Mescaline: Basifying and d-limonene after hot water extraction

[shroombee]

Hi All. I know this post belongs in the Cacti preparation subforum, but I can't post there yet.

I've done plenty of d-limonene mescaline extractions with Peruvian Torch. I only get around 0.6% yield which I believe is low considering the potency when I prepare the Torch as a tea. So perhaps the tek just isn't that efficient or my execution of the tek is subpar. I was thinking of trying a hot water extraction like this:

Pure mesc compared to tea/resin - Preparation - Welcome to the DMT-Nexus

Then continuing with the lime/d-limonene tek. I've read a lot of posts on mescaline extraction and wasn't able to find whether this process has been tried. Apologies if I missed the discussion. Any thoughts before I go ahead?

 

[Loveall]

I think usual yield issues are not from getting the mescaline into water (but it could be). Usual issues are getting the mescaline in and out of the Limonene (at least for me).

Do you use the paste lime and limo tek? Do you warm the limo when pulling?

For troubleshooting, I would do an extra limo pull and see if mescaline still comes through. Also would check pH of slightly acidified water during salting (if it increases it is a sign of FB mescaline is still moving from Limonene to water).

0.6% is not too bad. If you don't find a way to improve yields, mising potency compared to tea could come from other alkaloids that are not part of the Limonene extraction. Since you are using your tea as your potency reference, you could use half of a tested tea batch as a starting point for an A/B extraction (instead of a separate/new hot water extract). Heat should resolve emulsions in your tea during the process if you are worried about that (from a warm water bath, never an open flame).

Cheers and good luck.

 

[shroombee]

I think usual yield issues are not from getting the mescaline into water (but it could be). Usual issues are getting the mescaline in and out of the Limonene (at least for me).

Do you use the paste lime and limo tek?

Yes I use the paste tek (69ron's food safe tek). I was thinking yield issues might be due to the mescaline not migrating from the cactus goop into the limonene. And the longer we let the cactus goop sit, the more limonene gets stuck in the cactus, further exacerbating the issue.

By using hot water extraction first, I could then focus on getting mescaline to migrate into and out of the limonene. I've read that the mescaline malate salt is highly soluble in water so I'm assuming I can at least get most of the mescaline out of the cactus and into water.

Do you warm the limo when pulling?

Is warming the limonene supposed to help us retrieve it from the goop? Or is the thinking that freebase mescaline is more soluble in warm limonene?

I have tried warming the goop/limonene when pulling, but I don't get anymore limonene out. I've also tried adding washing soda, which didn't help. I added KOH one time and that forced a lot of limonene out of the goop. The goop immediately shriveled up and limonene oozed out. Kind of cool to see it happen. However, I'm not keen on using caustic chemicals these days. This KOH test was done on some cactus goop that was ready to be thrown out, so I didn't bother to salt the recovered limonene, thinking mescaline content was minimal.

For troubleshooting, I would do an extra limo pull and see if mescaline still comes through. Also would check pH of slightly acidified water during salting (if it increases it is a sign of FB mescaline is still moving from Limonene to water).

I'm typically doing up to 4 pulls (probably overkill) and waiting a long time between pulls, thinking more mescaline will migrate into the limonene. This might be counterproductive because the longer wait time means more limonene gets stuck in the cactus and I have to add more limonene to keep my limonene recovery at 300 ml.

I'm currently salting using 100 ml water with 8 drops of 5% HCl added. Spin with the magnetic stirrer for 5 minutes, let sit 5 minutes, separate, then wait 5 minutes to allow pH to stabilize. I'll continue salting until pH is below 6.5. Typically 3 saltings will do it with the last one resulting in a pH well below 6.5.

Since you are using your tea as your potency reference, you could use half of a tested tea batch as a starting point for an A/B extraction (instead of a separate/new hot water extract).

I'll try something along those lines. By A/B extraction, you mean next step is to basify the tea, correct? I wouldn't think there is a purpose of adding acid to the tea at this point.

Thanks for your insight!

 

[Loveall]

Sounds like you are doing it all properly to first order.

I don't think 4 limo pulls is overkill. I would suggest you do a few more after that and see what you get, you may find some yield there. Warm limo has helped me get more Limonene out before, but it doesn't seem to be the case for you. I'm not sure if the partition coefficient is better when warm, but since you may be missing yields I would try it.

