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Author: Subject: possibility for THC extraction
Mendeleev
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possibility for THC extraction

Okay, I realize this is somewhat of a controversial topic because this is not a drug forum, but this is chemistry related. If the mods feel it is innapropriate please remove it. Okay, here goes:

I was wondering if it would be possible to extract pure THC from marijuana. I'm sure there must be some sort of series of solvent extractions that can be done much like the purification of morphine from opium or cocaine from coca. So far I can only speculate on how to do this with THC. I know however that THC is insoluble in water but soluble in oil.

I propose something along the lines of the following: About a quarter pound (\$200) of some low quality marijuana is ground up with a mortar and pestel to a powder consistency. Boil about a liter of water and drop all the herb in it to boil for 10 minutes, then vacuum filter on a very fine filter, while hot. This should remove all the water soluble junk.

Next you need to get rid of the plant matter: leaves, stems, etc. Sulfuric acid is probably the optimum candidate for this, so the residue on the filter is added to 1L 35% sulfuric acid and left to stand for a little while then filtered. I am not sure about this step because I do not know if THC dissolves or undergoes a reaction with sulfuric acid. Assuming this step works what you have left is THC, with a few other chemicals, as most of the plant matter and water soluble crap has been removed.

Final step extract the THC with a solvent that is THC specific. I do not know what such a solvent is, but THC is soluble in oil(cooking) so this is a possibility. Evaporate the solvent under vacuum(this is why oil might be a bad choice) and you should be left with pure THC. Again I have made quite a few assumptions and perhaps this process will not work, but I'm sure there is definitely some way it can be done.

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Reverend Necroticus Rex
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Best way, is to finely powder your green goodness, pack it in a long narrow tube, and vent liquid butane down it, make sure the tube has a screen on the end to catch particulate matter.

Butane is an excellent solvent for cannabinoids, and the resulting honey oil is in the 90% THC range I believe, and the inactive cannabinoids also extracted can be isomerised to delta-9-THC by the right treatment with concentrated H2SO4.

Yields are quite low, but is well put to use if you have ounces, halfs, or even masses of shade leaf from growth, I got a few drops of oil from one ten bag (UK) of good potency skunk, but a droplet less than a match head in size smoked in my pipe, well, incapacitated would be the correct term to use

And DO use high quality pot if you were,theretically of course, to dream of doing that, as they say, garbage in, garbage out

[Edited on 16-1-2005 by Reverend Necroticus Rex]

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S.C. Wack
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You will find more answers in a pot forum.

http://www.overgrow.com/edge/forumdisplay.php?daysprune=&for...
PainKilla
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THC is basically impossible to extract in crystal form as it's been proven that it does not like to form crystal masses. So, oil would be what you are looking for... The butane extraction is supposed to work well, but a solvent extraction works just as well too. Acetone, and alcohol's extract THC well. Acetone does get some other unneeded stuff too, (chlorphyll tannins etc) so Ethanol would be reccomended.

Also, soaking your marijuana in a mild high ph (like 8-10) results in decarboxalation of the THC-COOH, which remains inactive, to THC; other cannabinoids seem to undego this process too. The H+ protonation seems to rotate the the low order THC's into the delta 9/8/1/6. A most useful technique .

BTW, I was wondering whether anyone had information on the production of THC acetate, which is supposedly more potent. It is made via reflux of acetic anhydride and pure THC (oil).
Blind Angel
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According to the merck it constitue only 1% of the plant material and there's a reference too:
Isolation of Delta1-3,4-trans-form from marihuana: Gaoni, Mechoulam. J. Am. Chem. Soc. 86, 1646 (1964)

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PainKilla
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Actual THC is only 1%, but cannabinoids make up a lot... I had a reference somewhere, Ill try and find it.... not realting to this but:

hermes did you ever do that synth of acetic anhydride via Na-acetate and co2?

