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Retro-anabolic steroids from the Netherlands

Normal anabolic steroids have a flat spatial structure. But in a patent filed in 1965, Dutch researchers devote over a hundred pages to describing a group of anabolics with a Z-shaped structure, has discovered.

Regular anabolic steroids are 10-beta, 9-alpha steroids. This means that the tenth carbon atom has a beta configuration and the ninth an alpha configuration. But the anabolic steroids in this patent are 10-alpha, 9-beta steroids. This is why they have a different spatial structure. Anabolics with a Z-skeleton are called retro-anabolics, and the Dutch wanted to claim the whole retro-steroids field when they filed their patent.

Retro-anabolic steroids from the Netherlands

Above you can see the molecular structure of normal testosterone. In retro-testosterone the molecule makes a downward turn at C9 if you go from right to left. At C10 the retro-molecule makes another turn to the left. That creates the Z-structure, which you can see below.

Retro-anabolic steroids from the Netherlands

If you want to know more about the structure of steroids, go to chapters Four and Five of the Anabolics Book.

The Dutch were able to make retro-anabolics because they were in possession of a natural substance with this kind of Z-structure. Reading the patent, this turns out to be lumista-4,22-dien-3-one. The researchers used this component to build dozens of retro-analogues of anabolic steroids known at the time.

For example, they made a retro-form of methandienone, but this was not an interesting compound. Methandienone is a steroid that has no progesterone effect and in low doses doesn't inhibit the natural production of testosterone that much. Retro-methandienone is also anabolic, does have a considerable progesterone effect and inhibits the body's own production of testosterone severely.

Most of the hormones that the Dutch researchers made were anti-hormones. And most had a much weaker effect than the regular analogues. But in the table on page 106 there are three anabolic steroids listed that might have been pretty interesting.

The three retro-anabolic steroids had an anabolic effect but not an androgenic effect, and had few other side effects. They were compounds 28, 49 and 66: 2-methyl-retro-testosterone, retro-androstanediol and 2-oxymethylene-retro-testosterone.

As far as we know, retro-anabolic steroids have never made it onto the market. The company that the Dutch worked for, Duphar based in Weesp, probably directed its attention in a different direction and never did anything with these retro anabolic steroids.

US Patent 3,198,792.