Acacia confusa

[Tomer Corymbosa]

Root bark of this species was found to contain some %2.58 total alakloid, of which %55.25 was reported as N-methyltryptamine, and %44.75 reported as N,N-dimethyltryptamine. Notes that it has a history of use in Traditional Chinese Medicine for fever, inflammation and for diseases of the blood. Currently the highest specific record of N,N-dimethyltryptamine content from any plant material published ever.

a friend send me this info form website.

http://mulga.yage.net/acacia/

do u think a.confusa is the most potent spp??? i dont think its true...

[Torsten]

I am growing confusa and will have material for TLC analysis next year (and hopefully seeds a couple years later). I don't see why it would not be the most potent species, although its real magic would be in finding an OTC method of putting an extra methylgroup on all that NMT.

Come to think of it, how about something as simple as formaldehyde and aluminium amalgam?

[teonanacatl]

would Eschweiler-Clarke reaction not work? The amalgum could work (just a clemmensen reduction on an imine which ive never heard of), clemmensen reduction requires some pretty acidic conditions i believe so if the Eschweiler-Clarke wont work then the clemmensen wont work. Apparently the ideal pH for imine formation is 4-6 but i would assume it depends on the pKa of the nitrogen and i wouldnt go less then 1-1.5 pH units below pKa. Can use toluenesulphonic acid with good results.

[Torsten]

I am always amazed at how divergent chemical synthesis theory is from practical work. There was quite a bit of work done on tryptamines on the hive and the concensus was that anything acidic was useless and would result only in tar. The aluminium amalgam method (which is an alkaline process, so probably not what you had in mind) was tried by a few people and also failed.

Only one reducing agent did an acceptable job, but it is a highly watched chemical as it was Strike's "Blue Ribbon Favourite" for one of his amphetamine methods. Not saying there isn't a way to achieve this, but it's a bit of a waste of time covering the same processes again and again. I hope someone comes up with something new.

[Torsten]

Eschweiler-Clarke clarke is a variant of leuckart, so it would probably require heat (the only way to get the CO2 evolution which drives the reaction), so that's definitely not going to work.

Clemmensen is the zink reduction which had been tried and posted about on the hive. It is so acidic that it will fail before it even starts.

I think one of the most promising reductions would probably be a Pd catalyst reduction using H2. Although I am not sure if this will have the same problem as the hydrides which will reduce the formadehyde preferentially to the imine.

[teonanacatl]

Of course its different its just the theory needed to come up with a desired compound :D, one comes up with several synthetic schemes then works about getting them to happen (the practical component), and just because somthing doesnt work you dont stop you modify it abit and see if it works. Thats how they could have found that acid and tryptophan result in autooxidation, theory wouldnt tell them that but the theory derived from the practice may shed light on a mechanism by which such a reaction takes place, it goes from being a problem in one case to a new technique in the organic chemists arsenal :D

Most of the clandestine chemists ive talked to lack the theory but can tell you 5 practical ways to do step x--->z but yeah they dont know how it works and what everything is for, whereas at university in you undergraduate course you learn very little about practical stuff in synthesis, you learn practical techniques such as recrystallisation and distillation plus more and do pracs which show you some processes. But you dont design and synthesis compounds, this comes later. Then once youve gained experience your really above both in knowledge and practicality. Though i dont doubt that some clandestine chemists are trained chemists with years of experience.

Say I want this chemical conversion done, I can tell you all the ways in theory I know you can do it, I then research them and find out if they will work, i havent researched them yet so have no idea why acidic environment is so bad or heat for that matter. When i find out perhaps I will be able to offer some useful advise :D I will have a look for what they did at the hive also.

Edited to say:

I actually think that the theory does provide alot about how the reaction is carried out, if we use imine synthesis as an example we require an amine and a carbonyl, the amine must be nuclephilic, nucleophilic attack by the amine gives a tetrahedral intermediate which is protonated and looses water. From that lots about a reaction can be infered. The reaction will be carried out in anhydrous conditions and the water removed to pull the reaction to the products, so do it in toluene and you can azeotrope off the water. Next bit is it requires an acid but not too acidic conditions that the amine is protonated and non nucleophilic, so use toluenesulphonic acid and add it a bit at a time. If you look up a imine synthesis that is what you will find, so whilst i do agree that it is somewhat cut off from the practical side what in my last post made you say that?

