• Members of the previous forum can retrieve their temporary password here, (login and check your PM).

Seperating Alkaloids

Migrated topic.
N

neurorocket

Rising Star
So SWIM is planning on doing a Phragmites Australis A/B extraction. The problem is that Phragmites seems to have a whole cocktail of alkaloids some, like gramine or bufotenin of which are undesirable. SWIM was thinking of ways that he could separate the good stuff from the bad and thought of using the ph at which they become salts. For example if the ph that gramine turns into a salt is different then the ph of when DMT turns into a salt then after SWIM is done with the A/B he can add any crystals he gets to acidified water and get gramine citrate and freebase DMT and then he could extract the freebase and leave the salt.

So SWIM would like to know, would this procedure work? And if so, at what ph do Gramine, Bufotenin, DMT and 5-meo-DMT turn into freebase or salts.

Also what are the dangers of gramine (why is such a big fuss made about it).
 
What is the pka (SWIM looked it up on wikipedia and it was incomprehensible, maybe SWIY could explain it in more accessible terms), gramine is (according to the research SWIM has done) soluble in the exact same things as DMT and insoluble in the same things. Do different salts (citrate, acetate, hydrochloride) have different solubilities?

Wouldn't a STB with heptane pull all the bad things along with it.
 
The pKa is the pH at which 50% of the alkaloid is in salt form and 50% is freebased.

At pKa -2 1% is freebased and 99% is salted
At pKa -1 10% is freebased and 90% is salted
At pKa +0 50% is freebased and 50% is salted
At pKa +1 90% is freebased and 10% is salted
At pKa +2 99% is freebased and 1% is salted

It’s not completely accurate to go by just the pKa of an alkaloid. There are other factors at play such as solubility of the various salts and the solubility of the freebased compound.

The solubility of various alkaloid salts differ from the solubility of each other and their parent freebase form. For example, DMT freebase is almost insoluble in water while DMT fumarate is water soluble but much less water soluble than DMT acetate; mescaline freebase is water soluble while mescaline sulfate is less water soluble and mescaline hydrochloride is highly water soluble, etc.

I’m sure there is at least one salt form of gramine that has different solubility from the same salt form of DMT. That’s usually the case. It’s just a matter of finding the right salt form and solvent mix.
 
Also consider heat as a form of separation or selective destruction.

For example, bufotenine (which SWIM likes much MORE than DMT) contaminated with DMT can be decontaminated by heating it to 100 C. All of the DMT will vaporize away, leaving behind the bufotenine.

You can also distill alkaloids. For example, if you boil a mix of freebase bufotenine and freebase DMT in water, the DMT will probably vaporize along with the water and I believe most of it will collect in your receiving flask within the distilled water. SWIM never tried that, but believes it will work, because I believe that boiling DMT vapor and boiling water vapor will form an azeotrope. Bufotenine vapor should not form an azeotrope with water vapor because it’s boiling point is way too high. I’m not sure of this though. It’s just a theory and might be wrong.

Some things distill along with water that you wouldn’t expect would. For example, d-limonene distills together with water even though its boiling point is much higher.
 
Is pKa-2 the pKa minus two, or is it a completely different variable (the pKa of DMT is 8.68 so would it be 99% salted at a pH of 6.68 )? How would SWIM find the pKa of gramine?

Where would SWIM find the solubility information for various salts?

Also does anyone have information on the negative effects of gramine.
 
neurorocket said:
Is pKa-2 the pKa minus two, or is it a completely different variable (the pKa of DMT is 8.68 so would it be 99% salted at a pH of 6.68 )?
Click to expand...

Yes at pH 6.68 99% of DMT is salted. At pH 5.68 99.9% is salted. At pH 4.68 99.99% is salted, and so on.

neurorocket said:
How would SWIM find the pKa of gramine?
Click to expand...

You’d first have to isolate it. It’s not going to be easy.

neurorocket said:
Where would SWIM find the solubility information for various salts?
Click to expand...

On forums like this one. Most of the DMT and DMT related salt forms are not documented anywhere. Very little professional work has been devoted to various DMT and DMT related salts. That’s the unfortunate reality.
 
What is the pKb and how is it related to the pKa. Are there ways to find the pKa using the pKb of a chemical.

