Carboxylation - Adding the "a" back to THC


#1

Okay I don’t know much about formal chemistry.

If we can decarboxylate our oil, causing the thca to lose its COOH , converting to THC, then could we (in theory) do some magic tricks to go backwards and convert back to thca?


pH balancing THC distillate (quick oxidation/color issues)
Acetone crystallization of THC-A
Decarb oven
#2

sounds like chemistry…seems more like magic.

I know there is an “I’d like to buy a clue” option around here…where is the “ask a chemist” button??

@QGA? @DrPaul?


#3

That’s a tricky one !
https://www.masterorganicchemistry.com/2011/05/20/common-mistakes-with-carbonyls-carboxylic-acids-are-acids/


#4

Sweet! I’ll have to dab a bit more before I can decipher that science jargon. Makes my head hurt…


#5

I could look into this more but the reason the loss of CO2 is so easy to perform from a chemical perspective is because it is a very “favorable” reaction. A very negative delta G in terms of gibbs free energy. Your body does a plethora of these decarboxylation/carboxylation reaction and this energy can be used to either create or consume ATP!

This may help, synthetic reactions for adding on carbon dioxide. Overall be pretty energy intensive and no way around that from what I can see.

https://www.organic-chemistry.org/synthesis/C1C/carboxyls/carboxylations.shtm


#7

wow. that does look like a whole bunch of ways to put the genie back in the bottle.

many of them seem to require starting points that look like synthetic challenges in and of themselves. none jump out at me as a trivial answer to the OP’s question.

I’ve certainly told the boss “nope, not happening” on at least one occasion.

Given that there are so few novel ideas these days, I would assume that if it was easily accomplished we’d have seen it on instagram already.


#8

Yeah, putting the ‘a’ back in THCa is a bitch.


Recrystalizing distillate?
#9

It would be a cool slogan for a consultant tho! Lol


#10

Could try removing any air/water from reaction and use high pressure while bleeding in CO2. Unfortunately or maybe fortunately the decarboxylation is so favorable it makes this step tough!


#11

yes there is a method to add that back to the molecule


#12

@Drjosh is this a trick you perform? Or teach others to perform?

Is it worth the effort? How about the price of admission?

for the crowd: Does the chemical synthesis performed move us from isolating a naturally occurring compound to manufacturing a controlled substance? Or are we there already the moment we add solvent to biomass?


#13

@cyclopath, our industry is on the cusp of greatness. Hydrogenated cannibinoids, are being explored, other varyations as well. The key now for our development of products is the pharmacological understanding of these novel compounds. This is a great time to live and breathe!:tada:


#14

Carboxylating cannabinoids is not the same as hydrogenation. How is that applicable to this conversation?


#15

Enlighten us please sir…


#16

Hmmmm…not how I saw that going down.

I figured you were about to bring cannabosides into the discussion :slight_smile:

which frankly seem like a more useful trick than putting the “a” back.

asked the Google about Hydrogenated cannabinoids. need to share this hit: what is hash oil


#17

I made my remark to this

I know the processes are different, I was elaborating on the recent progress we have made with these molecules. Hydrogenation is an example of transforming a naturally created compound that was isolated into a different form.

Is this manufacturing a controlled substance? Could be, probably, most likely is? That was my answer .


#18

from a chemistry standpoint, saturating those double bonds to slow in-vivo degradation/elimination, combined with added sugar moieties to give water solubility seem like very reasonable tweaks. They also seem like crossing the line into the realm of big pharma as far as regulatory issues go.


#19

hmmmm…420 you say?


#20

and don’t worry about the NDA, I promise we’ll forget it ever happened :slight_smile:


#21

Distillate is a good target to reintroduce the carboxyl group. Especially if all the cannabinoids can be isomerized back into d9 thc before hand.
Yeah?