What I do now a days is start with rOm's tek and microwave (using a mason jar). It is stinky (ammonia smell) but I haven't had any issues. I also add table salt. I like the paste it gives. Some way that FB mescaline could be damaged with heat, but I have not noticed that. For me this paste is more workable and does not not hold to the Limonene much.

And yes, for the tea, I meant drink half the tea and the other half basify and extract to compare effects and see if the extraction is much weaker or not.

 

[doubledog]

I'm currently salting using 100 ml water with 8 drops of 5% HCl added. Spin with the magnetic stirrer for 5 minutes, let sit 5 minutes, separate, then wait 5 minutes to allow pH to stabilize. I'll continue salting until pH is below 6.5. Typically 3 saltings will do it with the last one resulting in a pH well below 6.5.

This probably means that your first salting has quite high pH and mescaline is extracted into water as a freebase. Your outcome depends on what you'll do next, but it is better to salt out to pH 6.5 with your first salting.

 

[Loveall]

I'm currently salting using 100 ml water with 8 drops of 5% HCl added. Spin with the magnetic stirrer for 5 minutes, let sit 5 minutes, separate, then wait 5 minutes to allow pH to stabilize. I'll continue salting until pH is below 6.5. Typically 3 saltings will do it with the last one resulting in a pH well below 6.5.

This probably means that your first salting has quite high pH and mescaline is extracted into water as a freebase. Your outcome depends on what you'll do next, but it is better to salt out to pH 6.5 with your first salting.

I was thinking "continued salting" meant adding more sulfuric drops to titrate down to pH6.5, but after reading again it looks like fresh sulfuric is used each time.

shroombee, do you combine your saltings and measure that pH? To doubledogs's point any mescaline in FB form won't crystalize from for example acetone/water. dg's procedure works great.

 

[shroombee]

I do multiple saltings with fresh HCl water (not sulfuric) each time, and I measure the pH after each separate salting to know when to stop salting. I am not currently titrating down to pH 6.5. I've done that in the past and I find it to be tedious. But perhaps you are saying that titrating a single salting is far superior than multiple saltings?

After pulling and salting, I evaporate the saltings separately in a dehydrator at 95 degrees. Takes several hours. Then scrape up the slightly waxy pencil shavings. I don't combine saltings so that I can measure yield off each pull+salting.

I was not aware that FB mescaline would migrate to the water. I thought it would stay in the limonene and only jump to the acid water if there is enough acid present?

So are we recommending titrating to pH 6.5 and using dg's procedure of adding acetone to force precipitation of pure crystals? And this is more desirable and reliable than evaporating? Is sulfuric or HCl the current best choice? I use 5% food grade HCl in the form of stomach acid drops.

Thanks so much Loveall and doubledog for the help!

 

[Loveall]

I do multiple saltings with fresh HCl water (not sulfuric) each time, and I measure the pH after each separate salting to know when to stop salting. I am not currently titrating down to pH 6.5. I've done that in the past and I find it to be tedious. But perhaps you are saying that titrating a single salting is far superior than multiple saltings?

After pulling and salting, I evaporate the saltings separately in a dehydrator at 95 degrees. Takes several hours. Then scrape up the slightly waxy pencil shavings. I don't combine saltings so that I can measure yield off each pull+salting.

I was not aware that FB mescaline would migrate to the water. I thought it would stay in the limonene and only jump to the acid water if there is enough acid present?

So are we recommending titrating to pH 6.5 and using dg's procedure of adding acetone to force precipitation of pure crystals? And this is more desirable and reliable than evaporating? Is sulfuric or HCl the current best choice? I use 5% food grade HCl in the form of stomach acid drops.

Thanks so much Loveall and doubledog for the help!

With HCl you should evaporate like you are doing. Dg's procedure is for sulfuric saltings, where the acetone precipitation will give a purer product as the xtalization is more selective than evaporating the water.

