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20-Hydroxyecdysone (Molecule of the Month for September 2008)

Ecdysterone, 20E



20-Hydroxyecdysone (ecdysterone or 20E) is a naturally occurring ecdysteroid hormone which controls the ecdysis (moulting) and metamorphosis of arthropods. It is therefore one of the most common moulting hormones in insects, crabs, etc. It is also a phytoecdysteroid produced by various plants, including Cyanotis vaga, where its purpose is presumably to disrupt the development and reproduction of insect pests. Ecdysone and 20-hydroxyecdysone (20E) regulate larval molts, onset of puparium formation, and metamorphosis. Being that these hormones are hydrophobic, they traverse lipid membranes and permeate the tissues of an organism.

In arthropods, 20E acts through the ecdysone receptor. Although mammals lack this receptor, 20E does appear to affect mammalian (including human) physiology, but there is disagreement over the details of its effects. 20E is an ingredient of some preparations that aim to enhance physical performance. When first isolated, there was little interest from the commercial sector due to the lack of a cost-effective way to extract or synthesize the chemical. However, recent breakthroughs have meant that it can now be isolated in an extremely concentrated form. This has led to experimentation with its use as an anabolic steroid in sport and bodybuilding.

Despite lacking FDA approval it has proven to be moderately successful as a commercial product in the countries in which it is produced, likely due to its efficacy in promoting muscle growth and fat loss, and lower frequency of side-effects usually associated with anabolic steroids. Such side effects are still fairly common, however, as a result of increased testosterone and DHT production, and include androgenic changes in females such as growth of facial and body hair and deepening of the voice, as well as gastrointestinal problems for both sexes, such as nausea, bloating, and diarrhoea.

Formal Chemical Name (IUPAC)
(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-17-((2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl)-2,3,4,5,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6(10H)-one

References

http://en.wikipedia.org/wiki/Ecdysterone

Picture of 20-Hydroxyecdysone 3D model

click on the picture of  20-Hydroxyecdysone above to interact
with the 3D model of the
20-Hydroxyecdysone structure
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Picture of 20-Hydroxyecdysone

C27 H44 O7



Update by Karl Harrison
(Molecule of the Month for September 2008 )

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