Ill be trying it in a few days (waiting for my mixture to evaporate :p )
JustMe
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Best solvent for said compound is Chloroform. Don't ask/don't tell.
Dodoman
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 Quote: Research has shown that chloroform is the best solvent in the extraction; it extracts 98% of cannabinoids with one half hour of shaking

This quote is from a file called "Michael Starks - Marijuana Chemistry [Genetics, Processing & Potency].pdf" you can find it on the ftp.

It also sugessts to further purify by shaking the organic layer with water and separating the two layers. This is clearly better than your idea Mendeleev because if you boil with water first you'll make it harder for the organic solvent to infeltrate the fibers of the plant cause it'll be filled with water.
S.C. Wack
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What about the chlorophyll? I believe that is why pet. ether is so used. BTW, the THC is on the surface of the plant.
PainKilla
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Acetone works well too, its just that it extracts everything... Im serious it rips apart the whole plant and you get left with celluose basically. It is good for using to add H+ into though .
Mendeleev
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Wow, I am pleasantly surprised by all the replies . This is good. I guess the process goes something like: soak cannabis in liquid butane or chloroform or maybe even petroleum ether for a little while, say an hour, then filter, then wash with water a couple of times or maybe even wash with NaOH to decarboxylate the THC-COOH like PainKilla said. Liquid butane has the advantage that it is very easy to evaporate off.

 Code: According to the merck it constitue only 1% of the plant material

Maybe 1% of the entire plant or maybe in very low grade cannabis which is cultivated for the hemp and not the smoke, however many high quality strains have more than 20% THC.

Is it really impossible to crystallize THC? I was hoping it would be possible to insufflate it.

[Edited on 16-1-2005 by Mendeleev]

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S.C. Wack
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The 1% that Merck refers to is on the delta-6 isomer.
Mendeleev
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http://www.marinol.com/marinol02.html

Holy shit, synthetic THC pills! First time I ever heard of this!

I looked on the cannabis forum, the extraction is pretty straightforward, pack a long thin tube with a screen on the end with cannabis and spray 8 times the weight of butane down it. Let it stand and vaporize and you've got THC oil.

Trogdor was a man. A dragon man. Or maybe just a dragon. . .
PainKilla
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DON"T ingest the THC from marinol. it is not the kind you think it is. The marinol removes many of the "good" parts of marijuana and is in fact often scolded by users, who prefer medical marijuana (smoked) to trea their symptoms. I reccomend using NaHCO3 as it is more mild and has lesser chance of having heavy metals and all that (unless you have ACS grade.) My freind Jesus, almost has a batch finished.... PM "Jesus" for details.

----EDIT, anyone have information on THC acetate, this is the best I could find---

[Edited on 17-1-2005 by PainKilla]
JustMe
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painkilla,

Wow, I remember reading that same article/book many, many, MANY moons ago. Really takes me back, way back. LOL

Thanx... for the memories (cue the music).
enima
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Solvents...

Butane for a supercritical extraction (best)
Hexane works well as a general solvent

Alcohols and Acetone will result in a very dirty extraction. Stick to the two above.
Darkfire
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NaOH can realy do a decarboxilation? I've always thought they were the high temp and pressure type of reaction.

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sparkgap
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The only decarboxylations I know that good old caustic soda can do at easily attained conditions is decarboxylation of carboxylic acids with carbonyl groups one carbon away (to be precise, beta-keto acids). That's the final step in the malonate and acetoacetate type syntheses.

I have yet to see the structure of THC acid, so I'm just speculating. Maybe it has that special moiety...
S.C. Wack
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It is allegedly as easy as refluxing in solvent, or heating the plant material without solvent, but I have no refs other than the underground word. I bet decarboxylation would give a few hits at overgrow.
PainKilla
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Baking soda works at doing this, a mild pH of about 9 causes decarboxalation in THC acid. Rotation of higher order THC (like delta 9 etc) is causes by H+ protonation is a solvent. "Jesus" performs these procedures quite often and redeposits it on the bud, using acetone. The result is a pale "sickly" looking bud, that has visible crystal growth all over it .
CycloKnight
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Mood: Still waiting for the emulsion to settle.

