Isolation of THCA

weedaholic721 · Apr 7, 2015

Ok so I have an idea for a extraction technique that could theoretically yield fairly pure THCa and by extension delta9-THC.

The basis of this procedure relies on the fact that THCa is carboxylic acid. Carboxylic acids generally have a low pka, meaning a weak acid will remove the hydrogen for the carboxylic acid forming an ion that is water soluable. As this is the case a simple 5% Sodium bicarbonate solution should do the job. This technique is very similar to what is used in first semester Organic Chemistry. Due to the face that THCa is what is being isolated freshly cut and dried cannabis would give the highest yields.

Theoretical Procedure:

First the cannabis is extracted normally using solvent of your choice using minimal to no heat during purge to give a perfectly smokable extract. However, as we all know there are still some nonpolar impurities left. The extract is dissolved in a immiscible solvent, like hexane or methylene chloride and added to a separatory funnel. Then you added the 5% Sodium bicarbonate solution to the funnel and mix well, then allow layers to separate. The aqueous layer is separated into flask and organic layer is extracted again with Sodium bicarb solution. Aqueous extracts are combined, organic layer can be saved for followup or discarded.

The combined aqueous solution should now contain the deprotonated THCa. With the addition on an acid, in this case HCl, the THCa will be protonated and will precipitate out of the solution. Any remaining sodium bicarbonate leftover will react with hcl to give NaCl , H20, and CO2 gas. The precipitate can filtered and washed will cold h20 to remove any remain acid plus the NaCl formed.

Product should contain mostly THC acid and can be easily converted to delta9 using heat of a joint, bong or your stove.

The organic layer if saved could theoretically be fractionally distilled to isolate terpenes left over that could be added to THCa at a chosen ratio to give varying effects.

Discussion:

Ok, so it seems like it should work but I have not been able to try as it would require fresh plant material I do not have access too but should be easy to tell if it will work. A small chunk of BHO could be added to water and then add sodium bicarb, if the BHO dissolves then procedure should work.

I just do not have the experience to know if I am missing something major that would cause this procedure not to work. The amount of acid added would have to be determined stoichiometrically (or monitor progression with litmus) as THCa is apparently sensitive to stronger acids but other then that I can not determine why it couldn't be done which is where I leave it to the experts of this site lol

weedaholic721 · Apr 7, 2015

SquattingBull · Apr 7, 2015

While your theoretical chemistry may be possible brother it is impractical and/or undesirable for the extraction world. Methylene chloride is a component of paint stripper and a carcinogen. Hexane is an interesting solvent but a real bitch to use because of how hard it is to purge out and fractional distillation is/has been done. Unfortunately alot of chemistry learned in Orgo lab is not directly applicable or too inefficient to be applied in this manner. Much of what is learned in an organic book is taught for principles sake not because its practical. That is why this thread had gained no traction.

Lastly a cold run extraction with a more efficient hydrocarbon on fresh plant matter is going to yield an extremely high percentage of THCa while leaving the natural terpene profile with little adulterant fats and lipids if done correctly. If an absolute is desired the solution could be dissolved in EtOH and frozen then filtered (which is called winterizing) and thin filmed under a vacuum to yield an extremely smooth and slightly less aromatic compound with very very little adulterant. The key to this procedure being a standard is the use of compounds easy to use and remove that are not known carcinogens or harsh acids.

If you want to get into some interesting chemistry read here, they have done hexane washes and all sorts of interesting protocols you may find interesting.

http://skunkpharmresearch.com/getting-the-green-and-waxes-out-afterwards/

SkyHighLer · Apr 7, 2015

SB, I read it twice yesterday, he thinks he's found an undiscovered simple way to isolate pure THC by first isolating the predominant THC-A from the oil produced from a straight extraction. Methylene chloride, no thank you, please!l

No idea Weedaholic721, but there're are several here that would know, and their silence seems to indicate your idea is ridiculous, or they're too busy checking it out...lol.

weedaholic721 · Apr 7, 2015

Any immiscible solvent would work i.e diethyl ether..just used to dissolve extract to further extract with the sodium bicarbonate solution..since the thca would move to the aqeous layer and the aqeous layer separated..wouldnt there be almost no organic solvent to deal with..and after filtering and washing there should be less then safe limits for trace solvents.

My thought is you take a winterized extract and refine it further.

SquattingBull · Apr 7, 2015

SkyHighLer said:
SB, I read it twice yesterday, he thinks he's found an undiscovered simple way to isolate pure THC by first isolating the predominant THC-A from the oil produced from a straight extraction. Methylene chloride, no thank you, please!l

No idea Weedaholic721, but there're are several here that would know, and their silence seems to indicate your idea is ridiculous, or they're too busy checking it out...lol.

