-
Members of the previous forum can retrieve their temporary password here, (login and check your PM).
DMT-n-oxide Molecular Structure?
- Thread starter romiir
- Start date
I see, that answers one of swim's questions... I was kind of hoping the oxygen was in a different spot, I highly doubted it to be in position 4... Now swim's question is, has anyone ever figured out a way to make this molecule from DMT?:
edit: First time posting a pic on this forum, ack that looks ugly, need to use white on transparent I guess... Will fix this in a second.
O-benzyl-N.N-dimethyltryptamine:
edit: First time posting a pic on this forum, ack that looks ugly, need to use white on transparent I guess... Will fix this in a second.
O-benzyl-N.N-dimethyltryptamine:
It'd be easier to make it from psilocin. Psilocin is 4-oh-DMT. Then you could, in theory, use benzoic anhydride to make 4-benzoyloxy-DMT and then reduce the benzoyl to a benzyl, but I don't see why you would want to, since the ester would surely be more active.
Hehe, you see where SWIM is going.... and that is good advise if it were the target molecule.. However SWIM was wondering if there is a way to attach 4-oh to DMT... I was thinking along the lines of a prodrug to psilocin which is easier to produce once this reaction is figured out, no waiting on the mushrooms...
See:
See:
They like to get all contaminated and have poor yield. If SWIM could do this TEK, it would result in mimosacybin! In nice quantities I might add... (even with the poor yield)
SWIM has access to some of the best spore prints possible for making psilocybin and psilocin, however the yield on that investment has been less then satisfactory. It's time to invent something better.
SWIM has access to some of the best spore prints possible for making psilocybin and psilocin, however the yield on that investment has been less then satisfactory. It's time to invent something better.
from 1 casing you get over 4 oz of shrooms.....and you can do like 10 casings at a time with minimal space and it takes ~2months..so just keep at it every week innoculating new jars....ive had 1 incident with contams...had 2 grow bags...1 was contammed threw it out..other one got me over an oz of dry...what exactly is this mimosacybin?
Have you ever heard "Practice makes perfect"?
As for yield, if you're talking about the amount of alkaloids per harvest, or in other words the potency of your mushrooms, look into cloning and strain isolation - the way to produce consistently superpotent mushrooms...
If you mean the amount of mushrooms, again practice makes perfect. Mycology is a fun hobby, once you get the hang of it. Don't let a few contaminations discourage you. You just need to pick a tek and follow it 100%, and pay very good attention to sterility.
Hint: grain spawn + bulk substrates is where the action is. I've had 500-600g yields from a single 2 liter bulk substrate tray. You can fit 4 of these substrate boxes into a 50l fruiting chamber. That's 2kg of fresh mushrooms per batch, which translates to 200g dried mushrooms, and cubensis can easily have 5mg per dry gram of psilocybin so you could get a gram of psilocybin per batch...
There is no known way to convert DMT into 4- or 5- hydroxy derivatives in any significant yields. I recall seeing something in a book years ago but the reaction was not selective and low yielding.
The picture of DMT N oxide is slightly incorrect too, the correct molecule has a single bond between the Nitrogen to the oxygen. The valency would not allow 5 bonds around the Nitrogen.
The picture of DMT N oxide is slightly incorrect too, the correct molecule has a single bond between the Nitrogen to the oxygen. The valency would not allow 5 bonds around the Nitrogen.
PerPLexED said:
I want to come up with a TEK to make 4-acetoxy-N,N-dimethyltryptamine. (Synthetic analog of psilocybin, theoretically possible to build from N,N-DMT...) This IS POSSIBLE, and HAS BEEN DONE. We just need to figure out the how. I have most of the details figured out, however I've yet to come up with a way to convert DMT into 4-benzoyloxy-N,N-dimethyltryptamine, which is then converted to 4-acetoxy-N,N-dimethyltryptamine in the synthesis I'm working on. Synthesis of 4-acetoxy-N,N-dimethyltryptamine from scratch is doable but is time consuming and we already have 90% of the molecule finished if we start with N,N,-DMT... The trick is getting an oxygen bond to the 4th position indole of the dmt molecule...
Even in low yields I believe this conversion would be a really neat thing to do. You can always run it through the chromatography column and separate out the good stuff.
However I don't think that would be necessary since the incorrect molecules would either die by monoamine oxidase or be inactive... or do something else cool..
I believe it would still be active to some extent even if it wasn't attached to the 4th indole of the ring, however I don't know a lot about pharmacokinetics of tryptamines.
Hmm... Long post, hope someone can read this and understand what I am trying to do. =)
Interesting too that Hoffman was the last guy to play with this, I greatly admire all of his work. See patent below.
