DMT n-oxide and zinc.

[DMTripper]

I just found some very old MHRB in my freezer and it yields very oily stuff.

I was thinking to boil the bark with acetic acid and throw a bit of elemental zinc powder into the aqueous solution and stir that up for a while before converting to freebase and pulling with hexane.

Shouldn't that give me whiter dryer DMT?

 

[endlessness]

Hey

If DMT was oxidized, then yes that should more likely give you white dry DMT. But it also might be that it simply is the way it solidified without propper crystallization. DMT is polymorphic and even pure DMT can be an oil.

If you were inclined to do experiments, you could also get half your yield do the zinc reduction and with half the group you do everything the same except not adding zinc, and then see what differences you have.

Good luck either way and do share results

 

[DMTripper]

Isn't this the right stuff?

 

[Jees]

Sounds like the real deal.

Oxides goto toluene very well, naphta not so unless really hot.
Doing the Zn in the wood stage is a cool idea to suit naphta well, looking forward for your attempt with adding Zn at the wood stage :thumb_up:

 

[DMTripper]

So I boiled the bark with a little vinegar and then it stood for probably two weeks while I was finding zinc powder and waiting for that to arrive. The bark did start to ferment in the bottles while I waited for the zinc so I couldn't boil it down to the volume I usually do because of a very foul smell that my wife was not too happy about in the house

I then used lye to basify and added the zinc powder to the solution and pulled with hexane.
And the outcome was pure white crystals
Quite happy with the results. Got exactly 1% yield, a little less then usual. But only did two pulls. And maybe the fermentation damaged something.

But I did an extraction on the same bark earlier and got only oily goo that was very hard to work with. I will definitely use this trick again
Going to do another soon and see the yield then.

 

[DMTripper]

Hmmm don't know why that photo turned upside down

 

[Jees]

...I then used lye to basify and added the zinc powder to the solution and pulled with hexane...

Do you have that order right? I suppose you added Zn first in the acid stage, let the Zn react with the acid. Then happens the n-oxide reduction. After that basing with lye and pulling.

Hmmm don't know why that photo turned upside down

For zero's that doesn't matter

 

[ijahdan]

Looks really simple and effective. Would it work for reducing harmaline to thh? For example, boiling syrian rue seeds in acidified water, adding zinc powder and then filtering, basing etc. rather than doing this with the extracted alkaloids. Obviously there would be a mixture of harmaline and harmine in the seeds but maybe some thh would form?

What about contamination by zinc salts that form? My understanding of chemistry is very rudimentary so might be misunderstanding the reaction.

 

[endlessness]

DMTripper, IF there was any DMT N-oxide, yes you would have whiter DMT with zinc.. But I dont think DMT in it's natural salt form is prone to oxidation.

If you do this experiment, please have a control group, or in other words, do a side by side extraction doing the exact same thing but not adding zinc. That way you can properly compare if something is indeed changing.

ijahdan, yes it works, here: Harmaline to THH reduction with zinc and vinegar works! (GC-MS results) - Plant Analysis and Substance Testing - Welcome to the DMT-Nexus

 

[pitubo]

For example, boiling syrian rue seeds in acidified water, adding zinc powder and then filtering, basing etc. rather than doing this with the extracted alkaloids.

You might be reducing any other component in the rue tea. Unless you know exactly what is in the solution, you won't know what is happening. It's called: "garbage in, garbage out". Always purify your starting reagents before attempting any reactions, especially if you are unfamiliar with the process.

Obviously there would be a mixture of harmaline and harmine in the seeds but maybe some thh would form?

What about contamination by zinc salts that form? My understanding of chemistry is very rudimentary so might be misunderstanding the reaction.

Salting with NaCl would leave the zinc in solution while precipitating the harmine and harmaline. The problem is that tetrahydroharmine is apparently hard to get to precipitate that way. But if you base it out, the zinc will also precipitate...

 

[endlessness]

oh im sorry I misunderstood the question...

Pitubo is right, you'd have a lot of reactions going on by mixing the zinc with pure rue tea, with unknown results.

If you already have harmala tea, its easy enough to do a simple base precipitation or salt precipitation (aka manske), and then filtering, redissolving the results and adding the zinc.

 

[pitubo]

I think that at least one salting with NaCl is a must. If only base precipitation is performed, the quinazoline alkaloids like vasicine are also precipitated.

A quick search got me these links that may provide more information about the reduction of the quinazolines:
http://pubs.acs.org/doi/abs/10.1021/jo5019415
155. The electrolytic reduction of vasicine
A polarographic investigation of the alkaloids of Peganum harmala - Chemistry of Natural Compounds
Alkaloids of Peganum harmala. Unusual reaction of peganine and vasicinone - Chemistry of Natural Compounds

 

[endlessness]

Im not sure TBH, if they precipitate when simply adding a base, because they are very water soluble molecules, it may be that even just base precipitating already separates most of them... But I think it'd be interesting to test it.. I just dont have time myself

 

[pitubo]

.. they are very water soluble molecules ..