Extraction of psychoactive material from cannabis

I've carried out the soxhlet extraction of the psychoactive ingredients of cannabis at least a dozen times in the past.
I deleted most of my original photos, but just by chance I found this one still on my camera.

I found that a simplified procedure for the extraction of pure cannabis oil (not pure THC, but still extremely potent) could be used that was quite effective, and produced a thick, translucent yellow oil, essentially the same as "honey oil".

This is how I did it:
1) Soxhlet extract cannabis for several hours using "dry" ethanol as solvent. That's right, ordinary ethanol (as dry as possible, 95% should be okay).
2) Filter it really good. I used vacuum filtration. Colour will be medium to dark green.
3) Now the magic part and this is why you can use ethanol do the extraction: Combine with activated carbon, mix it good and filter. Repeat this again. You will now be left with a very light yellow tincture! All chlorophyll has now been removed.
4) Distill off the solvent entirely under vacuum using a vigreux column to minimise product carry-over. This also removes the water which will be present from the extraction. If you do not have a vigreux column or equivalent, just distill very slowly - it will help to contain you product in the boiling flask. You will now be left with a rich, deep golden coloured slightly viscious liquid.
This next step is optional. If you feel it necessary, you may combine this liquid with a suitable organic solvent (ether, toluene, ect) and wash with dH2O, then back-extract that dH2O to minimise your losses. This will remove salts that have be extracted from the plant material. The organic solvent is then removed by vac. distillation and then continue with step 5. The necessity of this extra step depends on 3 factors:
a) Quality of plant material, was it well cured, was it full of fertilizer before extraction? If so, do the wash. If a relatively large volume of plant material was extracted (i.e. leaves, trimmings, swag, etc), then do the wash.
b) Was ethanol dry? The drier the less salts that will have been pulled out.
c) Are salts going to be an issue? In practice I've found that the nitrate that gets pulled into the oil actually makes the final oil burn alot better. Organic material (whatever) that has been impregnated with ToC will burn much better than oil which has had all the salts removed.

5) Dilute with pure ethanol (non-denatured, use non toxic type!) to make up "Tincture of Cannabis". Inject it into ordinary "sticks" of organic (can I say "herbal"?) material to make what are known as "Reefers" (preferably the kind without filters), not that I know anything about that sort of thing. A dropper works very well for this, and the tincture dries in seconds. Its easy to dry layer upon layer to build up the potency to "unreal" levels, so I've read. I also read (or dreamt, I don't recall) that a dropper and a 15ml bottle of concentrated ToC is an instant "joint-o-matic" that will keep a party going all night (assuming it's that kind of party, and a supply of cigarrettes - hand rolled are best). 1 ounce of high quality bud will produce about 90 ml of tincture, and it will lasts longer than you would think (high potency, and high efficiency smoking in a pipe or vapourizer = lasts long time!)
I should also say, that I first started using n-hexane for the soxhlet extractions, then diethyl ether. Then I started the extractions with alcohol, removed the alcohol, then extracted with ether. A fair amount of time, work, and odours! I found it to be unnecessary.
I have never used chloroform, so I can't comment about that. (I mean for the soxhlet extractions...)
My experience based on the solvents I've used indicates that THERE IS NO SUBSTITUTE FOR ACTIVATED CARBON. No lab should be without activated carbon, it really cleans up the tincture good. IT REMOVES ALL OF THE CHLOROPHYLL. Solvent juggling to get the active ingredients without extracting any chlorophyll is very difficult. Butane is dangerous. I have done the butane extraction, but it can be difficult to get a good extraction. Could you imagine extracting with butane for several hours? Activated carbon is cheap and widely available. If you are interested in producing cannabis tincture - get the carbon. I still have some of the cannabis oil left, I could post a picture if anyone wants to see.
The final light yellow oil could then be worked to isolate the THC, but I have never carried that out.

PainKilla, those pictures about THC acetate are text from the book entitled "Marijuana Alchemy", by D.Gold.
It's an interesting little book.

