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Rate of THC Decomposition to CBN

SkyHighLer

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The results indicate complete conversion of THCA-A/D9-THC. The sum of the molar concentration of THCA-A and D9-THC decreased slightly after the decarboxylation, the relative loss is given in Table 1. Figure 4 also shows the data for CBN, which is a possible oxidation product of D9-THC. In this case, heating in the dark and in the absence of oxygen (vacuum oven) did not result in any significant oxidation of D9-THC to CBN. Finally, decarboxylation studies with pure THCA-A showed clearly that D9-THC was the only decomposition product observed after heating at 110°C for 40 min.

https://online.liebertpub.com/doi/pdfplus/10.1089/can.2016.0020

I attached a screenshot of Table 1 mentioned in the above quote.

Another statement from the paper,

The decarboxylation reaction for THCA-A was essentially stoichiometric with no side reactions. In particular, no CBN (a common oxidation by-product) was observed under the experimental conditions.



Another paper,

Decarboxylation of Δ 9-tetrahydrocannabinol: Kinetics and molecular modeling

https://www.researchgate.net/public...drocannabinol_Kinetics_and_molecular_modeling


2.1. Materials
Methanol was HPLC grade and was purchased from J.T. Baker (Deventer, The Netherlands). Medical grade cannabis plant mate- rial (female flower-tops) was obtained from Bureau Medicinale Cannabis (The Hague, The Netherlands). It had a D9-THCA content of about 18%, and virtually no free D9-THC. The water content was 3.6%. The standards of D9-THC (4.2 mg mL 1 in methanol – ref number 130-151205x) and D9-THCA (1.0 mg mL 1 – ref number 380-250407), with purity higher than 98%, were kindly donated by PRISNA B.V.

2.2. Method
A sample of around 400 mg cannabis was blended in a mixer, and heated at different temperatures in vacuum conditions for a certain time. The temperature range studied was from 90 to 140 °C. To follow the reaction rate, a sample was taken every 5 min for the first hour and then every half an hour until the conversion of D9-THCA to D9-THC was complete. Each solid sample was extracted with 50 mL methanol and sonicated for 15 min before being analysed with HPLC. In a series of extraction experiments it was determined that the extraction process was essentially complete. Calibration lines were determined for both D9-THCA and D9-THC. By this method the solid samples were inherently corrected for weight loss (up to 30% at 140 °C) during thermal treatment. Balances during the experiments, based on the molalities of D9-THCA and D9-THC, are >95%, indicating that the decarboxylation process itself proceeds with 100% selectivity. Some skeletal rearrangements however cannot be excluded.
 

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Ringodoggie

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Premium user
420giveaway
If I may step in and stir the nest a little. LMAO

Here is an article that shows CBN content increasing while THC is still increasing during decarb.

It sounds to me like no one knows. LOL

Shouldn't be that tough of an experiment for someone with the proper equipment and knowledge. Whatever you have to measure content of cannabinoids. I doubt TLC would be accurate enough so it might have to be HPLC.

Set a few common variables and run the tests on flowers, dry sift and concentrate.

If I had an HPLC setup, I would certainly be willing.

Anyway, here is the article that tosses yet another wrench on the gears...

https://marijuanagrowershq.com/decarboxylating-cannabis-turning-thca-into-thc/

About half way down the test reports show the CBN increasing from 0.4 to 1.4% while during the same period the THC was going from 3.8 to 25.5%.

Isn't that contrary to everything else discussed here that says CBN rises only when THC stops converting.

Or, maybe I don't understand. I wouldn't be surprised given all the confusion and controversy. LOL
 

Gray Wolf

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The identity of the breakdown byproducts of the various cannabinoids is a very good question, it is the presentation I took umbrage to.

As previously noted, arguing opinions is counter productive, so instead I e-mailed my favorite molecular biologist, and asked him for his read and any links he might share.

To RD's point, if CBN is going up at the same time THC is, ostensibly something else decomposes into CBN as well.

I also asked what CBD decomposes into, noting how close it is to the THC molecule.

I will start a thread on that subject when I hear back, and post a link here.

Here is a picture of the more common cannabinoids in Wiki. Look at how close the molecules and their cycled molecules are.

https://en.wikipedia.org/wiki/Cannabinoid
 
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Ringodoggie

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Premium user
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Thanks, GW. However (and unfortunately) we don't know how credible or accurate the info I pointed you to is.

It's all a lot of hodge podge in a new and breaking world. Cannabis may be thousands of years old but we sure don't know crap about it. LOL And, now that big money is involve.... people want answers. REAL answers. Not some stoner's opinion based on his personal (and non-scientific) experiences.

So, the first question that comes to my mind is.... how does one obtain a cannabinoid profile from cannabis?

It would be great if TLC would work. I am getting ready to set up a DIY TLC setup but I am having my doubts about the accuracy. I have not looked into a HPLC setup or what it cost but...... if that's what it takes, fine. GW, you have a ball park on what a HPLC setup would cost?

