Epitestosterone

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Structural formula
Structure of epitestosterone
General
Non-proprietary name Epitestosterone
other names

17 α -hydroxy-androst-4-en-3-one

Molecular formula C 19 H 28 O 2
External identifiers / databases
CAS number 481-30-1
EC number 641-984-7
ECHA InfoCard 100.169.813
PubChem 10204
ChemSpider 9789
DrugBank DB07768
Wikidata Q416852
properties
Molar mass 288.43 g mol −1
safety instructions
GHS labeling of hazardous substances
08 - Dangerous to health

Caution

H and P phrases H: 341
P: 280
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Epitestosterone is a natural steroid , the inactive 17 α - isomer of the sex hormone testosterone . It is believed that the body produces epitestosterone in a similar way to testosterone. A 1993 study showed that about 50% of the amount of epitestosterone in men is produced in the testes , but the exact process of how this is produced is still being researched. Epitestosterone accumulates in the fluid from breast cysts and in the prostate . Epitestosterone levels are highest in young men. In adulthood, most healthy men have a testosterone to epitestosterone ratio (T / E ratio) of around 1: 1.

Epitestosterone and testosterone

It has been shown that the exogenous supply of testosterone does not affect the epitestosterone level in the blood. For this reason, tests that determine the ratio of testosterone to epitestosterone in the urine are used as a doping test in athletes. In most people, the ratio of testosterone to epitestosterone (T / E ratio or T / E ratio) in the urine is about 1: 1; Occasionally, however, T / E ratios of 4: 1 are found, in some people even T / E ratios of up to 10: 1 can be normal.

Epitestosterone has not been shown to have any performance enhancing effects, but epitestosterone delivery can be used to mask high testosterone levels if the normal T / E ratio test is used. Therefore, many sports federations prohibit the use of epitestosterone as a masking agent for testosterone.

The American athlete Mary Decker failed a T / E test in 1996 because her T / E ratio was more than 6: 1, the limit then valid. She appealed that the contraceptive pill could give false T / E test results, but the appeals court ruled against her.

Floyd Landis was stripped of his Tour de France tour victory after a second test showed an increased T / E ratio. The Floyd Landis A sample test results showed a T / E ratio of 11: 1. His testosterone level was within the normal range, so the problem was a deviating epitestosterone level. Landis won the 17th stage of the tour; however, tests carried out immediately after the award ceremony showed a T / E ratio of 11: 1, more than double the 4: 1 limit (recently downgraded from the previous 8: 1 and 6: 1 limits). Landis has emphatically denied the allegation, referring to scientific data that testosterone cannot improve an athlete's performance unless it is taken regularly over a long period of time.

Individual evidence

  1. a b Epitestosterone data sheet from Sigma-Aldrich , accessed on March 30, 2011 ( PDF ).

See also