Edited October 30, 2006 by teonanacatl

[teonanacatl]

Ok so i searched for tryptamine stability in acidic solutions and found no mention of degradation. Actually found its used to add chromophores to reducing sugars, infact formation of imines with tryptamine is quite prevalent in synthesis such as that of b-carbolines via the Pictet–Spengler reactions, as is tryptophan.

No search results were found regarding N-methyltryptamines stability or reactivity, which is what this thread is about, obviously tryptophan, tryptamine, N-methyltryptamine and DMT are different chemicals and just because one degrades easily doesnt mean the other will.

I didnt look to hard and only used google, when I get a chance sometime Ill search the uni database.

I also looked for a link to anything said at the hive but couldnt find one, nor a link to their archives.

Found a pile of references to tryptophan -> tryptamine at the rhodium archive (are these all crap?) Including one which I had wondered about and thats using a heavy metal catalyst in decarboxylation, they mention

[Qhorakuna tantani]

The tryptophan to tryptamine using carvone seems like a fairly usable reaction too as long as it works... apparently it works with substituted tryptophan aswell... is Dimethyl-tryptophan available?

[Auxin]

is Dimethyl-tryptophan available?

Its in a few plants- if I remember right N-methyltryptophan (common name 'abrine', Not!! abrin) is in Abrus precatorius (sp?) with smaller amounts of N,N-dimethyltryptophan noted.

The major alkaloid of Pultenaea altissima is N,N-dimethyltryptophan methyl ester.

Aotus subglauca is N-methyltryptophan methyl ester dominant with some N,N-dimethyltryptophan methyl ester.

Gastrolobium callistachys has (S)-(+)-Nb-Methyltryptophan [(+)-abrine](1),(S)-(+)-Nb-methyltryptophan methyl ester(2),(S)-(+)-Nb,Nb-dimethyltryptophan methyl ester (3) and methyl (S)-(+)-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

Other plants have em too.

...so ya these things are around

[MarsOfOld]

The most important thing is not the DMT concentration. The most important thing IS the alkaloid profile. Even if this plant has 2.58% alkaloid, if only 45% of that alkaloid is DMT, then after the extraction what you've got is weak DMT. Under 50% pure. Unless you're gonna use chromatography or a bulk method of zone electrophoresis, you won't be able to concentrate the DMT beyond 45%. Better to have some other plant like Psychotria Viridis/Carth or Acacia Obtusifolia which have better alkaloid profiles. Low concentration can be overcome with the generous use of solvents, but a low alkaloid profile is much tougher to overcome to end up with a high percentage of DMT in the final product. Hypothetically speaking, of course...

[Auxin]

Unless you're gonna use chromatography or a bulk method of zone electrophoresis, you won't be able to concentrate the DMT beyond 45%.

chromatography? electrophoresis!!?!! you sure do like doing things the hard way

The rest was NMT which is quite easy to remove from DMT

[Qhorakuna tantani]

Is it possible and practical to use an enzyme to methylate the rest? Such as tryptamine N-methyltransferase, which methylates NMT and tryptamine, whether or not its commonly available is the question or whether there is another more commonly available enzyme that will have the same effect.

[MarsOfOld]

I'm all ears. How would you separate the NMT from the DMT? Using a solvent to selectively separate them? If so, which one dissolves the one, but not the other?

chromatography? electrophoresis!!?!! you sure do like doing things the hard way

The rest was NMT which is quite easy to remove from DMT

[teonanacatl]

NMT has a N-H bond which DMT doesnt have thus can act as a hydrogen bond donor, thus recrystallisation from a somwhat polar solvent would THEORETICALLY work, ie acetone. Even recrystallisation from hexane may purify it. If you have access to acetic anhydride then that will react with NMT to give an amide which is non basic and so can be separated. A friend of mine told me about a dream where he ran TLC on some DMT extracted from acacia and only got two spots, one corresponds to the oxidation product and the other to DMT, whether the DMT and NMT didnt separate I dont know though that shouldnt be hard to work out.