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Old 02-25-2010, 01:36 AM #1
dope_roor
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Question What is/how to perform decarboxylation & isomerization?

I'm trying to figure out exactly how decarboxylation and isomerization of THC occurs and what methods can be employed to do so.

I have some some background organic chemistry knowledge and understand that decarboxylation of marijuana is the conversion of THCA into THC, THCA being psychoinactive whereas THC is. On a molecular level, it's the removal of a COOH group from the THC molecule, which can be done under conditions of high heat or presence of a strong base.

I've read that perhaps the process of curing buds is actually a slow decarboxylation process and thus the increasing of potency we generally observe.

Based on this, it's reasonable to assume that applying heat increases the potency of marijuana. And there's evidence of this in making cannabutter from schwag or whipping up BHO over heat or the heat pressing of kief into hash. some sort of increase in potency from the original product.

Is it not then also plausible that washing or soaking the bud in an alkaline (basic pH >7) should also cause decarboxylation? Perhaps a more thorough decarboxylation than whipping over heat? And, as long as the solution is polar, the THC should not be affected?

The implications of this are perhaps washing our buds in an alkaline solution before performing our preferred method of extraction could increase the end potency of the extract?


Onto isomerization, I understand that it is the rearrangement of the molecule structure. What causes THC to isomerize? I believe the cannabis alchemy articles and other info from the 70's use a strong acid to cause the isomerization. First of, is there any truth in this?Can other methods cause such isomerization?


Just trying to clear things up, it seems that some people confuse the two, and I'm thinking that these are two distinct processes that can occur/be performed to increase potency
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Old 02-26-2010, 02:02 AM #2
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I can answer the decarboxylation question. I just recently got through reading a patent for extracting cannabinoids from cannabis using CO2 extraction, and the first step after drying, before they do anything else, is a decarboxylation step. They performed experiments to find the most efficient temp/time and found:

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Therefore laboratory studies demonstrate the optimum conditions for the decarboxylation of: Chemovar producing primarily THC to minimise CBN formation, is 1 to 2 hours at 105° C. or 1 hour at 120° C.
This took into account that the heat used to convert the THCA to THC will also cause the THC already present in the sample to degrade into CBN, and they found the best temp/time under both considerations. They also say that as the size of the batch increases, the temp/time would also need to be increased, due to uneven heating of the material in the oven.

Now, it is true that over time THCA will convert to THC naturally. The curing process will actually increase potency, but it's real advantage comes from allowing the other plant products to break down like chlorophyll, etc..., that give the smoke a harsh taste. This is because most people decarboxylate the THCA when they smoke or cook it, with the heat from the fire/flame to light/cook it. This is not as efficient as cooking it in an oven at a known temperature for a known time for maximum conversion, but it does the job well enough that most people would never know the difference.
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Old 02-27-2010, 10:04 AM #3
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the way I understand it is:

1) DECARBOXYLATION: removing carbon dioxide from THC-A to convert it to (biologically active) THC,...this is done with heat, either buy burning, like in a pipe, joint, bong etc,..., or by heating in an oven, or in a lipid such as butter or oil (I hear coconut oil rocks), with the oven/butter methods intended for ingestion.

2) ISOMERIZATION: in the plant CBN degrades into THC-A, which dries, and loses carbon dioxide, then becomes THC (as above) and then further degrades into CBD (if I got it backwards someone will correct me, I'm rather medicated) if your plant has a LOT of CBN, you can "FAKE" the degradation by adding a strong acid (I used hydrochloric when I did it) in a reflux setup with a solvent, this adds a double bond on the benzene ring or something like that, and makes a molecule that is an isomer of THC (great explanation, huh?), so you end up with almost no CBN, because it's now converted into THC-isomer, which WILL get you baked, because your body cant tell the difference between it and THC,.........the trouble with this is most weed in the last 30 years has very little CBN even when picked early, so isomerization will work AWESOME if you have a field of kentucky ditch weed (wild hemp, considered a nuisance, grows all over the state), but not so great on your "crap I got mites, I have to harvest 25 days early" northern lights super dank,.......but it will increase the potency of the extracted oil, by the factor of how much CBN was available when you did the reflux/isomerization.

for the record, I never put the extracted "honey oil" back on the buds, I just mixed it with some dry sift to make what we called "putty", but is now referred to as jelly hash.

I hope that answered your question,.......you can read "marijuana chemistry" by michael starks, he has a whole section on isomerization, pretty well written, and is where I learned about the process WAY back in the late seventies


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Old 02-28-2010, 07:11 PM #4
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Quote:
Originally Posted by dope_roor View Post
I'm trying to figure out exactly how decarboxylation and isomerization of THC occurs and what methods can be employed to do so.

I have some some background organic chemistry knowledge and understand that decarboxylation of marijuana is the conversion of THCA into THC, THCA being psychoinactive whereas THC is. On a molecular level, it's the removal of a COOH group from the THC molecule, which can be done under conditions of high heat or presence of a strong base.

I've read that perhaps the process of curing buds is actually a slow decarboxylation process and thus the increasing of potency we generally observe.

