Steroid Chemistry Question

[Newport Surfer]

I am in no way a chemist but I have a question...

Well most of us know by now that Ergomax LMG is exactly, or close in structure to DMT... it is known as 17-methyl-5alpha-androst-2-en-17beta-ol.

Now my question related to DHT. With a chemical compound contains "5alpha" does that mean that it converts to a high degree of DHT? Or is my thinking way off?

[Andrew99]

Well, I am a chemist and I'd be happy to look into it, but I don't know what you are referring to by DHT. Pls clarify and I'll give my opinion on whether 17-methyl-5alph-aandrost-2-en-17 beta-ol converts to it.

[Newport Surfer]

I think I found my answer..

"5ar (5 alpha reductase)"

This compound is responsible for converting testosterone to DiHydrotestosterone (DHT)

An acronym for DiHydroTestosterone, the most potent of the human Androgens. DHT is converted from Testosterone via the enzyme 5α-Reductase, this conversion is mono-directional.


Now can you please clarify this for me. when it says the conversion is monodirectional what does that mean? I understand this means it is fairly androgenic but by its place in the chemical structure can you tell how much of a conversion to DHT that it has?

[Andrew99]

It means that under physiological conditions the only reaction which takes place is the reducing one, and that utilizes 5-ar as an enzyme, presumably to speed up the kinetics. DHT is different from T as it has two extra hydrogens. The 5-ar kicks off the hydrogens and presumably a double bond forms, though I don't have the structure in front of me. Hydrogenating a double bond is an oxidation reaction, which apparantly does not occur in the body. I'm not a biochemist, so I can't tell you why, but thats what the "monodirectional" statement means.

[chlaxman]

I think I found my answer..

"5ar (5 alpha reductase)"

This compound is responsible for converting testosterone to DiHydrotestosterone (DHT)

An acronym for DiHydroTestosterone, the most potent of the human Androgens. DHT is converted from Testosterone via the enzyme 5α-Reductase, this conversion is mono-directional.


Now can you please clarify this for me. when it says the conversion is monodirectional what does that mean? I understand this means it is fairly androgenic but by its place in the chemical structure can you tell how much of a conversion to DHT that it has?
You get that off pubmed? I think I read the same study a few days ago.

[Brinn]

An acronym for DiHydroTestosterone, the most potent of the human Androgens. DHT is converted from Testosterone via the enzyme 5α-Reductase, this conversion is mono-directional.


Now can you please clarify this for me. when it says the conversion is monodirectional what does that mean?
It means that DHT is not converted to testosterone. Many reaction can happen in both directions depending on things like pH or concentrations of product already present.

[Newport Surfer]

You get that off pubmed? I think I read the same study a few days ago.

I forget what site it was on... I was just searching around.