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

[Spidey]

This thread is strictly for entertainment purposes. I do not use or condone the use of illegal drugs. I have not performed these syntheses, nor will I consider doing so.


BOLDENONE CYPIONATE (fast acting EQ)

Step 1: 1-Test cyp is brominated in the 4 position with 2,4,4,6-tetrabromocyclohexa-2,5-dione in ether with catalytic HCl. The product is 4-bromo-1-testosterone cypionate. There are other methods to achieve this bromination as well but this one should work very cleanly with a minimum of side reactions.

Step 2: the bromide is eliminated to give the 4,5-double bond by stirring the above product in DBU for 10 to 20 minutes. The overall yield of bold cyp should be around 75 to 80%

METHANDROSTENOLONE (dbol)

Step 1: The bold cyp from above is stirred in boiling benzene with ethylene glycol and catalytic acid. A Dean-Stark trap should be used to remove water as it is formed. This protects the 3-one as an ethylene ketal.

Step 2: The above protected bold cyp is stirred in boiling methanol/water with NaOH to remove the cyp ester.

Step 3: The 17-OH is oxidized to a ketone with any of a variety of chromium VI reagents.

Step 4: The above 17-one is reacted with methyl magnesium iodide. The reaction is quenched with water and acid. Heating the mixture with the water and acid will remove the ethylene ketal as well, leaving you with methandrostenolone.

METHENOLONE CYPIONATE (Primobolin, although real primo is the enanthate, not the cypionate, I expect little difference in function.

Step 1: 1-Test cyp is reacted with tetramethyl dilithium pentacuprate (formed in-situ from CuI and meLi). The reaction is quenched with liquid bromine. The product is 2-bromo-1-methyl-DHT.

Step 2: The bromine is eliminated to give back the 1,2-double bond by stirring with DBU as in the synthesis of bold cyp. The product is methenolone cypionate.

MESTEROLONE (proviron)

1-Test base is reacted with tetramethyl dilithium pentacuprate (formed in-situ from CuI and meLi). The reaction is quenched with water to afford mesterolone in a single step.

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.

OXYMETHYLONE (Anadrol)

17-methyl-1-test from above is reduced with lithium in liquid ammonia. The ammonia is carefully evaporated under a dry N2 atmosphere to give a dry, crystalline enolate. The enolate is dissolved in dry THF and treated with N-formylmorpholine to give oxymethylone as the product.

DROMOSTANOLONE propionate (Masterone)

Step 1: 1-test base is reduced with lithium in liquid ammonia. The ammonia is carefully evaporated under a dry N2 atmosphere to give a dry, crystalline enolate. The enolate is dissolved in dry THF and treated with methyl iodide to install the 2-methyl group.

Step 2: the dromostanolone resulting from step 1 is esterified with propanoyl chloride and pyridine to afford the product, masterone.


Of course, since we all know that 1-test is bunk and isn't a REAL steroid to begin with, non of the derivatives above are REAL steroids either, LOL.

 

[Spidey]

Of course, there are easier ways to make some of those. I was trying to make all of them from 1-test.

Boldenone would be easier to make from 1,4-androstadiene-3,17-diol or the 17-cypionate thereof. One can currently purchase the powder legally in the USA but I think it will soon be illegal.

Anyway, just stirring 1,4-androstadiene-3,17-diol with manganese dioxide (MnO2) will oxidize the allylic 3-OH to a 3-ONE and VOILA, boldenone base in one step from a legal prohormone.

4-androstene-3,17-diol can be oxidized to testosterone the same way. If one were to start with the 17-cypionate of 4-androstenediol, test cyp would be the product.

Nandrolone can be made analogously from 19-nor-4-androstene-3,17-diol. MnO2 oxidations are extremely mild and clean reactions. It is unusual for any side reactions to occur at all.

 

[Toozee]

That's very informative.
Cool that you took the time to figure it up.

 

[Spidey]

LOL, I was bored

 

[Andy13]

God.. I hope nobody tries any of these for real..

No references?

 

[Sigmund Roid]

Nice tread, spidey

For boldenone, is it also possible to use 2,4,4,6-tetrabromo-2,5-cycohexadien-1-one?

BTW, In the past I used the MnO2 to make nandrolone, but my material (was a bit orange like). You think there are still some side-products made?

Another question, do you know how to make steranabol? That is methenolone but with the methyl group on the 2-position in stead of the 1-position.

 

[Andy13]

Nice tread, spidey

For boldenone, is it also possible to use 2,4,4,6-tetrabromo-2,5-cycohexadien-1-one?

BTW, In the past I used the MnO2 to make nandrolone, but my material (was a bit orange like). You think there are still some side-products made?

Another question, do you know how to make steranabol? That is methenolone but with the methyl group on the 2-position in stead of the 1-position.

Did you actually use your nandrolone? How did you assess its purity? Better yet, how did you purify it?