FB mescaline will move into the water if you don't use enough HCl. This is because FB mescaline is soluble in both limonene and water (see partition coefficient). Note that this is not the case for mescaline salt: because it is only soluble in water it won't distribute itself between the solvent and water at equilibrium and will only be in the water. Your first salting could be more waxy/oily if it contains FB and you will measure a slightly different mass vs all salt. Also, your last salting with very low pH may look different/dirtier after evap since you could start salting plant stuff with lower pKa. Finally, by doing multiple water saltings you are soaking up non-salts that are soluble in both limonene and water into the water (like doing multiple pulls but in reverse). I prefer to do one salting to pH 6.5, yes it is a bit of work but not too bad, you can sample the water as you go (return it to the mix) and do one separation.

Do you have any data for your process? In particular, any info on each limonene pull yield? We can estimate total mescaline and how many pulls to do based on the first two solvent pulls (this is a crude partition measurement roughly valid long as they are not saturated which I don't think happens with water/limonene).

Also, not as important, but interested in each salting yield measurement.

 

[doubledog]

I also do one titration to pH 6, and use liquid pH indicator (home made from red cabbage), added to water.
Then just count drops of acid and watch colour.

FB mescaline is quite soluble in water and it make water moderately basic.

 

[shroombee]

Okay I'm learning a lot here. I wish these best practices were rolled into an updated mescaline extraction tek. I've read a lot of posts but never came across these simple principles to optimize the food safe extraction tek:

1) Each salting will pull non-salts into the water along with the mescaline. So multiple saltings should be avoided. Either titrate to pH 6.0-6.5 which will get about 90% of the mescaline into the water, or use excess acid (how much?) to ensure pH will be well below 6.0 (easier but less desirable because you get more crud with the mescaline);

2) Freebase mescaline is soluble in water. To avoid FB mescaline from showing up in your end evaporation, as above either titrate or use excess acid. Going forward, I'll go with the titration;

3) Use liquid pH indicator to simplify titration. Google "red cabbage ph indicator" to make your own. Amazon has red cabbage powder for making ph indicator, which looks convenient to use and store;

4) Use HCl if you're evaporating, use sulfuric for acetone xtilization;

By the way, as the acid (say 5% HCl) is being dropped into the limonene/water mix to titrate it down to pH 6.5, does that concentrated drop of acid pull crud as it is dropping through the top layer of limonene? Maybe the answer is yes in theory, but it's a trivial amount?

FB mescaline is quite soluble in water and it make water moderately basic.

What motivates the FB mescaline to migrate to the limonene from the cactus which has been basified with water and lime? And does this process thus require time? It would seem that at least a moderate amount of FB mescaline would remain in the cactus unless several pulls with limonene are done? In other words, a single pull can only get a limited amount of the FB mescaline since the FB mescaline is happy staying with the water in the basified cactus?

Do you have any data for your process? In particular, any info on each limonene pull yield?

Let me check my notes for yield data. I just started taking better notes so I'll have to see if I have good data that relates to a known process. I will soon do some controlled experiments where I will collect good data and post for the community.

 

[downwardsfromzero]

What motivates the FB mescaline to migrate to the limonene from the cactus which has been basified with water and lime?

Mescaline's three methoxy groups contribute significantly to its polarity which increases its water solubility. It being a primary amine is also a factor - compare the solubility of freebase (plain, vanilla) phenethylamine:

Phenethylamine

Phenethylamine | C8H11N | CID 1001 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.

pubchem.ncbi.nlm.nih.gov

The rest of your question is what partition coefficients are all about. Loveall has posted fairly extensively on this topic around here somewhere.


And, just a friendly reminder about the rules:

Please have another read of this: 2.2 No discussion on selling, buying, sourcing, acquiring, pricing, trading, receiving, distributing, mentioning pending deliveries or smuggling of drugs [emphasis added]

- especially wrt the last sentence of your previous post. Dried plant material is included in the category concerned.

 

[shroombee]

And, just a friendly reminder about the rules:

Please have another read of this: 2.2 No discussion on selling, buying, sourcing, acquiring, pricing, trading, receiving, distributing, mentioning pending deliveries or smuggling of drugs [emphasis added]

- especially wrt the last sentence of your previous post. Dried plant material is included in the category concerned.

Sorry I didn't realize this section refers to dried plant material. I sincerely apologize. I have corrected the error in my post. Thanks for bringing this to my attention!