Once an apparatus to read the profile is established and stabilized, the tests would need to be run over and over, changing independent variables like strain. I'm just guessing here but I'll bet that a high THC/low CBD strain will react very differently than a high CBD/Low THC strain.

Also, I'm sure, flowers, sift and rosin will also require very different procedures.

Fortunately, once the testing apparatus is in place, analyzing the data would be cheap and fairly easy. More of a data collection and presentation than anything.

This is certainly not outside the scope of my abilities so I'll start looking into it. It may be outside my cost range if the HPLC setup is a lot of money.

I did see a really cool handheld cannabis analyzer that was perfect. Pop a small sample into the cup and in minutes, you have a full cannabinoid and terpene profile. After reading about it, it was bull shit. It was called MyDX or something like that.
 

SkyHighLer

Got me a stone bad Mana
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The identity of the breakdown byproducts of the various cannabinoids is a very good question, it is the presentation I took umbrage to.

As previously noted, arguing opinions is counter productive, so instead I e-mailed my favorite molecular biologist, and asked him for his read and any links he might share.

To RD's point, if CBN is going up at the same time THC is, ostensibly something else decomposes into CBN as well.

I also asked what CBD decomposes into, noting how close it is to the THC molecule.

I will start a thread on that subject when I hear back, and post a link here.

Here is a picture of the more common cannabinoids in Wiki. Look at how close the molecules and their cycled molecules are.

https://en.wikipedia.org/wiki/Cannabinoid


https://en.wikipedia.org/wiki/Cannabinol#cite_note-13

Unlike other cannabinoids, CBN does not stem from cannabigerol (CBG). There is no clinical evidence that THC breaks down naturally into CBN once the THC has become decarboxylated and forms delta-9 THC. CBN is formed by decarboxylation of CBNA.[13]



[13] Medical Jane, Cannabinol CBN

https://www.medicaljane.com/2013/08/19/cannabinol-cbn-will-put-you-to-bed/


As is the case in many of the known cannabinoids, cannabinol (CBN) stems from cannabigerolic acid (CBGA) in cannabis. The plant naturally produces enzymes (aka synthases) that convert the CBGA to one of 3 major cannabinoids: cannabichromene carboxylic acid (CBCA), cannabidiol carboxylic acid (CBDA), and tetrahydrocannabinol carboxylic acid (THCA).

When the plant develops THCA, it usually will be converted to THC as a result of heat or UV light. That being said, THCA can be converted to CBNA over time as well. Prolonged exposure to air causes the THCA to lose hydrogen molecules and oxidize; now we have CBNA. Just like the rest of the acidic cannabinoids, CBNA will convert to cannabinol (CBN) when exposed to heat or UV light.
 

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Ringodoggie

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"When the plant develops THCA, it usually will be converted to THC as a result of heat or UV light"

This quote was from the medicaljane site. Am I to understand that I can decarb my cannabis by using UV light and no heat? How long and what type of exposure? I may have some old HIUV lights from curing stations or something else laying around.

I know cannabis will naturally decarb under normal UV light over time. But, it's a long time. Not minutes. I wonder how much a high intensity exposure to UV would speed up the process.

I have been decarb'ing my canna for 40+ years the same way every time. In the oven... 240F for 40 min. Probably read it in an Ask Ed in a 1970's High Times mag and never changed my method. LOL

Time to find out for sure... the proper way.
 

Ringodoggie

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Premium user
420giveaway
OMG!!! Un-fucking-believable. The devices that are available for cannabis analysis are everywhere. I guess I should have known. Money brings out all the big dogs.

I guess the days of wrapping heating pads around glass columns and comparing color charts is way behind us. LMAO Agilent makes some unbelievable cannabis analysis tools. The software is all written and the learning curve to operate looks VERY minimal.

I ordered this one and they assured me I would have delivery before Christmas. I'm pretty excited.

https://www.aimanalytical.com/Cannabinoids.html



HP6890.jpg
 

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G.O. Joe

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Here is an article that shows CBN content increasing while THC is still increasing during decarb.

Would anyone like to guess what the THCA is showing?

This quote was from the medicaljane site. Am I to understand that I can decarb my cannabis by using UV light and no heat?

No. Not the most credible source. There is only partial understanding, like in catscientific's 70% statement. What both of Dussy's graphs show is a rapid decline in THC and THCA with increasing temperature, in his vials that are not everyone's vials. THC to CBN is kind of established. THCA to CBNA unless the temp and time precludes this. It is understood that there should be intermediate dihydrocannabinol and dihydrocannabinolic acid and two of each.

There will be added necessary costs to actually use your GC. It may take a few minutes to read the manual.
 

Ringodoggie

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Premium user
420giveaway
There will be added necessary costs to actually use your GC. It may take a few minutes to read the manual.

Good thing I can read. LOL I taught myself how to use a focused ion beam microscope to optically read a secure microchip that I decapsulated (when I reverse engineered XM Radio's security) with nothing more than the manual so, this shouldn't be too tough.

