How many different steroids can one make from 1-test....

[Andy13]

It was just for giggles and laughs, nothing seriously. I didn't purify it and certainly did not use it. There was probably a mild case of oxidation.

Sounds interesting. Give me the reference.

How do you know you were successful? Did you do MP or TLC at least?

The thing about home synthesis that is just scary is there are no real home-based analytical methods to see how much garbage is in your product. The closest you could come would be to run the most purified stuff through a silica column.. That alone is a real pain in the ass.

Andy

 

[variation]

I would think a simple method would be to test melting point, easily done, and you can match results to the actual melting point of the hormone+ester.

 

[balls]

Everything that is made through transformations such as those outlined by spidey, should be purified before use (critical if injecting). Column chromatography is the best idea. However, if the reaction is very clean, you could get away with a recrystallisation, followed by some sort of analysis to ensure purity.

 

[Andy13]

Everything that is made through transformations such as those outlined by spidey, should be purified before use (critical if injecting). Column chromatography is the best idea. However, if the reaction is very clean, you could get away with a recrystallisation, followed by some sort of analysis to ensure purity.

Even seasoned Organic Chemists groan when you mention "column chromatography."

 

[Spidey]

Re: Re: How many different steroids can one make from 1-test....

No references for these?

With only a light, once over of these procedures.. I question step 2 in your ox synthesis. The 17 alkylation is NOT stereo specific. Alkylation a la Grignard with methyl magmesium iodide would give 17-alpha and beta methyl group.. As far as I know, all AAS are 17 ALPHA alkylated.

If the two products could be separated, I think this one looks reasonably feasible.

Andy

I know. I said I was through here at EF but I have to post one last time, LOL. I have been checking back every week or so to see if my request to have myself and my posts deleted has been honored. Obviously, not yet.

Andy, the grignard addition to the 17-carbonyl is quite selective for the alpha isomer due to steric constraints imposed by the 3-D shape of the steroid molecule. The beta face of the carbonyl is sterically shielded. How do you think 17-AAS were prepared in the first place? The chemists of the 40's and 50's did not have the same synthetic tools we have today. They used grignards to install 17-alkyl groups and it just so happened that the alpha isomer was the major product. Thus, 17-AAS were born. Grignards (or alkyl lithiums) are likely STILL the method of choice for preparing them.

Also, seasoned chemists do not shudder at the prospect of column chromatography. It's quite simple really. A column only takes about 15 to 30 minutes to run if you know what you are doing. I do them almost daily, sometimes several a day.

Someone was correct above though when they noted that any of these syntheses would require purification of the final products. I put these out there as an academic exercise, not as something feasible for the average "bathtub" chemist. I believe this was noted at the top of the thread.

If anyone has any questions or critisisms in the future, please feel free to email me at [email protected]

 

[jacshelb]

OXANDROLONE (Anavar)

Step 1: Starting with 1-test base, the 3-one is protected as the ethylene ketal as in the above synthesis of methandrostenolone.

Step 2: The 17-OH is oxidized to a 17-one with chomium VI reagent.

step 3: The 17-methyl is attached with methyl magnesium iodide and the crude reaction mixture is treated with water and acid to quench the reaction and remove the ketal protecting group. The product is 17-methyl-1-test.

Step 4: the 17-methy-1-test is treated with ozone in methanol and then NaOH is added. This allows the purification of the intermediate by recrystallization of the sodium salt. The result is that the double bond is cleaved to give a carboxyolic acid (salt) on one side and an aldehyde on the other. The salt is dissolved in water and acidified to pH=4. NaBH4 is added to reduce the intermediate aldehyde. The resulting alcohol will spontaniously close with the carboxylic acid to give the desired lactone ring. The product is oxandrolone.

With the advent of 1-methyl test, wouldn't step four be the only necessary step? Or is 1-methyl test different from 17-methyl-1-test?

Heck of a good thread. Very interesting reading.


Jacob

 

[MACHI]

I know I'm resurrecting and old thread here but.......

I just joined the board after being referred a while back by someone. I'm a biochem major and heavily into bodybuilding. This thread is awesome. I've been on boards like meso and AR for awhile but they didn't have much of the nitty gritty science discussions I was looking for. I have recently been looking for as much info as possible on this subject myself (steroid synthesis from PH's). I start research soon and I'm thinking of trying some of the proposed methods and then subjecting the results to HNMR, CNMR, IR spec, GC/MS, and automated Coulmn chromatography (the thing is VERY fast and easy) as I will have access to all of them. What do you guys think of this? Will I be able to easily identify my product with the combined onslaught of these tools? lol

I'm curious too - How many other people here are org/bio chemists or working in the industry?

 

[chem_kid]

I'm in the same boat as you bro. I am a biochemist working as a computer programmer right now. I would like to perform a synthesis of testosterone from DHEA for academic reasons naturally. Any ideas for referrences? You do not learn a wealth of hormone synthesis chemistry in any biochem program as you know. What I am wondering is - the impurities. What are they? Do you have any idea? Thanks.

 

[lanky]

I'm in the same boat as you bro. I am a biochemist working as a computer programmer right now. I would like to perform a synthesis of testosterone from DHEA for academic reasons naturally. Any ideas for referrences? You do not learn a wealth of hormone synthesis chemistry in any biochem program as you know. What I am wondering is - the impurities. What are they? Do you have any idea? Thanks.

chem_kid, i have a GOOD secondary documentation resources for you, ive been saving it for someone who has significant scientific interest. i cant post it here so ill pm it to you later this week. it makes the Merk handbook look like a dr. seus book.

 

[Andy13]

I'm in the same boat as you bro. I am a biochemist working as a computer programmer right now. I would like to perform a synthesis of testosterone from DHEA for academic reasons naturally. Any ideas for referrences? You do not learn a wealth of hormone synthesis chemistry in any biochem program as you know. What I am wondering is - the impurities. What are they? Do you have any idea? Thanks.

Unlike the prohormones banned recently, (those tied to athletics), DHEA is one the gov't wouldn't dare touch (fearing the wrath of million outraged geriatrics).

So it’s a good choice of starting material for your academic project, except that synthesis of 17-methyl testosterone, (rather than testosterone itself) may prove to be more feasible. The problem is the reduction of the 17-keto function of DHEA. I am not aware of a reducing agent that, upon reduction of the keto, would yield purely the beta-hydroxy isomer. On the other hand, treatment of DHEA with methyl magnesium iodide followed by Oppenhour oxidation would yield methyl test in what would seem to be a relatively straightforward procedure.

Andy