 

[Loveall]

shroombee, feel free to summarize and update any concepts that are not documented well. The nexus is what we make of it. The mescaline Teks are a little dated and maybe a fresh update would be good.

Anything that is soluble in both phases will be in both. However, there will be a concentration ratio (partition) driven by the chemical potential (which you can read about). I think some people jump to the erroneous conclusion that because salt is not soluble in solvent, then conversely, the FB is not soluble in water. If I recall, ron69 was washing his limo with basic water until he figured out he was pulling FB mescaline into the water and losing product. When people do wash with the solvent with water they typically use brine to saturate the water with ions and make it less likely for FB to go in it (minimize losses). I believe we have a DMT Tek in the Wiki (Noman's?) that uses carbonate water washes, it doesn't yield as well as other Teks but it is designed for purity I believe.

Intuitively, the molecules diffuse to occupy the entire volume if they can. Kind of like a a gas diffusing between two rooms.

When you do multiple pulls, the situation is equivalent to a bouncy ball that looses a fraction of it's energy after each bounce (perhaps this is more intuitive?). How many pulls you need to remove product ammount X is equivalent to how many bounces you need to remove energy (or bounce height) X.

For example, imagine a ball that looses 40% of it's energy with each bounce (that is, each bounce is 60% as tall as the previous height). Starting with from a height of 100 inches,

-After one bounce, the ball reaches 60 inches (40 inches lost = 40% yield after one pull)
-After the second bounce, the ball will reach 36 inches (24 lost in this bounce + 40 from before is 64 inches total lost = 64% yield after second pull).
Note: After or two bounces we can tell how big the initial height is, even if we never saw the initial position of the ball. In other words, we can estimate the total amount of product by measuring the first two pulls: 40 in the first pull (M1) and 24 in the second pull (M2) can estimate the total amount of product (MT) with the simple formula MT = M1^2/(M1-M2) = 40^2/(40-24) = 1600/16 = 100. I think this is kind of cool.
- After three bounces, ball will bounce 21.6 inches (14.4 lost on this point). The height (energy) removed is now 40 + 24 + 14.4 = 78.4.
- What happens after the 4th bounce is left to the reader. Finally after 5 bounces, the height (energy) removed is 92.224, equivalent to 5 pulls yielding 92.224%.

It's fun that the bouncing ball is mathematically equivalent to pulling drugs. It gives a new meaning to "I'm as high as balls"

 

[shroombee]

feel free to summarize and update any concepts that are not documented well. The nexus is what we make of it. The mescaline Teks are a little dated and maybe a fresh update would be good.

I will start another post in the appropriate forum to facilitate collecting the latest principles and best practices for mescaline extraction. Hopefully this will lead into an updated tek or two.

I think some people jump to the erroneous conclusion that because salt is not soluble in solvent, then conversely, the FB is not soluble in water.

I erroneously thought that FB mescaline was nonpolar, like oil, and would not migrate to water.

If I recall, ron69 was washing his limo with basic water until he figured out he was pulling FB mescaline into the water and losing product.

And the purpose of this is to remove some of the water soluble stuff before salting, so less unwanted stuff migrates to the salting water?

Intuitively, the molecules diffuse to occupy the entire volume if they can. Kind of like a a gas diffusing between two rooms.

I think I understand the concept as two rooms (or boxes) of a different size. Take two boxes, one is 60 cubic ft, the other is 40 cubic ft. Allow the gas to diffuse between the two boxes. Evacuate the 40 cubic ft box. Allow the remaining gas to diffuse between the two boxes again. Evacuate the box again. Et cetera.

In the case of FB mescaline diffusing across water and limonene, I assume the FB mescaline has a different affinity to water versus limonene. So there is some sort of affinity variable as well as the actual volume of the two liquids. And then anything that slows down the diffusion process such as cell walls. Taking these factors into account would allow us to estimate a ratio of water to limonene that is efficient for pulling. At least this is how I imagine it, not knowing anything about organic chemisty. :?:

MT = M1^2/(M1-M2)

This is very cool!

 

[Loveall]

If I recall, ron69 was washing his limo with basic water until he figured out he was pulling FB mescaline into the water and losing product.