And, when I did that I had to break into the lab at night after everyone went home and teach myself with nothing but the manual. Here, I have all you helpful people to help walk me though it.

Piece of cake.

EDIT: After reading my post it reads a little pompous. LOL Wasn't meant to be. ;)
 
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WaterFarmFan

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Veteran
OMG!!! Un-fucking-believable. The devices that are available for cannabis analysis are everywhere. I guess I should have known. Money brings out all the big dogs.

I guess the days of wrapping heating pads around glass columns and comparing color charts is way behind us. LMAO Agilent makes some unbelievable cannabis analysis tools. The software is all written and the learning curve to operate looks VERY minimal.

I ordered this one and they assured me I would have delivery before Christmas. I'm pretty excited.

https://www.aimanalytical.com/Cannabinoids.html

Dude, I seriously like your style!!! Head first into the deep-end!!! I am very envious in fact. Did you get a 5890 or 6890 system? What options? How much???
 

Ringodoggie

Well-known member
Premium user
420giveaway
I wish. Sorry, but I have to call bull shit on myself. LOL I didn't even ask for a quote but my guess is probably close to 50k for that GC unit. LOL Sorry but that's outside my price range for a new toy. LOL

Actually, I'm looking more at FT-IR spectroscopy for personal use. Unfortunately, the FTIR can only provide a partial cannabanoid profile. About half of what we can get from GC or HPLC. So, for determining the content of 'trace' cannabinoids, (as discussed in this thread) the FT-IR will not be sufficient. However, for my personal use in determining the 4 or 5 major cannabinoids, the FT-IR will do just fine. At about 1/10th the cost of the GC unit that I would LOVE to have. LOL
 

WaterFarmFan

Active member
Veteran
Ok, now you HAVE to get a quote, just so I can know!!! Haha I was hoping someone was refurbing this tech just for the canna industry at affordable prices. I was thinking more along the lines of $10k for an older 5890 system with basic warranty and support.

https://www.ebay.com/itm/HP-AGILENT...ON-DATA-SYS-W-7673B-AUTO-SAMPLER/132433499910

https://www.ebay.com/itm/HP-5890-Se...tt-Pac-with-FID-and-MS-detectors/112333885567

http://stores.ebay.com/Baseline-Scientific/HPLC-/_i.html?_fsub=11377117012
 

superglue

Member
off the cuff here, butt....
i have tested on my gc many samples of distillate,some pretty sloppy with high heat/crappy vacuum and others with fresh oil in the pump and sub 50 micron readings.
while observing the test results, rarely will the cbn increase
it seems to me the delta 9 will convert to a steadier state delta8 if over...cooked,heated,decarbed,etc
and.. to get a conversion to cbn? i think that will take time more then any other environmental condition
 

PDX Dopesmoker

Active member
Ok, now you HAVE to get a quote, just so I can know!!! Haha I was hoping someone was refurbing this tech just for the canna industry at affordable prices. I was thinking more along the lines of $10k for an older 5890 system with basic warranty and support.

https://www.ebay.com/itm/HP-AGILENT...ON-DATA-SYS-W-7673B-AUTO-SAMPLER/132433499910

https://www.ebay.com/itm/HP-5890-Se...tt-Pac-with-FID-and-MS-detectors/112333885567

https://stores.ebay.com/Baseline-Scientific/HPLC-/_i.html?_fsub=11377117012

The local university had a pretty complete HPLC system for sale last spring used in the $10k range.
 

G.O. Joe

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Veteran
A university HPLC can be very cheap and basic. If it was like a 1100 with software someone should have jumped on it. Go-dove has been mentioned as the source of most of these used systems on ebay, from big pharma such as Merck shutdowns.

I was thinking more along the lines of $10k for an older 5890 system with basic warranty and support.

That's just the beginning though. The oven, detector, controller, and autosampler part is worth about $500 unless you can find a lot of sales for more. A first generation Chemstation CD and win95 computer might cost very little if you can find them. Free OpenChrom might work with a controller on modern computers but there are still connectivity issues. Ringodoggie's next generation of GC might be the better choice.
 

Gray Wolf

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The local university had a pretty complete HPLC system for sale last spring used in the $10k range.

Sadly, that is just a start, as you need a MS following the HPLC to positively identify the molecules.

There is more than one compound that elutes at the same rate.
 

Gray Wolf

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The local university had a pretty complete HPLC system for sale last spring used in the $10k range.

Caveat emptor! I first bought a used Perkins Elmer GC for $1200, and found it no longer served with parts or service, and a used SRI for $12,500 which we still have.

An HLPC would be a handy thing, but vet it closely at that price and consider that to really know what you are doing you also need a MS, so should plan to budget $100K or more for the combo.
 

WaterFarmFan

Active member
Veteran
Damn, you guys love to crush hope and dreams... Haha So, it seems the software is the most expensive part. Interesting in a fucked up patent kinda way...
 
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