Agree but gonna go with the idea is impractical/ ridiculous. No offense intended to the OP but myself and alot of other people have been through alot more than Organic I in college and as SH pointed out there are people on here that totally outstrip my own knowledge in exponential fashion so I'm just not seeing it.

SquattingBull · Apr 7, 2015

Not to mention that diethyl ether is a a DEA List II controlled substance because of how many other drugs you can make with it. Just as an FYI.

G.O. Joe · Apr 8, 2015

weedaholic721 said:
Any immiscible solvent would work i.e diethyl ether

Ethers are polar enough to extract cannabinoid acids from carbonate solutions. These benzoic acids are weaker acids with higher pKa's than benzoic acid and even carbonate does not extract them well, so your odds with bicarbonate are bad. It's better to use hydroxide instead of bicarbonate, but ethers can still extract THCA from hydroxide solutions. Diols CBDA and CBGA might be a little too salty for ethers, in hydroxide.

There's nothing wrong with DCM. As you have noticed the forum has chemophobic tendencies.

SquattingBull said:
diethyl ether is a a DEA List II controlled substance

So is acetone. It's starting fluid, which can be fractionated. Then, you have you some heptane, and ether that you have added a pinch of BHT to - good things to have if you're doing chemistry.

https://www.icmag.com/ic/showpost.php?p=6315357&postcount=6

Sam_Skunkman · Apr 8, 2015

weedaholic721 said:
Ok so I have an idea for a extraction technique that could theoretically yield fairly pure THCa and by extension delta9-THC.

The basis of this procedure relies on the fact that THCa is carboxylic acid. Carboxylic acids generally have a low pka, meaning a weak acid will remove the hydrogen for the carboxylic acid forming an ion that is water soluable. As this is the case a simple 5% Sodium bicarbonate solution should do the job. This technique is very similar to what is used in first semester Organic Chemistry. Due to the face that THCa is what is being isolated freshly cut and dried cannabis would give the highest yields.

Theoretical Procedure:

First the cannabis is extracted normally using solvent of your choice using minimal to no heat during purge to give a perfectly smokable extract. However, as we all know there are still some nonpolar impurities left. The extract is dissolved in a immiscible solvent, like hexane or methylene chloride and added to a separatory funnel. Then you added the 5% Sodium bicarbonate solution to the funnel and mix well, then allow layers to separate. The aqueous layer is separated into flask and organic layer is extracted again with Sodium bicarb solution. Aqueous extracts are combined, organic layer can be saved for followup or discarded.

The combined aqueous solution should now contain the deprotonated THCa. With the addition on an acid, in this case HCl, the THCa will be protonated and will precipitate out of the solution. Any remaining sodium bicarbonate leftover will react with hcl to give NaCl , H20, and CO2 gas. The precipitate can filtered and washed will cold h20 to remove any remain acid plus the NaCl formed.

Product should contain mostly THC acid and can be easily converted to delta9 using heat of a joint, bong or your stove.

The organic layer if saved could theoretically be fractionally distilled to isolate terpenes left over that could be added to THCa at a chosen ratio to give varying effects.

Discussion:

Ok, so it seems like it should work but I have not been able to try as it would require fresh plant material I do not have access too but should be easy to tell if it will work. A small chunk of BHO could be added to water and then add sodium bicarb, if the BHO dissolves then procedure should work.

I just do not have the experience to know if I am missing something major that would cause this procedure not to work. The amount of acid added would have to be determined stoichiometrically (or monitor progression with litmus) as THCa is apparently sensitive to stronger acids but other then that I can not determine why it couldn't be done which is where I leave it to the experts of this site lol

I am not a chemist but I do know Cannabis, you do not want pure THCA or pure THC it is boring....
You want a high THC terpene rich resin like for example 99.9% resin heads dry sift is. Chemistry does not automatically improve Cannabis, the goal is to keep the goodness and THC and terpenes are needed for this. If chemistry does not achieve this it is not helping. The 99.9% resin heads are mostly THCA, up to 85% in samples I have tested.
Try your method and get back to us with what you think.....
-SamS

youareaniceguy · Apr 8, 2015

Personally I do want pure thca/THC. Pure THC was not boring and was much more medically beneficial for me.

Interesting to read it described as 'boring'.