Do you have references for that?

This site Vasicine-Synonym Peganine-obtained from the leaves of Adhatoda vasica claims "slightly soluble in water".

Maybe you meant the salt form is very soluble in water, just like harmine and harmaline?

But I think it'd be interesting to test it.. I just dont have time myself

I've strongly based rue tea, filtered and redissolved the precipitate, salted and filtered it (keep the harmala.HCl crystals apart), then based the filtrate and filtered it, then redissolved, salted and filtered that (yields a bit more harmala.HCl) and rebased the filtrate and filtered the precipitate. I get substantial amounts of material when I do that. Since I have not had it analysed, I cannot say if it is quinazolines, proteins or both. I don't believe there is much harmine or harmaline in it though.

 

[endlessness]

Hmmm, Im trying to remember where I got that info from.. Here it says vasicinone is soluble in water at 1.597g/l. You are right though that is more like 'slightly soluble' than 'very soluble', I stand corrected.. I seem to remember talking to benz about how that hydroxy group in the molecule would make it quite soluble in water.

Also now that I think about it Im pretty sure I did test the result of the precipitates from a spent harmala tea after having removed (supposedly) most harmalas during manske and the results were still mostly harmalas (seems not everything precips with manske). Its been years though, memory kinda foggy. I dont remember seeing vasicine/vasicinone in the results. If anyone is willing to do this test (do a manske precip, then do a base on the spent tea) and gather the samples, I can help getting it tested.


By the way pitubo you can do a preliminary test by at least trying to dissolve those precipitates in water and seeing if it shines under UV.

 

[Jees]

... If anyone is willing to do this test (do a manske precip, then do a base on the spent tea) and gather the samples, I can help getting it tested...

Too late it's gone, but it was like a slime almost

 

[endlessness]

lol


Here you go pitubo: Vasicinone, Vasicine and Deoxyvasicine - Collaborative Research Project - Welcome to the DMT-Nexus

 

[pitubo]

I seem to remember talking to benz about how that hydroxy group in the molecule would make it quite soluble in water.

Well it is only one hydroxyl group on an otherwise quite nonpolar molecule (when both amino groups are unprotonated).

Also now that I think about it Im pretty sure I did test the result of the precipitates from a spent harmala tea after having removed (supposedly) most harmalas during manske and the results were still mostly harmalas (seems not everything precips with manske).

Yeah, I remember reading that. That's why I did another salting and basing on the filtrate from the salting, to recover any bits of harmalas not salted out. I did the second salting on a smaller volume of solution, too.

I also used plenty of lye when basing the teas.

Its been years though, memory kinda foggy. I dont remember seeing vasicine/vasicinone in the results. If anyone is willing to do this test (do a manske precip, then do a base on the spent tea) and gather the samples, I can help getting it tested.

Scientific articles describing the analysis of rue seed contents report sizable amounts of quinazoline alkaloids present.

By the way pitubo you can do a preliminary test by at least trying to dissolve those precipitates in water and seeing if it shines under UV.

Since the presence of even minute amounts of harmalas will cause the fluorescence, I am not sure if this is a very useful test. Perhaps if I could establish a comparison with a progressive dilution sequences of it and a standardized solution, that might give some kind of estimate for the amount of harmalas still present.

Too late it's gone, but it was like a slime almost

I noticed that quality too. It is what makes me consider the possibility that the material contains non negligible amounts of proteins.

 

[pitubo]

Here you go pitubo: Vasicinone, Vasicine and Deoxyvasicine - Collaborative Research Project - Welcome to the DMT-Nexus

Tnx. I already read that thread earlier.

BTW, the psychedelic compounds page on the wiki has a bad reference. Vasicine has a link to vasicinone's page at PubChem.

I compared the two PubChem pages for vasicine and vasicinone, but they both list the same XlogP3, i.e. 0.4 . I find that a little puzzling, considering the extra ketone function on vasicinone.

 

[endlessness]

Yeah indeed its strange.. Prob a mistake ?

Im pretty sure I had gotten that xlogp info added to the wiki from the merck index, which I had also uploaded to the wiki but the link is broken now. I'll ask trav to recover it, or if anyone has access to the merck index please do post the info here.

Maybe the solubility isn't huge per-se, but enough to prevent it from precipitating.

Considering it was tested with two samples, one from me and one from snozz, and both showed that the 'spent tea' precipitates were mostly harmalas, I think that's already a good indication of what we are talking about. Would be interesting to test it with the precipitates after doing two saltings like you did though...


(talk about going offtopic, lol )