And the purpose of this is to remove some of the water soluble stuff before salting, so less unwanted stuff migrates to the salting water?

Yes

Intuitively, the molecules diffuse to occupy the entire volume if they can. Kind of like a a gas diffusing between two rooms.

I think I understand the concept as two rooms (or boxes) of a different size. Take two boxes, one is 60 cubic ft, the other is 40 cubic ft. Allow the gas to diffuse between the two boxes. Evacuate the 40 cubic ft box. Allow the remaining gas to diffuse between the two boxes again. Evacuate the box again. Et cetera.

In the case of FB mescaline diffusing across water and limonene, I assume the FB mescaline has a different affinity to water versus limonene. So there is some sort of affinity variable as well as the actual volume of the two liquids. And then anything that slows down the diffusion process such as cell walls. Taking these factors into account would allow us to estimate a ratio of water to limonene that is efficient for pulling. At least this is how I imagine it, not knowing anything about organic chemisty. :?:

Well said, but don't worry about the speed of the diffusion too much, as long as you give it enough shaking/time you will reach equilibrium. The variables are affinity (related to electrochemical potential) and volume. There is also the cool idea of "effective volume": if you multiply the solvent volume by the partition coefficient then you work in a space where everything can be thought of as a simply volumes (two rooms of different sizes where diffusion is taking place). Look at the image below, where the green compound has more afinity for the solvent. Now imagine in your mind shrinking the solvent volume so the green color intensity is the same: that is the effective solvent volume.

If you have a 60:40 (water: solvent) partition and you double the solvent volume, you can predict the new ratio as 60:80 (this is easy to see if you think of two rooms with gas in equilibrium and then double the size of one of them). This new ratio is equivalent to 43:57, which shows the pull yield increases by 17%, from 40% to 57%). The two volumes of solvent were better used in our previous example, where after two separate pulls we were at 64% yield, but it is more work to pull twice so there is a trade-off.

Can you estimate the increase yield for a 60:40 system if the water was boiled down to half its volume (this is nice, but in practice it can't always be done because of the gunk factor).

When warming up the system, we are changing the affinity (which can be thought of as changing the "effective volume" of the solvent). The affinity goes up for both water and Limonene with temperature, but if it goes up faster for Limonene the partition for the pull would be better. No change to the extraction if the affinity goes up the same for both, and worse if it goes up more for water (this is unusual as solvents are more sensitive to temperature). When we add a lot of salt to the water, we are stuffing one of the rooms, lowering the affinity in the water to improve the partition (can also be thought of as decreasing the effective volume of the water).

MT = M1^2/(M1-M2)

This is very cool!

I think so

Keep in mind the formula's limitations: assumes the solvent is not saturated, assumes same conditions between pulls (limonene volume, temperature, equilibrium is reached, ect). Also, there is some experimental error when measuring the yield of each pull that propagate in the formula (it's not ideal to subtract similar quantities). However, I think it can be a good estimate from experience and Elrik also showed this experimentally in one example.

 

[doubledog]

1) Each salting will pull non-salts into the water along with the mescaline. So multiple saltings should be avoided. Either titrate to pH 6.0-6.5 which will get about 90% of the mescaline into the water, or use excess acid (how much?) to ensure pH will be well below 6.0 (easier but less desirable because you get more crud with the mescaline);

Multiple pulls are not necessary, and it's also better to use less water, as you are going to evaporate it in the next step.
Titration to proper pH is preferred, but too much acid is not a big issue even with sulphuric acid. You can get rid of it by re-x.

Drying of nonpolar before salting really improve purity. For xylene, few grams of dry NaOH will do it, I am not sure what is best for limonene. Maybe simple NaCl?

3) Use liquid pH indicator to simplify titration. Google "red cabbage ph indicator" to make your own. Amazon has red cabbage powder for making ph indicator, which looks convenient to use and store;

Very simple and convenient tool, but re-x or washing is needed, it won't evaporate.
Liquid could be stored frozen in ice cubes, just few mililiters are needed for each extraction cycle.

By the way, as the acid (say 5% HCl) is being dropped into the limonene/water mix to titrate it down to pH 6.5, does that concentrated drop of acid pull crud as it is dropping through the top layer of limonene? Maybe the answer is yes in theory, but it's a trivial amount?