Andy

 

[Andy13]

METHANDROSTENOLONE (dbol)

Step 1: The bold cyp from above is stirred in boiling benzene with ethylene glycol and catalytic acid. A Dean-Stark trap should be used to remove water as it is formed. This protects the 3-one as an ethylene ketal.

Step 2: The above protected bold cyp is stirred in boiling methanol/water with NaOH to remove the cyp ester.

Step 3: The 17-OH is oxidized to a ketone with any of a variety of chromium VI reagents.

Step 4: The above 17-one is reacted with methyl magnesium iodide. The reaction is quenched with water and acid. Heating the mixture with the water and acid will remove the ethylene ketal as well, leaving you with methandrostenolone.

METHENOLONE CYPIONATE (Primobolin, although real primo is the enanthate, not the cypionate, I expect little difference in function.

Step 1: 1-Test cyp is reacted with tetramethyl dilithium pentacuprate (formed in-situ from CuI and meLi). The reaction is quenched with liquid bromine. The product is 2-bromo-1-methyl-DHT.

Step 2: The bromine is eliminated to give back the 1,2-double bond by stirring with DBU as in the synthesis of bold cyp. The product is methenolone cypionate.

MESTEROLONE (proviron)

1-Test base is reacted with tetramethyl dilithium pentacuprate (formed in-situ from CuI and meLi). The reaction is quenched with water to afford mesterolone in a single step.

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.

B]

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

 

[balls]

Goos stuff spidey.
Can you post the references for those? I'm especially interested in MnO2 oxidation of the diol to give boldenone.
Another conversion you can add to the list is methyl grignard addition to DHEA to yield methandriol (even though people don't like it). One step procedures from over the counter stuff are apealing!
Also, in the case of DHEA (and I suspect testosterone analogues), addition to the carbonyl always occurs from the alpha face due to the adjacent methyl group which is beta.
So you don't have to worry about mixtures of products.

 

[Sigmund Roid]

Did you actually use your nandrolone? How did you assess its purity? Better yet, how did you purify it?

Andy

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.

 

[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

 

[CIL-BAHA]

Hello Andy & Spidey & Chem_kid & Roomies!
I want to change Boldenone to one that is volatile to be detected by GC-ECD, using trichloroacetic acid, and the usually available lab acids.
Do you know a pathway I could utilize?
Thanks

 

[bremac]

I know this is incredibly old thread but since I landed here I'm sure others will too. there seems to be a lot of confusion and discussion with regards to steriochemistry. Commercially, the 17 one group of androdione is reduced with lithium aluminum hydride or sodium metal in ethanol to afford androdiol which in turn is 3-OH oxidized with manganese dioxide. Alternatively you can reduce with sodium borohydride that is about 80% selective to the 17 OH over the 3. This leaves about 70-80% test base and 20-30% androdiol or unreacted androdione. Commercial syntheses don't make it to the floor if they are not efficient, the structure of the feedstocks of the molecules dictate the correct steriochemistry and the reagents the selectivity. For example some ask about test from DHEA, reduce with one of lithium aluminum hydride, sodium or sodium borohydride and upon oxidation of the 3-OH it will rearrange the double bond to 4 if the correct pH is maintained. If selenium dioxide is used to oxidize the 5 ene will rearrange to the diene as seen in methandieneone or boldenone.
The best way for prep of these is to let microorganisms do the work. Pretty much any yeast will do a good job but there are some that are very specific (names elude me). From DHEA thru to test with 100% selectivity with just feedstock and yeast nutrient. Same with androstenedione. The best way to test from androdione is a cold overnight stir with borohydride, it will leave most of the 3one alone.
When it comes to impurities what you need to understand people is that the gov't and the educational system plant into your mind the idea of if something is made outside the taxed pharma industry it will contain deadly poisons and chemical warfare agents will result from a reduction of dhea. Not the case, if you are careful and use the right materials you will get unreacted feedstock, desired product and then over reacted or improperly reacted which usually means it will lose the same"macro characteristics" of the feedstock like solubility and therefore a fractional recryst. will purify plenty. When it comes to injecting there is nothing magic either, you must remove pathogens (germs) and pyrogens (cause inflammation), so, filter thru .22micro filter.......done. Or boil and centrifuge, pipet off the top.........done.......sterile. Filter at .5 micron and add 5% benzyl alc. nothing will live. Remember the old steroid pharma preps where 5% BA in sesame usually. None of the 6 componant concoction crap is need, that is just to try to cram 40kg/ml into solution for these guys who abused test to the tune of a gram a day for ten years. Keep your shit to 50-100mg/ml and 5% ba in oil with a decent pyrogen filter out and you are good, a little BB cuts back on discomfort but you won't get dyptheria, herpes or St. Vitus dance, if you don't put it in

 

[Ron_Mexico]

Very nice work bremac

 

[redsamurai]

did the andro powders ever become completely illegal?