very cool stuff(ddnl)
- 01-08-2003, 12:09 AM
hey weiss, i'm glad your staying away from the stuff at this time. i am too for now, but have a lot of people asking me at school (alot of them juice, so when a friend asked me last summer i too started to research for a safer alternative). i think you are going about it the wrong way. i know that one can do all sorts of calculations (i've taken alot of organic and physical chem during my biochem degree) but all those figures already exist. i will try to hunt them down tomorrow. unfortunately the reaction is not promising because other compounds are formed one is a pregnelone. as for acetic acid get glacial, its like 99%. if you live in a large city you could get it from a chemical supply company. as for weiss, you could probably get it at school (join the science club and do an experiment preferably one that requires lots of acetic acid, then make sure alot more is ordered and borrow some).
enthalpy is the bond energies of the bonds in question, entropy is not a factor since the two positions would have the same process take place. the only reason we have to worry about enthalpy is that if we use too strong an oxidizing agent, then both OHs will become ketones (we would be making androstenedione). the testosterone molecule however, is not aromatic, it only has one double bond. when it aromatizes it becomes an estrogen in which the A ring is aromatic. as for the strength of the bonds between C and O i believe that the 17 position is stronger, here's why: even though the ring at 17 has only 5Cs, it is adjacent to a quatrenary carbon which is very stable, also the adjacent carbon to C3 has a double bond which actually helps to destabilze the C-O bond and when C=O forms it will then be able to form a resonance with the double bond (though not to the degree of an aromatic ring).
just trust me for now, i will get the data as soon as possible and if i'm wrong i'll tell. as for going through complicated math, don't bother, there is an easier way i'm sure. i will try to post all the thermodynamic data so we can all be on the same page. i will also keep looking through the synthesis manuals i'm sure the reaction will probably be there too.
weiss talk to me before you do any long calculations, i can probably find the data in the critical tables which will be better than an approximation. also the reaction will not require extreme conditions, it will be in room temp in water (all good process chemists try to make all reactions such - i am not a process chemist). by the way weiss you were on the right track except for the bond strengths, good work, for a young'un your pretty sharp.
BTW this process will work for 19nor4androstenediol --> nandrolone
- 01-08-2003, 02:18 PM
if anyone is doing research don't just look under androstene derivatives, but also under hydroxyketosteroids and ketosteroids, many old synthesis text use these nomenclatures.
- 01-08-2003, 05:46 PM
Nice info Pete.
I don't know much about organic chem and have only read a few books on the subject, never any fomral studies. By aromatic I ment heterocyclic(i think thats right). I believe you with the stability of the bonds in the the two positions and I am guessing the 3 should have a better conversion rate. But I still think knowing the mathmatics would be important. From my understanding test, diols, and diones should all differ in their entropy due to the relative location and how this effects compound stability. With entropy and enthalpy we could work out the equilibrium rates and see to what extent this occurs and how temps plays an effect.
In theory diol with a an oxidizer like the dichromate ion and a decent acid would convert the hormone and we would get various products but it would be nice to know the degree these products occur. We won't want just a full yeild of diones do to conditions.
About the acid, personally I could aquire alomst any chem I needed but since this isn't for me I wanted to develope a procedure that the average Joe can perform. I fiquired by finding a non-volitile chemical that could easily be distributed through the main that would bond with acetate ions into a non soluble product would create a decent strength acid from vinegar. This would be much more conviniet than everyone trying to aquire some quality sulfiric acid or such.
Like I said its not like organic chemistry is my specialty and if I am off track let me know, I know I still have a good deal to learn in that area.
01-09-2003, 11:34 AM
what i meant by not doing loads of math is that it is useless to use models to calculate the bond enthalpies of the 3OH and 17OH as these are available. we still have to do some simple calculations to find which oxidizing agent is effective for our needs (oxidize at C3 but not at C17). while it is true that most reactions could be pushed at higher temps to occur, it is harder to control them (yeilds, etc.). most alcohols will react easily at room temp we just need the right oxidizing agent. remember PA said that it was simple. i am also looking for a simple reaction, not so much for an easy set up, but for efficiency both pricewise and yeildwise.
