a substituted phenethylamine stimulant drug [2] chemically related to ephedrine and to synephrine.
Oxilofrine is currently a World Anti-Doping Agency (WADA) prohibited substance when used in competition. [3] It has been found as an adulterant in some dietary supplements. [4] [5] Even after receiving warning letters from the FDA, [6] some sports and weight loss supplement companies continue to use oxilofrine as an undeclared ingredient in their products despite it being prohibited. [7]
Oxilofrine was originally developed in the 1930s as a cardiac stimulant. Trade names included Suprifen (Bayer) and, combined with an adenosine-containing standardized organ extract, Carnigen (Hoechst AG). [4]
In combination with normethadone, it was marketed as a cough suppressant under the trade name Ticarda. As of 2021, this formulation was still manufactured in Canada by Valeant and sold as Cophylac. [8]
Several other stimulants and vasodilators were developed as chemical derivatives of oxilofrine, such as buphenine. [9] [10]
Several doping cases involving oxilofrine have been publicized, including:
Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.
In competitive sports, doping is the use of banned athletic performance-enhancing drugs by athletic competitors, as a way of cheating. The term doping is widely used by organizations that regulate sporting competitions. The use of drugs to enhance performance is considered unethical, and is prohibited by most international sports organizations, including the International Olympic Committee. Furthermore, athletes taking explicit measures to evade detection exacerbate the ethical violation with overt deception and cheating.
Asafa Powell, CD is a retired Jamaican sprinter who specialised in the 100 metres. He set the 100 metres world record twice, between June 2005 and May 2008 with times of 9.77 and 9.74 seconds. Powell has consistently broken the 10-second barrier in competition, with his personal best of 9.72 s ranking fourth on the all-time list of men's 100-metre athletes. As of 1 September 2016, Powell has broken the ten-second barrier more times than anyone else—97 times. He currently holds the world record for the 100-yard dash with a time of 9.09 s, set on 27 May 2010 in Ostrava, Czech Republic. At the 2016 Rio Olympic Games, he won a gold medal in the 4 x 100 metres relay.
Sherone Simpson is a Jamaican track and field sprint athlete. She is a gold medalist in the 4 × 100 m relay from the 2004 Olympics and silver medalist in 2005 World Championships and now is the silver medalist in the individual event at the 2008 Summer Olympics, after she tied for second with Kerron Stewart in a photo finish.
Trimetazidine is a drug for angina pectoris sold under many brand names. Trimetazidine is described as the first cytoprotective anti-ischemic agent developed and marketed by Laboratoires Servier (France). It is an anti-ischemic (antianginal) metabolic agent of the fatty acid oxidation inhibitor class, meaning that it improves myocardial glucose utilization through inhibition of fatty acid metabolism.
Clenbuterol is a sympathomimetic amine used by sufferers of breathing disorders as a decongestant and bronchodilator. People with chronic breathing disorders such as asthma use this as a bronchodilator to make breathing easier. It is most commonly available as the hydrochloride salt, clenbuterol hydrochloride.
Performance-enhancing substances, also known as performance-enhancing drugs (PEDs), are substances that are used to improve any form of activity performance in humans. A well-known example of cheating in sports involves doping in sport, where banned physical performance-enhancing drugs are used by athletes and bodybuilders. Athletic performance-enhancing substances are sometimes referred as ergogenic aids. Cognitive performance-enhancing drugs, commonly called nootropics, are sometimes used by students to improve academic performance. Performance-enhancing substances are also used by military personnel to enhance combat performance.
β-Methylphenethylamine is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.
Clostebol usually as the ester clostebol acetate, is a synthetic anabolic–androgenic steroid (AAS). Clostebol is the 4-chloro derivative of the natural hormone testosterone. The chlorination prevents conversion to dihydrotestosterone (DHT) while also rendering the chemical incapable of conversion to estrogen. Although usually used as an ester including clostebol acetate, clostebol caproate (Macrobin-Depot), or clostebol propionate (Yonchlon), unmodified/non-esterified clostebol is also reported to be marketed, under the brand name Trofodermin-S in Mexico.
Tuaminoheptane is a sympathomimetic agent and vasoconstrictor which was formerly used as a nasal decongestant. It has also been used as a stimulant.
Methylhexanamine is an indirect sympathomimetic drug invented and developed by Eli Lilly and Company and marketed as an inhaled nasal decongestant from 1948 until it was voluntarily withdrawn from the market in the 1980s.
Phenpromethamine, also known as N,β-dimethylphenethylamine, is a sympathomimetic nasal decongestant of the phenethylamine group. It was previously marketed as a nasal inhaler from 1943 through 1960 but is no longer available. The medication is a stimulant and is banned by the World Anti-Doping Agency. It has been detected in dietary supplements starting in the 2010s.
Enobosarm, also known as ostarine or MK-2866, is an investigational selective androgen receptor modulator (SARM) developed by GTx, Inc. for the treatment of conditions such as muscle wasting and osteoporosis, formerly under development by Merck & Company.
Doping, or the use of restricted performance-enhancing drugs in the United States occurs in different sports, most notably in the sports of baseball and football.
Flávia Maria de Oliveira Paparella is a Brazilian racing cyclist. She competed in the 2013 UCI Women's World Championship Road Race in Florence, as well as the 2014 UCI Women's Road World Championships in Ponferrada. She competed at the 2016 Olympic Games in Rio de Janeiro where she finished in seventh place, the highest placed finish for a Brazilian rider in any Olympic cycling event.
Ligandrol is a novel nonsteroidal oral selective androgen receptor modulator (SARM) for treatment of conditions such as muscle wasting and osteoporosis, discovered by Ligand Pharmaceuticals and under development by Viking Therapeutics.
The practice of doping in tennis involves the use of prohibited, performance-enhancing substances listed by the International Tennis Federation (ITF) and World Anti-Doping Agency (WADA). The practice is considered unsportsmanlike and unethical, with punishments for such offences ranging from official warnings to career bans, depending on the severity of the offence.
Doping in figure skating involves the use of illegal performance-enhancing drugs (PEDs), specifically those listed and monitored by the World Anti-Doping Agency (WADA). Figure skaters occasionally have positive doping results but it is not common. Bans can be enforced on figure skaters by the International Skating Union (ISU) and each country's individual skating federation. These bans can often be career ending due to the competitive nature of figure skating. A ban may be revoked if it can be proved that the skater tested positive for a prescribed medication. Some figure skaters will use PEDs to help with recovery time, allowing them to train harder and longer. Figure skating is an aesthetic sport that combines both athleticism and artistic licence, where weight-loss substances will have little effect on athletic performance but skaters may be perceived as more graceful and sleek, which is required for an athlete to be competitive.
Deterenol is a stimulant drug which acts as a beta agonist. It has been found as an ingredient of dietary supplement products, but is banned in most countries due to risk of cardiac arrest.