Sam_Skunkman · Apr 8, 2015

I am a recreational user and believe me pure THC is boring when smoked have you ever smoked pure THC? Maybe you just want to eat it? I have smoked 100% pure THC and I can assure you that dry sift resin that was only 50% is rated by smokers as stronger and better.
As Rob Clarke said when he tried pure THC the first time, "if this was all I got from Cannabis I would not smoke" his words, he found it really boring. It lacks all the different little nuances found in Cannabis. No individuality at all.
I would not waste my time with pure THC any more then a wine connoisseur would drink pure ethyl alcohol, it is just not very good. I understand you think that pure THC will help you but I bet a terpene rich dry sift smoked or eaten is better then pure THC?
-SamS

Gray Wolf · Apr 9, 2015

youareaniceguy said:
Personally I do want pure thca/THC. Pure THC was not boring and was much more medically beneficial for me.

Interesting to read it described as 'boring'.

Haven't had pure THCA, but we've isomerized extracts to convert the CBD present to THC and cooked off most of the mono terpenes in the process.

The bi product had little character from a recreational standpoint, and didn't exhibit clear medical advantage over the base concentrate, so we only did it the one time.

We've also polished extracts, resulting in retention of the companion cannabinoids, but lost most of the monoterpenes and found much the same thing. The character of a cannabis "high" in our experience, is indeed at least the sum total of its parts, if not more.

youareaniceguy · Apr 9, 2015

That is quite different from my own experiences, although I have experienced it many times. Possibly you would have different results if you tried it again.

Did you try it after abstaining from regular cannabis or extracts for a long enough time to make sure you were at baseline?

Its entirely possibly everyone is different, but from my own experiences I could not describe it as boring, unfulfilling, etc. at all.

MostlyMe · Apr 9, 2015

I have a PhD in organic chemistry. The theory of the proposed extraction procedure is sound. However in practice it may be not be so easy to get the deprotonated THCA into the water. We are dealing with a rather large aromatic molecule that even when carrying a charge likely won't be very eager to enter the aqueous phase. It may form vesicle type structures or bilayers on the water-solvent interface, which results in the mixture becoming an emulsion that doesn't separate into phases. There are some tricks to prevent that, but there's no telling if those will work.

I agree with Sam anyway, smoking pure THC is like drinking pure alcohol - not much fun.

Gray Wolf · Apr 9, 2015

youareaniceguy said:
That is quite different from my own experiences, although I have experienced it many times. Possibly you would have different results if you tried it again.

Ummm, possibly, but I haven't talked to anyone who had a different experience with isomerization.

Did you try it after abstaining from regular cannabis or extracts for a long enough time to make sure you were at baseline?

Lawrd no! We're medical patients and none of us have been baseline for at least a decade. We no longer experience "euphoric highs", but can observe what is going on in our bodies, especially our heads.

Its entirely possibly everyone is different, but from my own experiences I could not describe it as boring, unfulfilling, etc. at all.

A good point, and I am only reporting my own experiences, with references to what was reported to me by my lab mates.

Unlike THC Acetate, which we made in class several times and shared with volunteer student test panels, we don't have a broad foundation of responses for just isomerization.

As a measure of us voting with our feet, if it had made the same impression on us three SPR partners as acetalizing, we most certainly would have included it in the class curriculum and subsequent panel testing.

Gray Wolf · Apr 9, 2015

As a side note, we definitely could tell the difference with how much effect was THC and how much effect was "other" with our Alzheimer's patient. She needed CBD for seizures, but when we switched to a 50/50% CBD strain, she became frightened and combative, biting, kicking, punching, and screaming for help.

As soon as higher THC was again administered, she returned to happily babbling, smelling the roses, and passing out hugs and kisses.

Sam_Skunkman · Apr 9, 2015

youareaniceguy said:
That is quite different from my own experiences, although I have experienced it many times. Possibly you would have different results if you tried it again.

Did you try it after abstaining from regular cannabis or extracts for a long enough time to make sure you were at baseline?

Its entirely possibly everyone is different, but from my own experiences I could not describe it as boring, unfulfilling, etc. at all.

First you did not describe if you ate it, smoked it, sub-lingual, up yer keyster, or how?
I tried it many times with and without terpenes, mostly vaped, I know pure THC.
We all took (a dozen subjects) it first thing in the morning before any smoking of Cannabis. and only one test a day, 25mg THC vaped with or without Terpenes all double blind with a 100 question organoleptic survey before and after the test. All subjects were in agreement abut the effects of pure THC. We also tried THC alone and/or with the top Cannabinoids pure, like THCV, and the top ten terpenes with and without pure THC 25 mg THC in each case.

