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Manske seems to precipitate another rue alkaloid under certain conditions Options
 
Jagube
#1 Posted : 12/5/2019 11:32:52 AM

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I used to do a double manske, i.e. after the first precipitation I'd collect the supernatant, reduce it and do a manske on that. And my end products would sometimes have an unpleasant effect I couldn't put my finger on. Initially I thought it was harmaline, but later on I realized harmaline doesn't feel like that.

My harmine - dhh separation attempts, followed by a zinc reduction on the dhh fraction, would result in the unpleasant effect being felt in both the harmine and thh fractions and I erroneously thought it was because both were contaminated with harmaline.

I'm glad to have discovered this, because now I know the effects of harmaline as not as unpleasant as I used to believe; it's something else.

In my last extract I only did a single manske and that effect is not present.

It seems that in the first manske (on a crude rue extract), harmine and harmaline precipitate preferentially, but once those have been removed and the solution gets concentrated enough that the concentration of the unpleasant alkaloid exceeds a certain threshold, that alkaloid, too, will precipitate.

The subjective unpleasant effect of the alkaloid in question is what I call lightheadedness, for lack of a better term. It's a cold, lightheaded sensation in my head that comes and goes in an irregular manner. Like a cold knife blade being put to my brain.
 

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Loveall
#2 Posted : 12/5/2019 6:42:38 PM

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You are also increasing the salt concentration. Different things precipitate at different salt concentrations. What is your salt % for the 1st and second manske you are doing?
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Jagube
#3 Posted : 12/5/2019 6:54:52 PM

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Loveall wrote:
You are also increasing the salt concentration. Different things precipitate at different salt concentrations. What is your salt % for the 1st and second manske you are doing?

For the 1st it's 15%. For the 2nd it's hard to estimate, because I don't know how much salt remains in the post-1st-manske supernatant. And I was never consistent with the 2nd manske in terms of how much I reduced the volume and how much (if any) extra salt I added.
 
coAsTal
#4 Posted : 12/5/2019 8:45:42 PM

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Can you better explain what you mean by "unpleasant effect"?

 
Jagube
#5 Posted : 12/6/2019 10:06:59 AM

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coAsTal wrote:
Can you better explain what you mean by "unpleasant effect"?

Not really I'm afraid, it's hard to explain a physical sensation like that as there is nothing to compare it to. I also experience it with plain rue seeds or tea, but not with mansked harmalas.
The effect comes on a bit later than harmine. But I haven't heard of anyone else reporting this, so maybe my seeds contain more of this alkaloid or it's my sensitivity to it.
 
Jees
#6 Posted : 12/6/2019 11:49:35 AM

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An interesting (yet subjective as always) observation.
I'll try to re-manske liquids as you did in later experiments.

Jagube wrote:
...In my last extract I only did a single manske and that effect is not present...
Just to make sure: same batch of seeds?


 
Loveall
#7 Posted : 12/6/2019 7:05:44 PM

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Looking at it from the "other side", has anyone ever done a "pre-manske", say at 6% salt or so.

So whatever crashes at 6% may mostly be non-harmala stuff. If you remove that, then when you move to 12% salt and crash again you may have cleaner product. Just a thought, I imagine this has been tried before anyway but can't find the info.
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Jagube
#8 Posted : 2/26/2020 10:26:29 PM

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Jees wrote:
Jagube wrote:
...In my last extract I only did a single manske and that effect is not present...
Just to make sure: same batch of seeds?

Yes, same batch.

I've done more extractions and they seem to confirm that when the concentration of something (either NaCl or alkaloids, but most likely NaCl) is above a certain threshold, it precipitates an alkaloid other than harmine and harmaline that has unpleasant effects.

My last manske had 13% NaCl and the resulting product is devoid of the undesirable effects.
My previous one had 18% NaCl and I still only did one cycle; the undesirable effects were present.

This alkaloid seems to have a pKa closer to that of harmine as it tends to, for the most part, co-precipitate with harmine in harmine/harmaline separation attempts.
 
Jees
#9 Posted : 2/27/2020 7:22:52 PM

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In my limited experience, how well something precipitates under manske is not only salt concentration dependent but also alks concentrated dependent. Do you follow a certain habit which alk concentrations you work with?

The times I re-based a manske filtrate liquid it yielded a non catchable slime. I did not concentrate the liquid. Next time I will concentrate before 2ndmanske.