Based on this, it's reasonable to assume that applying heat increases the potency of marijuana. And there's evidence of this in making cannabutter from schwag or whipping up BHO over heat or the heat pressing of kief into hash. some sort of increase in potency from the original product.

Is it not then also plausible that washing or soaking the bud in an alkaline (basic pH >7) should also cause decarboxylation? Perhaps a more thorough decarboxylation than whipping over heat? And, as long as the solution is non polar, the THC should not be affected?

The implications of this are perhaps washing our buds in an alkaline solution before performing our preferred method of extraction could increase the end potency of the extract?


Onto isomerization, I understand that it is the rearrangement of the molecule structure. What causes THC to isomerize? I believe the cannabis alchemy articles and other info from the 70's use a strong acid to cause the isomerization. First of, is there any truth in this?Can other methods cause such isomerization?


Just trying to clear things up, it seems that some people confuse the two, and I'm thinking that these are two distinct processes that can occur/be performed to increase potency

I typically decarboxylate the extractions for oral application in a hot oil bath at 250F for ~30 minutes.

We ran an isomerization experiment using sulfuric acid to isomerize the BHO in an ethanol suspension and ammonia to neutralize it.

We then added hexane to steal away the cannabinoids from the alcohol, separated them using a separatory funnel, flashed off the hexane, and voile!

Sadly our ability to make stuff has progressed faster than our fractional separation and measuring project, so we don't know what we did, other than four of us lab rats did an unofficial test by vaporizing some and smearing a couple of raw papers, which I rolled some Blueberry in.

Even sadder, all four of us testing are high tolerance patients who no longer experience euphoric highs and though all of us noticed it over our background medication, and three out of four of us experienced it as headier than the base Shiskaberry/Blackberry oil before isomerizing it, none of us were blown away.

The 6'7" 250# ostensibly lowest tolerance member of the group was the dissenter, and said that it seemed about the same but gave him a mild headache.

I did note that while I noted the enhanced head effect, typical of elevated THC, I didn't experience any speedy or bruxing effect, which usually accompany high THC for me.

Due to the absence of some of the high THC symptoms that I usually experience, I also wonder if the isomerization process itself didn't finish the evolutionary cycle of cannabinoids not only from CBD to THC, but also from THC to CBN in some cases.

Higher CBN to accompany the higher THC would explain the absence of speed and bruxing due to its sedative effect.

More info on the subject after we get volunteer test panel results back, which include a range of medical conditions and tolerances.

My impression so far is that it works just like the books say, but Shiskaberry and Blackberry are not high CBD strains, so the effect was not earth shaking.

We have acquired a high CBD medicinal strain that we will re-run the experiment on when we harvest her babies.

We are also continuing to plod along with our actual empirical measuring experiments so we have more than just subjective and anecdotal test data. More then, when I actually know what I am talking about.

GW
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Last edited by Gray Wolf; 04-12-2011 at 09:31 PM.. Reason: Update time and temperature
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Old 05-16-2010, 03:49 AM #5
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I have already posted the best available decarboxylation articles; time now for the isomerization articles.

Obtaining Δ9 THC by isomerization looks to be out of reach for most.

The procedure using sulfuric or tosic acid was shown to convert CBD (or Δ9 THC) to only the less active Δ8 THC. Using HCl instead gives a mixture and a very low yield of Δ9 THC.

CBD and BF3.Et2O, or hydrochlorination of Δ8 THC with Lucas-type reagent/dehydrochlorination with NaH, gives a THC mixture greater in Δ9 THC. Using potassium t-pentoxide for dehydrochlorination gives better yields of Δ9 THC.

https://ifile.it/nar2wzm

Δ8 THC is reported to be a more effective anti-emetic.
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Old 05-16-2010, 04:35 AM #6
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The straight skinny is, forget isomerization, big work, minimal if any resulting improvement, I did a mess of it decades ago. And converting with a liquid is messy, with potential residue implications, and not needed, heating it works the trick easily, with little mess or cost.

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Old 05-16-2010, 08:21 AM #7
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Quote:
Originally Posted by Haps View Post
The straight skinny is, forget isomerization, big work, minimal if any resulting improvement, I did a mess of it decades ago. And converting with a liquid is messy, with potential residue implications, and not needed, heating it works the trick easily, with little mess or cost.

There are many paths, not all lead to doors worth opening.
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Old 05-16-2010, 08:50 AM #8
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Quote:
Originally Posted by reckon View Post
the way I understand it is:


2) ISOMERIZATION: in the plant CBN degrades into THC-A, which dries, and loses carbon dioxide, then becomes THC (as above) and then further degrades into CBD (if I got it backwards someone will correct me, I'm rather medicated)
Wrong, it is conversion of CBD to THC.
Which in general is a complete waste of time as western drug types have almost zero CBD to start with.
As for decarboxylation you do not need to do it unless you plan to eat the Cannabis. Smoking, even vaporization converts almost all the THCA to THC.
-SamS
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Old 05-16-2010, 09:00 PM #9
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Old 05-17-2010, 06:53 AM #10
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This is old info that has been proven to be wrong. THC comes from CBG not CBD, CBD also come from CBG, each different Cannabinoid has its own synthase that converts CBG to the end Cannabinoids.
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