Sciencemadness Discussion Board

Ideas for OC synthesis with OTC starting materials

RogueRose - 6-3-2017 at 15:23

Disclaimer, I have very little experience or knowledge in OC so please forgive me if my suggestions are ignorant.

There was a recent thread asking people what they would synthesize if starting out in OC. While I'm new at this I was thinking of of some things and one that came to mind is various hormones, pro-hormones and other things closely related. There is a vast variety of supplements and "steroids" (not all illegal, especially in more than 80% of the world, or 90% by population - and legal 100% medically) or even female hormones like estrogen and such. I think this would be very interesting to see how things like testosterone or estrogen can be made from cholesterol or DHEA. There are so many different "steroids" based on testosterone (38 last time I counted, not including esters) each with the slightest differences which would be very interesting to see how those differences are "created"/synthesized.

Another interesting idea would be using Caffeine and Nicotine as building blocks for whatever can be made of them. They seem to be somewhat similar in structure from a novices POV and they can be easily obtained in pure forms as either a powder or in concentrated solutions (glycerine or PG as the solvent/carrier for nicotine).

What do those with experience with OC have to say about this?

I'm also interested in doing extractions (and manipulations - down the road) from things which I can grow/forage but would like some suggestions as to what would be good suggestions to start this endeavour (planting season is coming up fast, so I'm all ears!)

Here is a synthesis chart for male/female hormones

PirateDocBrown - 6-3-2017 at 15:41

This is not really an OC synthesis. This is biochem. Note all catalytic factors are enzyme proteins. Sure, it can be done, but this is bio lab stuff, not chem lab.

Lillica - 6-3-2017 at 15:50

I've looked into the steroid route before out of curiosity. Going from DHEA to the various Testosterone derivatives just too easy. Last time I looked into it, I recall it just being a few simple oxidations/hydrogenations, that were completely quantitative with minimal workup. Hardly a challenge by any measure, and with no new carbon bonds being formed.

Though just be careful if you're in the US... pretty much all notable testosterone derivatives you can think of are going to be illegal under the Federal Analogue act. They might be medically legal sure.... but cocaine, amphetamine, methamphetamine, and opiates are also 100% medically legal ;p.

I personally say go for something involving at least 1 carbon bond forming reaction... in my opinion that's the most fun and relevant part of organic chemistry.
Quote: Originally posted by PirateDocBrown  
This is not really an OC synthesis. This is biochem. Note all catalytic factors are enzyme proteins. Sure, it can be done, but this is bio lab stuff, not chem lab.


I think he was just using the picture to demonstrate how related the molecules are in their synthetic pathways.

[Edited on 6-3-2017 by Lillica]

clearly_not_atara - 6-3-2017 at 16:18

This topic comes up all the time:

https://www.sciencemadness.org/whisper/viewthread.php?tid=67...
https://www.sciencemadness.org/whisper/viewthread.php?tid=65...
https://www.sciencemadness.org/whisper/viewthread.php?tid=67...

Without knowing a whole lot about your skill level I suggest your first synthesis target should be butyl isonitrile.

JJay - 6-3-2017 at 16:41

It looks extremely hard to make androgens from DHEA without 3B-HSD. Then again, maybe someone knows how, but I am out of ideas... also, the cholesterol sidechain is not an easy side chain to cleave, is it?

Dr.Bob - 6-3-2017 at 17:36

A few of those transformations are easy, most are not, and steroids are among the hardest compounds to work with in OC, as they are mostly not UV active, so hard to detect via UV.

There are some huge books dedicated to steroid chemistry, most are pretty dense. I would skip them for a while (forever for me, having worked on them), and go towards simple chemistry like esters, amides, and aromatics. If you want to try to isolate cholesterol from gallstones, that is doable and a common organic type lab experiment. But if you want to make estrogen, go for it.

j_sum1 - 6-3-2017 at 17:44

I think making a series of esters is interesting and will build your skill level.
Then you might try some extractions and see where you can go from those extracted compounds. chemplayer has a great series starting with white pepper and leading to all kinds of interesting compounds. (Watching all of his videos systematically in order is highly highly recommended.)
You might also have some kind of target molecule and work out a pathway to synthesise that. Phenolphthalein is a classic as is luminol. But you could go for any dye or indicator (within reason.) NileRed takes this approach and has several series that he does on this.

If that does not give you enough interesting ideas then you just aren't trying. :)

RogueRose - 6-3-2017 at 19:50

Thanks for moving the thread. As I said I am a OC neophyte so I wasn't sure how it would be classified. I posted that graphic simply to show the relationship between the various compounds and how they can be transformed from one to another.

As far as why I suggested these, I was absolutely amazed when I had access to a pharmacies script filling and prices for some of these compounds (testosterone basically). One month of a gel that was rubbed into the skin (daily) ranged from $800-1500 per month and they filled 60-80 per month! The other was the injectable 10ml @ 200mg (2g total) at $175-300 per vial and they filled 240-300 per month! That seemed to show there were quite a few people who used these at that time though I don't know if this was for one location or for all branches of the pharmacy.