01-09-2003, 10:47 PM
crazypete and weismuller are both genuises and i give them props for working this stuff out. i wish i could help out more, but this stuff is way beyond me. just reading this stuff blows my mind.
once you get all the kinks worked out, i definitely want to try this. just tell me what to mix with what and how much and i'll be good to go
thanks guys, keep up the mad scientist work!
01-10-2003, 03:05 AM
I'M CRAZY NOT MAD. GET THAT STRAIGHT.
just kidding. unfortunately i have had a hard time with the reference texts. they were not comprehensive as i had hoped, but my earlier hypothesis about the bond strengths are correct, however, i still have no numbers. don't ask, i was in the library all day.
too bad kilosports doesn't sell 5AD, that conversion is jokes and 100% yeild.
anyway we will find the reaction. it will be simple. i'm also working on a 4hydroxyandrostenedione from androstenedione. it looks simple, but i have to go back since originally i didn't write down were i saw it, but i saw it more than once, so it looks promising. 6-OXO and 1,4dione may also be possible although maybe not economical.
thanks for the compliments pogue, but what should blow your mind is that some real geniuses figured this stuff out like 50-70 years ago and it was old news by the time anyone thought of cheap anabolics or even about anabolics. i'm also blown away by weiss' breadth of chemical knowledge and ability to grasp key concepts (weiss are you really 16?). he has a future as a chemist.
01-10-2003, 01:40 PM
5-ad is very very easy to get..im actually usaing it right now and love the ****(pentabol extreme)..if u could throw down that conversion that would be great man..i appreciate all ur hard work
01-14-2003, 08:58 PM
Okay Pete today I actually did a very simple set of calculations for the therms of this reaction. The good new is as expected Diol to Test is very product favored, to slight degree more so than the oxidation of the other OH yeilding a ketosteroid(I forget the name). Unfortunatley the oxidation of Test to Dione is slightly more product favored than Test to Diol. This yeilds me to believe with excess oxidizing agent at standard conditions we'd get a yeild of mainly Dione.
I must emphasize(sp) that these conversions were quick and simplified. I neglected the ringed adjustments and will try to redo these calulations sometimes soon. I am working with partial understanding of this system(something I hate to do) but I don't have Benson's book nor are the resources availible over the net. But I'll keep working and should be able get the necessary values once I improve my understanding of how cyclic fits in.
I am not sure how much this will effect the values and if it'll improve relative favorness and such, but I am preparing for the worst, meaning the proccedure will need be designed with this in mind.
The one good thing that I can think of is that no matter what the results will be a mix. Since diones and diols use different enzymes if we can get their percent comps low enough the majority of these non test products will be converted to test in the live and with the addition of the test created by this procedure almost everything will become test. Of course if this is 99% dione yeild then it won't mean jack. I'll keep looking in and try to aquire Benson's book through my school or public library but that would probally take while.
By the way I am 16 and junior is HS. I only have 2 years of formal chem ed under my belt but this stuff is one thing I really understand and have an interest in and have been teaching myself other parts of chem outside of school. Hope to one day be doing something in chem.
01-15-2003, 09:49 AM
yeah its true that if there is too much oxidizing agent then it will convert the 17OH to a ketone, but we can put in another alcohol with a bond strength in between 3OH and 17OH to take care of the excess oxidant and still get complete test formation. don't worry, we'll get this thing dead on, i have a few more tricks up my sleeve.
i haven't been to the library in a few days, kind of busy, but will get to it.
01-20-2003, 03:41 PM
hey guys, i found a good book:
ORGANIC REACTIONS IN STEROID CHEMISTRY
Fried & Edwards, 1972
active platinum catalyst, inert solvent e.g., acetone or ethyl acetate
- selective dehydrogenation of 3-hydroxyl group in ?4 polyhydroxysteriods without attacking double bond or 17OH
-yield is 75% but procedure is not easy, like you could screw up easily in a proper lab
i will look into using a simple protecting group on the 17OH.
01-20-2003, 04:42 PM
the answer is MnO2 manganese dioxide (p.244-247 of the book in above post).
more to come, i think we got it.
01-21-2003, 10:57 PM
I think we should continue with the procedure on a new thread. Not trying to step on anyones toes or anything.