What was the THC you took? I ask because you are the first person that has said they took pure THC? Where did you buy it? What brand? Many people have asked me where they could get it. Mine was a controlled substance I obtained legally here in the EU with a license, but I have special access.
How would you describe it? 100% pure THC? You have not said. Was it compared with a same amount of THC but with terpenes? Like in a dry sift resin or herbal Cannabis?
To me pure THC is boring compared to THC in resin in dry sift, that is great! I did the work with Rob Clarke he and I were in agreement.
All the subjects agreed on pure THC, they were all heavy smokers except one, but he agreed also, they were mostly fairly well know consumers of Cannabis that understand Cannabis very well. Did you ever try pure THCA? Orally? I will let you say what you think before I comment.
The 2nd real proof was 25mg pure THC vaped and then an hour later .25 mg of an equal mix of pure THC and a THC dry sifted resin that was rich in terpenes and was 50 % THC by weight so the mixture was 75% THC, and 25 mg was about twice as strong to subjects then pure THC. The resin does need the right terpenes to potentiate and modify the THC, we used dry sift resin from Skunk #1 it worked.
And all commented that pure THC was flat and boring compared to the same amount of THC in a joint or resin that was also terpene rich.
-SamS

SquattingBull · Apr 9, 2015

Sam_Skunkman said:
First you did not describe if to ate it, smoked it, sub-lingual, up yer keyster, or how?
I tried it many times with and without terpenes, mostly vaped, I know pure THC.
We all took (a dozen subjects) it first thing in the morning before any smoking of Cannabis. and only one test a day, 25mg THC vaped with or without Terpenes all double blind with a 100 question organoleptic survey before and after the test. All subjects were in agreement abut the effects of pure THC. We also tried THC alone and/or with the top Cannabinoids pure, like THCV, and the top ten terpenes with and without pure THC 25 mg THC in each case.

What was the THC you took? I ask because you are the first person that has said they took pure THC? Where did you buy it? What brand? Many people have asked me where they could get it. Mine was a controlled substance I obtained legally here in the EU with a license, but I have special access.
How would you describe it? 100% pure THC? You have not said. Was it compared with a same amount of THC but with terpenes? Like in a dry sift resin or herbal Cannabis?
To me pure THC is boring compared to THC in resin in dry sift, that is great! I did the work with Rob Clarke he and I were in agreement.
All the subjects agreed on pure THC, they were all heavy smokers except one, but he agreed also, they were mostly fairly well know consumers of Cannabis that understand Cannabis very well. Did you ever try pure THCA? Orally? I will let you say what you think before I comment.
The 2nd real proof was 25mg pure THC vaped and then an hour later .25 mg of an equal mix of pure THC and a THC dry sifted resin that was rich in terpenes and was 50 % THC by weight so the mixture was 75% THC, and 25 mg was about twice as strong to subjects then pure THC. The resin does need the right terpenes to potentiate and modify the THC, we used dry sift resin from Skunk #1 it worked.
And all commented that pure THC was flat and boring compared to the same amount of THC in a joint or resin that was also terpene rich.
-SamS

Wow that is an impressive set of experimental data. Thank you for sharing that. Very very cool. Were you performing this for your own purposed, curiosity, ect? Is there any way to have access to that compiled data/ are you hoping to publish it somewhere it could be bought for viewing?

SB

youareaniceguy · Apr 9, 2015

Eaten dronabinol which I am prescribed. I'm aware it is synthetic and coupled with sesame oil.

Also gone through the isomerization process and have tried vaping the extract.

THC acetate as well.

I would describe it as medicinally very beneficial. Antiemetic, anti inflammatory, lowered bp and heart rate.

On another note which pharma are you speaking of? I did have an opportunity to try sativex when I was living abroad however I thought that contained CBD as one of its main selling points over dronabinol.

Sam_Skunkman · Apr 9, 2015

I knew that terpenes modified THC I have felt that for decades, this was the first chance I had to test my hypothesis. Rob was in agreement with me. I think I will publish it in O’Shaughnessy’s as Fred is a friend and they have wanted me to publish it for years. Until then you need to wait. When you see the list of subjects you will understand why we waited, at their request.
The work started 15 years ago with the first 100% pure THC 25 mg being tried by vapeing by just me and Rob, then we tried 25 mg of a 50/50 mixture of pure THC and dry sifted resin that was 50% THC, and 25 mg of the 75% THC mix was stronger then the pure THC. We thought we knew why..... we were right.
-SamS

Isolation of THCA

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