SWIM found a site that lists the pKb of gramine as 4.33 (chemicaldictionary.org)

SWIM found another site that lists the pKa as 16 (http://www.labseeker.com/cn/ChemicalBiotech/chem-moreinfo.asp?catalog_no=24922) but that site doesn't look very reliable and 16 seems like an extremely high number.

Another site that SWIM found lists some solubility information (GRAMINE [3-(N,N-DIMETHYLAMINOMETHYL) INDOLE]).
 
I highly recommend that whenever you find information like that, that you post the extracted information instead of a link because you never know when those pages might go down and be lost forever.
 
69Ron, I would suggest that you Google "The Plant Alkaloids" by Thomas Anderson Henry. SWIM came across it by accident. It is a book out of copyright that Google has digitized that even though out of date has a lot of valuable information that someone like you might find interesting. SWIM downloaded a .pdf copy that is in a weird Google format that doesn't copy normally. SWIM was looking into Pellotine which is a major alkaloid constituent of peyote that is not contained in San Pedro or Peruvianus.
 
FYI: gramine is slighlty more polar than DMT.

The XLogP3 of gramine is 1.8.
The XLogP3 of DMT is 2.5.

So that means gramine can be separated from DMT by using an extremely non-polar solvent to extract only the DMT. It's possible that heptane might do the job, but probably not naphtha.
 
SWIM has put together a set of teks in order to extract and separate all the alkaloids from the Phragmites Australis. SWIM is hoping that somebody could look over it for any mistakes or things that SWIM may have missed.

This is a basic extraction and freeze precipitation tek (based on the Lextek)

1-Grind Phragmites Australis rhizome and place in HDPE jugs.
2-Acidify distilled water to pH 4 and add to rhizome.
3-Shake and basify pH 11 or 12.
5-Add naptha, separate and put into another glass jar. (SWIM would do 3 pulls).
6-Acidify distilled water to pH 4 and add to naptha.
7-Separate and discard naptha.
8-Basify to pH 11 or 12.
9-Add naptha, separate and put naptha into a glass dish. Discard the water.
10-Evaporate about half of the naptha, then put the dish into the freezer over night.
11-Pour off the excess naptha (evaporate it if you want to make sure you get everything), and dry out the crystals.

This is the separation tek (based on some info SWIM has found on this forum and online)

12-Pour hot heptane onto the crystals and separate (SWIM would suggest using a filter), the DMT and 5-meo-DMT are in the heptane and the Bufotenin and Gramine are on the filter paper.

This a tek for separating the Gramine from the Bufotenin
13-Put the filter paper (with the Bufotenin and Gramine) into a dish of water, and separate it. The Bufotenin should be dissolved in the water and the Gramine should remain on the filter paper. (SWIM would suggest doing this 2 more times).
14-Discard the filter paper.
15-Basify some distilled water pH 11 or 12 and add to the Bufotenine water until no more precipitate forms.
16-Add naptha to the Bufotenin water and separate, discard the water.
17-Freeze precipitate the Bufotenin from the naptha. (Step 9-11).

Use 69ron's tek to separate the 5-meo-DMT from the DMT (Separating 5-MeO-DMT from DMT - Bufotenine and 5-MeO-DMT - Welcome to the DMT-Nexus)

-Would the naptha pull in step 5 get the Bufotenin? If naptha doesn't work are there any other solvents that would do the trick (because SWIM has become interested in Bufotenin after reading a bit about it)?
-Would the naptha pull in step 5 get the 5-meo-DMT?
 
That old 5-MeO-DMT separation tech I posted does not work that well. The results are inconsistent.

Naphtha will not pull bufotenine because it’s insoluble in naphtha. I believe it will pull the 5-MeO-DMT though.
 
Ok, SWIM thinks he'll just forget about the bufotenin for awhile and focus on getting clean DMT and 5-meo-DMT.

Thanks for your help 69ron.
 
Hi,
Firstly you may have noticed that SWIM's username now has an underscore, that's because SWIM is a forgetful fellow and when he cleared his cookies, it signed him out of the forum, and SWIM didn't write down his password.

However SWIM did imagine trying this procedure and ended up with a very small amount of very sketchy looking crystals, which he fed to his pet alligator and produced almost no effect. So SWIM has decided to forget about Phragmites and move onto Phalaris Brachystachys which looks a little more promising.
 
Back
Top Bottom