Sometimes this baffles me:
- make a raw tea from seeds, ph like 3, let settle for 24hours;
- decant & make sure no solids come along, dispose solids;
- base the liquid (I goto 12), settle for 24 hours, decant & dispose base liquid;
- add water to solids, now bring solids back into a solution of ph 3

now I get a ton of stuff that stays solid, shaking, time, nothing helps.
Why is this foul looking grey stuff now at ph 3 refusing to go in solution, while it was surely in solution in the raw seed tea at same ph 3, in same sorts of concentration?
I can imagine doing a manske on the raw seeds tea, or the second ph3 liquid, could be different.

 
Jagube
#10 Posted : 2/27/2020 8:56:44 PM

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Jees wrote:
In my limited experience, how well something precipitates under manske is not only salt concentration dependent but also alks concentrated dependent. Do you follow a certain habit which alk concentrations you work with?

The 'habit' I follow is I brew 400g seeds at a time and use between 1000 - 1200 ml water in manske.
These days I don't even weigh my freebase before manske; I just assume it's 30-ish grams. But there is surely some variation in yields from batch to batch, e.g. due to my pH pen playing up.


Jees wrote:
now I get a ton of stuff that stays solid, shaking, time, nothing helps.
Why is this foul looking grey stuff now at ph 3 refusing to go in solution, while it was surely in solution in the raw seed tea at same ph 3, in same sorts of concentration?

Maybe because it's not the same stuff anymore? The base may be causing some irreversible reactions? Just a guess.
 
Homo Trypens
#11 Posted : 2/27/2020 9:51:25 PM

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Jees wrote:
Sometimes this baffles me:
- make a raw tea from seeds, ph like 3, let settle for 24hours;
- decant & make sure no solids come along, dispose solids;
- base the liquid (I goto 12), settle for 24 hours, decant & dispose base liquid;
- add water to solids, now bring solids back into a solution of ph 3

now I get a ton of stuff that stays solid, shaking, time, nothing helps.
Why is this foul looking grey stuff now at ph 3 refusing to go in solution, while it was surely in solution in the raw seed tea at same ph 3, in same sorts of concentration?


Here's three possibilities:
1) tannins are in your tea and crash out with the freebase
2) tiny particles get through your decanting unnoticed, then quill to larger size and sink
3) residual base in your solids reacts with the acid to form insoluble salts

What'll help in each case:
1 before basing) reduce decanted liquid, let cool & settle, decant & filter
2a bb^) let the decanted liquid settle for another 24h then decant again, and/or
2b bb^^) filter your decanted liquid through a coffee filter
3 after basing) wash your freebase before acidifying (add water, let settle, decant water, repeat until water remains almost colorless)
 
Jees
#12 Posted : 2/28/2020 12:01:38 PM

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Jagube wrote:
...The 'habit' I follow is I brew 400g seeds at a time and use between 1000 - 1200 ml water in manske...

Just out of habit I work with half of that concentration, alks of 200 gr seeds represented for 1 liter just before manske. For this I use about 20% salt to be sure to get it all. I was wondering about your 13% being high enough, maybe that's why your second base run delivers precipitation again? So far I could only get a slime from basing the manske filtrate liquid. I was thinking one can't really overdo with salt below 25. But undershooting can. On a practical note I add salt till crystals form even when very hot, then add some water so the crystals only start to form when luke warm during cooling.


Homo Trypens wrote:
...
1) tannins are in your tea and crash out with the freebase
2) tiny particles get through your decanting unnoticed, then quill to larger size and sink
3) residual base in your solids reacts with the acid to form insoluble salts

Homo Trypens, very good points there TY, I think you're down right about 2) and also maybe 1) ?

The pH3 raw seeds tea is very much mirky (even from whole seeds and after 24h settling), as if stuff keeps in floating suspension forever while it is actually perhaps not dissolved in solution. After the BA transition of the tea, the suspension properties seem to vanish and dark grey stuff can finely drop out.
Filtering the raw seeds tea is hard and I actually don't care how/when the stuff comes out, so if that happens in the BA action then that's very fine for me.

Regarding 3) : worked with HCL and NaOH so the formed salts should be NaCL which should stay well in solution.


 
tripwire
#13 Posted : 7/16/2020 11:37:12 PM
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Jagube I too have seen these fine but smaller needles from reducing and re-mansking to be sure i pushed all alks out. I just had a bad feeling about them so would not combine with rest of yield. I see the manske as a making up of a priority order for compounds to fall out. In the case of rue, this means harmine and harmaline are first in this queue. As these get pushed out and the salt concentration increases further under reduction, the next compound in the queue gets forced out.

It is my suspicion and instinct that these are the first of the toxic alkaloids, that under the conditions of the first manske would have stayed in solution.

My suggestion on being sure all the alks are out is to only do a slight reduction and remanske, you can reduce too much and encounter these nasties otherwise.
 
 
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