[Edited on 9-2-2005 by CycloKnight]
BASF
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painkilla: i rather think the sodium-salt of thc-cooh will dissolve in aqueous phase.....no decarboxylation just by adjusting pH to pH9. Wether it helps decarboxylate at lower temperatures? ..... i guess that if you have the thc-cooh in aqueous solution(in which it is much more soluble than in organic sovents), it would even be more stable at pH 8-9 (stronger solvatitsation).
Maybe high excess of NaOH would help? - >>pH 10.

Of course it seems interesting.....you wouldnt need vacuum or inertgase-equipment for decarboxylation.

[Edited on 9-2-2005 by BASF]
trilobite
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The carboxylic acid derivatives are decarboxylated very easily by heating the plant material. I think it was 15 minutes at 120 degrees centigrade but this is from top of my head. Yes, this has been verified also in the scientific literature. Did you know that alcoholic KOH is a reagent for testing THC because of decomposition with formation of color? No need to make things harder than they are. The most selective solvent for the extraction are aliphatic hydrocarbons, but I question how effective the brief cold liquid butane treatment actually can be. One thing is sure: it is FAR from being supercritical. It's a plain crude liquid extraction. Check out the critical temperature and pressure for butane if you don't believe me. Soxhlet with hexane or bp 60-80C pet ether would of course be different in regards of effectiveness. The acetyl-THC thing is an urban legend, it has been discussed and debated throughly in the past.

Oh how threads like this make me wish the Hive was up again... Interesting to read about the ethanol and active charcoal though, but I'm quite sure it will also mean some losses.
JohnWW
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Cycloknight talks of using 95% ethanol as the solvent for cannabis oil. Because 95% ethanol carries a very high excise tax/duty in most countries, it is quite expensive, unless you can distil your own from materials like sugar, whey, sugary fruits, or starch. It is likely to be cheaper in many places to buy substitutes like methanol, propanol, isopropanol (the 68% azeotrope sold as "rubbing alcohol" is probably not good enough, though), tert-butanol (forms a 65% azeotrope); or else acetone. Most other otherwise suitable solvents are not completely miscible with water, or they form an azeotrope which is over half water. Whatever is used could, in theory, be distilled off afterwards, although contaminated by water in the case of those that form azeotropes. Of course, "denatured alcohol" or "methylated spirits", sold in supermarkets as a cleaning agent or fuel, being ethanol adulterated with methanol, a blue dye, and other substances such as pyridine or sucrose acetate to make it unpalatable, is much cheaper, but the contaminants may be undesirable for solvent extraction.

[Edited on 10-2-2005 by JohnWW]

[Edited on 10-2-2005 by JohnWW]
prole
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easy THC extraction

I have dreamt many times of extracting THC from cannabis using solvents, mostly alcohols. Every time I was left with pleasant tasting and potent oil, containing lots of extraneous oils. It's messy and time-consuming, but I learned a great deal. Then I came across a method using butane (erowid.com). When I thought really hard about this, I found that one can perform an extraction in about 30 minutes, from setup to completion. There is no large volume of 'undesirable' oil present, and like what was mentioned earlier in this thread, it is in the 90% THC range. When I dreamt of this method, I was using one-year-old-stored-in-a-paperbag-in-the-basement leaf material. The resulting oil was, as mentioned earlier in this thread, incapacitating. I dreamt of smoking it in the Badlands of South Dakota, and found great difficulty in walking the 5 feet or so to my tent. Acetylating this product or even isomerizing it is almost pointless, as the effect is so powerful. But I shall dream of it nevertheless. The only drawback I see is the evapourating butane and it's effect on the environment. One cannot simply collect it and reuse it. Obvious advantages are low solvent amounts (liters are not required), speed and ease, and powerful amotivational syndrome-producing material. This MUST be done outdoors, away (far, far away) from sources of ignition. Hope this helps.

[Edited on 4-8-2005 by prole]
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 Sciencemadness Discussion Board » Fundamentals » Organic Chemistry » possibility for THC extraction Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication   » References Non-chemistry   » Forum Matters   » Legal and Societal Issues   » Whimsy   » Detritus   » The Moderators' Lounge