Sources:
Patent - http://www.erowid.org/archive/rhodium/pdf/psilocin.esters.pdf
bufoman said:
Can you give me a link, a scan of the book, or even an ISBN, PLEASE!!! I would love to see these notes. Even on a low yield synthesis. We can try to improve it. Even with say, 10% yield, that means from 10 grams of dmt you can get at least 500mg of product after other reaction losses in a mathematically horrible model, yields are more than likely reasonable but lossy. It might even make some other fun molecules.
I wasn't able to find ANY information about the arrangement of DMT-n-oxide... So I have no idea, could someone draw the correct molecule for my reference?
The synthesis you are talking about starts with the substituted indoles NOT tryptamines.
The book is Psychedelic Chemistry by M Smith, I believe there is a synthesis for converting DMT into OH substituted analogues. However it was low yields if it even works. Not to be a pessimist but this is a VERY UNLIKELY REACTION.
It is not a good idea to just take a impure mixture of chemicals. Some could be toxic. Especially if using toxic reagents. Plus even with a column these compounds likely have very similar affinities for the gel as they are conformational isomers although they could likely be separated if done correctly.
Only tryptamines with Oxygens on the 4 and 5 position of the indole appear to be active as hallucinogens. Others have been looked at and found to be inactive. It is the pharmacodynamics that has to do with the interaction of the drug with the receptor. If the pharmacodynamic profile is bad the kinetics don't matter.
The book is Psychedelic Chemistry by M Smith, I believe there is a synthesis for converting DMT into OH substituted analogues. However it was low yields if it even works. Not to be a pessimist but this is a VERY UNLIKELY REACTION.
It is not a good idea to just take a impure mixture of chemicals. Some could be toxic. Especially if using toxic reagents. Plus even with a column these compounds likely have very similar affinities for the gel as they are conformational isomers although they could likely be separated if done correctly.
Only tryptamines with Oxygens on the 4 and 5 position of the indole appear to be active as hallucinogens. Others have been looked at and found to be inactive. It is the pharmacodynamics that has to do with the interaction of the drug with the receptor. If the pharmacodynamic profile is bad the kinetics don't matter.
David Nichols has published a way to make 4-ACOH-DMT starting from the substituted indole.
Also as I recalls the rxn by Smith uses strange and dangerous reagents as I recall and require a laboratory thus one is better off starting with the indole in theory if they wanted to make this compound.
Also as I recalls the rxn by Smith uses strange and dangerous reagents as I recall and require a laboratory thus one is better off starting with the indole in theory if they wanted to make this compound.
bufoman said:
Yes if I understand your last post, the yield was non-selective, but resulted in a slurry of both active 4 and 5 position indole hydroxy derivatives... and maby some other byproducts, but it can be purified [and perhaps recycled? (for the ones that don't react as expected..)].
This is a very unlikely reaction. Putting hydroxyl groups directly on benzene rings is VERY difficult in genereal.
I wouldn't say it is impossible but it will require a immense amount of starting compound to result in a small small amount of final product. Plus one requires a lab and difficult chemical reagents.
Recycling will be unlikely as most of the starting material will undergo one or another reaction. It is just that only a small bit undergoes the desirable reaction. The rest is lost as strange side products (tryptamine chemistry has many side products there are some interesting papers in forensic journals on these compounds).
I wouldn't say it is impossible but it will require a immense amount of starting compound to result in a small small amount of final product. Plus one requires a lab and difficult chemical reagents.
Recycling will be unlikely as most of the starting material will undergo one or another reaction. It is just that only a small bit undergoes the desirable reaction. The rest is lost as strange side products (tryptamine chemistry has many side products there are some interesting papers in forensic journals on these compounds).
Why not just start with psilocin. It should not be hard to acetylate psilocin. Or produce any other ester you may wish to produce.
Learning how to grow the mushrooms to acquire the psilocin would be 1000 times easier than trying to hydroxylate the DMT molecule.
Learning how to grow the mushrooms to acquire the psilocin would be 1000 times easier than trying to hydroxylate the DMT molecule.
Thank you everyone for the feedback, however does anyone have any example documentation I can read about attaching hydroxyl groups to benzene rings selectively? (4th and 5th position preferred)
Shouldn't there be a way to protect some of the molecule and get reasonable yields? (~20%?)
Assume SWIM has access to a complete lab with any necessary reagents.
Shouldn't there be a way to protect some of the molecule and get reasonable yields? (~20%?)
Assume SWIM has access to a complete lab with any necessary reagents.