In many countries it is totally legal to synthesize these compounds and from what I have read and heard, if leagally prescribed, a legitimate prescription holder may make/synthesize their own medications even if they are "listed" or scheduled. I'd like to know if that is in fact true or if it is Internet gossip. I did read some statues on the FDA and DEA sites which seemed to support this as they supported this for medically accepted "drugs" with a legal prescription.

In addition to the "scheduled" drugs, there are a vast number of "steroid like supplements" which are derived from compounds chemically close to testosterone. I'm not up on the supplement market anymore but I'm sure there are some compounds sold at GNC which are derivatives (not sure correct word) of testosterone.

As far as the mention of nicotine and caffine IDK if there are interesting compounds which could be made with those as starting blocks.

I'm also interested if Yohimbine (or the HCl of Yohimbine) could be interesting for anything as a starting point.

I'd really like to learn more about OC but it seems pretty intimidating IMHO. I tend to look at the structure of the molecule and then see what other molecules are similar and see if one can be made into the other. IDK if this is a naïve viewpoint or what a better way is of looking at these things, but it is how I started learning how some aspects of chemistry works.

JJay - 6-3-2017 at 20:03

I recently ordered a book titled Systematic Organic Chemistry, which covers mainly aromatics. It's kind of like a cross between an introductory organic text and a lab manual and looks quite easy to read for small-brained individuals such as myself :)

JJay - 6-3-2017 at 20:18

Quote: Originally posted by j_sum1  
I think making a series of esters is interesting and will build your skill level.
Then you might try some extractions and see where you can go from those extracted compounds. chemplayer has a great series starting with white pepper and leading to all kinds of interesting compounds. (Watching all of his videos systematically in order is highly highly recommended.)
You might also have some kind of target molecule and work out a pathway to synthesise that. Phenolphthalein is a classic as is luminol. But you could go for any dye or indicator (within reason.) NileRed takes this approach and has several series that he does on this.

If that does not give you enough interesting ideas then you just aren't trying. :)


Oh yeah... Chem Player's synthesis of heliotropin from pepper... that involved breaking a carbon chain at a benzylic position. Manganese-based oxidizers selectively break carbon chains at benzylic and allylic carbons, or so I have read. Even that oxidation was apparently not trivial.

j_sum1 - 6-3-2017 at 21:38

Not sure if you are being sarcastic or not Jjay.
My point, if it wa not clear, was to suggest an approach where you isolate a compound and see what can be done with it. I was not necessarily endorsing a duplication of chemplayer's work beginning with white pepper.

NileRed and Nurdrage have had a different approach where they have a target compound.

For someone beginning OC, having some kind of goal seems a good idea: which was my main point.
My second point was to direct the OP to some nice clear examples of what can be done. Not knowing RR's skill set, ambitions, interests and equipment, it is hard to be too specific. But I know that watching procedures breeds ideas -- which seemed to me to be the main question here.

JJay - 6-3-2017 at 22:26

I'm aware of a few things that could be done with it. I must admit that I am slightly curious - from Chem Player's description, it sounds like the substance would make an excellent flavoring for cakes and pies. What could possibly be more decadent than a bowl of piperonal-flavored homemade ice cream.... I'm not quite curious enough to actually make some piperonal (seriously), but I completely respect the chemistry there, and I know a lot of people are extremely interested in producing some. I'm just not.

My point was that breaking carbon side-chains is generally not easy. It can require exotic catalysts and uncommon oxidizers. But that's far from being the biggest problem with steroid chemistry--don't forget all those chiral centers that are easily epimerized..

I'm not really sure what RR's skills and knowledge are either, but it seems like his heart is in the right place.

My current target molecule is benzoquinone, using acetaminophen as a starting material. This is thought to be fairly easy, but it's hard to find a reliable report where someone has actually done it, probably because it is easy to buy benzoquinone.



[Edited on 7-3-2017 by JJay]

Texium - 7-3-2017 at 07:04

Quote: Originally posted by JJay  
I'm aware of a few things that could be done with it. I must admit that I am slightly curious - from Chem Player's description, it sounds like the substance would make an excellent flavoring for cakes and pies. What could possibly be more decadent than a bowl of piperonal-flavored homemade ice cream.... I'm not quite curious enough to actually make some piperonal (seriously), but I completely respect the chemistry there, and I know a lot of people are extremely interested in producing some. I'm just not.
We have a bottle of piperonal in the lab that I work in and it does indeed smell delicious. Like a mix of vanilla, almond, and cherry. It would be very good in ice cream, albeit probably not by itself.

Melgar - 9-3-2017 at 04:46

I got piperonal from black pepper essential oil via ozonolysis once; it smelled like maraschino cherries. Organic syntheses that clearly change color and smell at important points are often some of the best for beginners, since they can perform them without knowing how to do TLC, and then appreciate the need for TLC when it comes time to learn that skill.

anewsoul - 9-3-2017 at 05:04

I'd suggest starting with simpler projects like chemplayer's piperonal. I did that over the winter and it's really fun, can be a little frustrating, but you learn a lot. Just try to find simpler easy to obtain molecules like that and study them, see what you can do with it.