T Nation

Esterified 4-AD interest...

Are people still interested in this 'round here? I know there was a big thread going a while back. It may be available quite soon…

4-AD-EC powder? Bring it on…

No, like 4-ad diacetate, dipropionate…more oil soluble than 4-ad-ec if you know what I mean.

At least in the case of the diacetate, I know that an individual in the industry (self-proclaimed as the “father” of such and such, etc, etc… from this you may guess whom I mean) was unable to produce it in any sort of reasonable purity, even by his company’s low standards, and asked me for my opinion on the matter and any possible advice on his manufacturing process. What I advised was that when one has steroids that are a mixture of isomers, e.g. 3alpha and 3beta, and the compounds are fairly low melting point, then there is a strong tendency for them to “oil out” rather than crystallize, or to produce a soft solid. When you don’t get true crystals then you don’t get the increase in purity usually attendent with recrystallization.
Besides this, there was no real point to the diacetate for an oral product, I advised, since it would be cleaved prior to absorption.

By the way, while the ethylcarbonate ester does have a higher melting point than would be desired for an oil injectable (resulting in low solubility) this property also production of high purity product feasible.

Well I do know what you are talking about, I believe I used this persons 4-ad as a starting material and would say it was about 70% pure. THe recrystallization I have done produce a talc like product, and even with very slow recrystallization no well defined crystals are formed. The purity of what I have made seem ok, melting point wise anyway. Perhaps small microcrystalline eutectic mixtures are formed that don’t grow very well. I am just guessing on that. I would like to get an assay done to see if the %purity, hopefully it is 97% or higher.
Bill, since I hopefully have your attention, 2 q’s. Why is 1-test irritating? Boldenone and dht are not, and those are very closely related, also primo and masteron. Is it the steroid or an impurity? Any thoughts on adding a long ester like cyp help with the irritation?
2nd Not trying to shoot you down, I repect your work, did you base the ec ester from a shiongi product? I gotta believe you did just because you were talking about the cyclopentyl ethers just like they had, and recenly I see that they had an ethylcarbonate product as well. No offense but others at the mag made it sound like you “invented” it specifically for this purpose. Thanks.

Unfortunately, I’m now working at home quite some distance from my old lab at the University of Florida, and relatively simple things such as performing column chromatography on 17b-hydroxy-5a-androst-1-
ene-3-one (androst-1-ene, or as you call it, “1-test” though it is not a testosterone) so as to have a pure sample with which to give a simple final answer to your question, aren’t so feasible. I expect it is impurity because of the points you make, because different samples seem different, and because every other time with “prohormones” that this sort of thing has come up, whether it be bitter taste or what have you, it’s always been impurity to blame.

No, I didn’t obtain any ideas from Shiongi.
The cyclopentenyl ethers were derived from the work of Ercoli. If Shiongi has done anything with carbonate esters of steroids I was not aware of it. It was my own idea based on my own knowledge of carbonate esters obtained from study of prodrug design, combined with knowledge of steroid metabolism, as well as the fact that in my academic research I used carbonate esters as a protecting group in synthesis of 3-alkylcarbonyloxymethyl derivatives of 5-fluorouracil, and so had close familiarity with them.

The patent search we had done did not find
anyone else having anticipated me on using this type of ester to improve oral delivery of the kinds of steroids we claim. That I invented it specifically for this purpose is to my knowledge correct; if instead it is a “reinvention” then this isn’t known to us.

In fact, another in the industry claiming to be an expert in the field insisted I was wrong and the method would not work. So it is not an obvious one.

But that carbonate esters already were known to organic chemistry and pharmaceutical science as a type of promoiety? Of course and I hadn’t thought T-mag had implied differently.

It’s interesting how similar things develop independently of each other. No the shionogi EC ester is not used for the same steroids you are using it for, I didn’t mean to imply that. Just so you know that I’m not blowing smoke up your ass:
2a,3a-Epithio-17b-ethoxycarbonyloxy-5a-androstane. Tokutake, Hakuo.
(Shionogi and Co., Ltd.). Jpn. Tokkyo Koho (1972), 2 pp.

Patent No. Kind Date Application No. Date
JP 47007545 B4 19720303 JP 19670921


The title compd. (I), useful as an anabolic steroid, was prepd. in 83%
yield by treating the corresponding 17b-hydroxy compd. with di-Et
pyrocarbonate and pyridine for 5 hr at 26?followed by stirring at pH 10.