Yes, of course, but you do not have any different option how to transport acid drop into the water without contact with nonpolar phase.

What motivates the FB mescaline to migrate to the limonene from the cactus which has been basified with water and lime? And does this process thus require time? It would seem that at least a moderate amount of FB mescaline would remain in the cactus unless several pulls with limonene are done? In other words, a single pull can only get a limited amount of the FB mescaline since the FB mescaline is happy staying with the water in the basified cactus?

FB mescaline is soluble in neutral water, but is less soluble in basic water.
You should also take into account that you have cactus solids in the mix, which definitely slow down the migration.

 

[Loveall]

Drying of nonpolar before salting really improve purity. For xylene, few grams of dry NaOH will do it, I am not sure what is best for limonene. Maybe simple NaCl?

What I do with limonene is let it rest overnight or longer until it is clear. Very tiny water droplets seem to form at the bottom and tend to stick there (easily decanted).

 

[mrdub]

feel free to summarize and update any concepts that are not documented well. The nexus is what we make of it. The mescaline Teks are a little dated and maybe a fresh update would be good.

I will start another post in the appropriate forum to facilitate collecting the latest principles and best practices for mescaline extraction. Hopefully this will lead into an updated tek or two.

:thumb_up:

Interesting thread, I've got some reading to do

 

[shroombee]

Can you estimate the increase yield for a 60:40 system if the water was boiled down to half its volume (this is nice, but in practice it can't always be done because of the gunk factor).

If we boiled down the water to half its volume from a 60:40 system, we would be at 30:40. Equivalent to 43:57. Thus (assume we started with 100 mg of product to extract):

Pull #1:
57% of 100mg = 57mg pulled (total 57mg extracted)
100mg - 57mg pulled = 43mg remaining

Pull #2:
57% of 43mg = 24.5mg pulled (57 + 24.5 = total 81.5mg extracted)
43mg - 24.5mg pulled = 18.5mg remaining

Pull #3:
57% of 18.5mg = 10.5mg pulled (57 + 24.5 + 10.5 = total 92% extracted)
18.5mg - 10.5mg = 8mg remaining

When warming up the system, we are changing the affinity (which can be thought of as changing the "effective volume" of the solvent). The affinity goes up for both water and Limonene with temperature, but if it goes up faster for Limonene the partition for the pull would be better. No change to the extraction if the affinity goes up the same for both, and worse if it goes up more for water (this is unusual as solvents are more sensitive to temperature). When we add a lot of salt to the water, we are stuffing one of the rooms, lowering the affinity in the water to improve the partition (can also be thought of as decreasing the effective volume of the water).

So the lessons here:
1) Reduce the volume of water (tea);

2) Warm up the system to increase the affinity of FB mescaline to limonene more than that of water. To know whether this is efficient in practice, we'd like to know:
(a) the affinity of FB mescaline to water as a function of temperature, and
(b) the affinity of FB mescaline to limonene as a function of temperature;

3) Add salt to the water. What kind of salt, how much, and does the salt dissociate and migrate over to the limonene, thus contaminating our end product when we salt the limonene with acid?

 

[shroombee]

3) Use liquid pH indicator to simplify titration. Google "red cabbage ph indicator" to make your own. Amazon has red cabbage powder for making ph indicator, which looks convenient to use and store;

Very simple and convenient tool, but re-x or washing is needed, it won't evaporate.
Liquid could be stored frozen in ice cubes, just few mililiters are needed for each extraction cycle.

Other than to remove the color, is there any other reason to remove the pH indicator if I don't mind consuming the evaporated product?

By the way, as the acid (say 5% HCl) is being dropped into the limonene/water mix to titrate it down to pH 6.5, does that concentrated drop of acid pull crud as it is dropping through the top layer of limonene? Maybe the answer is yes in theory, but it's a trivial amount?

Yes, of course, but you do not have any different option how to transport acid drop into the water without contact with nonpolar phase.

Pull the water with a syringe, squirt into a second beaker to test the pH. Add the acid drop to the beaker. Pull with a syringe and squirt back into the water layer of the first beaker. Probably overkill!

Interesting thread, I've got some reading to do

Yes - very helpful information here!