Prep. of delta-9-thc hemisuccinate (THC-HS)

does anyone have any experience in the esterfication of THC into its various ester analogs/isomers?

I have been doing research on crystalline, water-soluble analogs of our favorite hydrocarbon (thc) and stumbled across this...

"SUMMARY OF THE INVENTION



The present invention comprises an economic procedure and an efficient process for converting THC to its ester. The almost quantitative yield of conversion of THC to its ester distinguishes the present invention from the prior art.

THC can be esterified by reaction with an acid, an acid halide or an acid anhydride in the presence of a 4-aminopyridine either alone or in admixture with an organic amine such as, for example, an organic mono, di or trialkyl amine. The esterified THC can be purified by column chromatography and/or by HPLC."

The fist underlined statement of this summary of the invention abstract from US patent# 6008383 leads me to believe that this esterfied version of THC has existed for quite some time...
The second underlined statement of this summary of the invention abstract leads me to believe that this is a relatively SIMPLE esterfication...

Now for everyone thinking to themselves... SIMPLE!!!! how is that in anyway shape or form simple?!?!? go to another forum and let someone with at least pre-graduate organic chem experience provide USEFUL info on this one.

First off before we indulge into this wonderful patent and its listed examples I would like to state some props and acknowledgement towards its inventors:



Elsohly, Mahmoud A. (Oxford, MS)
Ross, Samir A. (Oxford, MS)
Feng, Shixia (Oxford, MS)


To 1.1 g THC(purity 95%) was added 0.46 g succinic anhydride, 0.66 ml triethylamine, 78 mg 4-dimethylaminopyridine and 20 ml methylene chloride. The reaction mixture was left at room temperature for 3.5 hours. TLC examination showed that all the THC had been converted to THC-HS. The reaction was worked up as follows: the solvent was distilled off and the residue was purified on a silica gel column (50 g silica gel, 3x50 cm in dimensions). Fractions eluted with hexane-ether (9:1) and hexane-ether (8:2) were combined and evaporated to give 1.31 g of THC-HS, 95% purity using HPLC analysis. The total yield of THC-HS was 90.32%.

Now a few questions.
1. Would this reaction be induced under an inert atmosphere and would borosilicate glass be advisable?
2. Would a rescale of this production create rate or RXN mechanism problems?
3. Is it absolutely necessary to HPLC the THC-HS? Or could this step be overlooked in a way similar to that of LSD? Sometimes its better to stick to the 33% purity than to silica column everything twice to produce 98% LSD. In this instance the esterfication of THC is much more efficient than that of the reductive diethylamination of LSA-OH so in theory I would already have an acceptable rate of ~40 to 50% esterfication.... right? lol

anyways will someone please get back to me?!?!? I have ooodles of more examples of this procedure that have all been confirmed and tested in significant labs

 

There are two main things that decide how psychoactive a substance is:
1. its bioavailability 2. its shape and electrical potential when in synapses.

this introduces us to an entire new route of administration as well as changing the molecules' shape and hence its electrical influences throughout the brain. This hemisuccinate analog has a much stronger dipole affinity and therefore is MUCH more soluble in solvents such as water. This dipole affinity also causes a shifting of the molecules leading to a more crystalline lattice.

in laymans terms: if you make thc dissolve easier in water it dissolves into us easier because we are comprised mostly of carbon and water lol

THC-HS is crystal thc that dissolves several thousand times better than THCs insufferably low solubility of ~0.0028mg/ml @ room temp

 

it would make it snortable, IVable, you can put it in water and get extremely high its just way easier to use in my opinion. Its also more useful in transdermal and oral applications e.i. a patch or pill

 

indeed it will lead to a much higher risk of serious tolerance/abuse which in turn stems overdoses, crime, and the splitting of families... BUT hey its going get out someday. We just have to really practice personal responsibility and limits as people with this one

 

lol don't tell anyone but the most peculiar chems can be purchased on ebay

You either need resources or enough knowledge to construct your own precursors from scratch. The great thing about this reaction is that once you have the chemicals it is almost fail proof. All you do is add them and let it sit!

 

@washedmothafuka
you are right GC is not very knowledgeable BUT who is? lol this is patent pending stuff and right now only double or triple doctorates are working on it. So i kinda expect 98% of people to not even know about it. However, its important to bring this to the public's attention and discussion because knowledge is power.

The concentrate was about 98% pure THC, obtained through a hexane extraction, double distillation, and HPLC. Then it is added to the mixture, allowed to react, then HPLC'd again. The 90% is a reference to how efficient the procedure was... They should have obtained about 1.42g but they only obtained 1.31g which happens due to human error. When your boss spends an insane amount of money on your lab, wages, equipment, and precursors they REALLY want to know how much money YOU wasted due to not being perfect. Kinda fucked up if you ask me, I have had to work with $64,000 a gram allotropically labeled HNO3 and it is WAY harder to not spill stuff or lose stuff when you are so nervous (about owing the feds over $130,000 because of a small spill) and shaky someone with epilepsy could do your job better.

 

I also posted this EXACT reaction because I feel it is the only one that could easily be carried out by clandestine chemists. Its a one pot shot, efficient enough that you do not need chromatography, and the chemicals... not too hard to find if you are skilled in diversion and precursor engineering. Kinda like PCP, Somewhat hard to make, impossible to order precursors for, BUT if a rogue chemist was determined enough he could make every single chem needed with just a short drive to a few local stores and a few google searches. (hint hint... Chinese and Indian customs DO NOT search exports ONLY imports wink wink)

 

In this specific procedure 98% pure THC was used however most people speculate that doing the same procedure produces the hemisuccinate salt of most of the other cannabinoids, so its just preference really. Its essentially a matter of sativa high vs indica high you know? The reason why most people don't like the pure THC high is because they become confused and panicky with the psychedelic mindset induced by it. However when this same mindset is introduced with the addition of the body sedation from CBD people are just too inebriated to really care that they can hardly think straight or that a million thoughts are crossing their mind every minute from the THC.

Yes N-hexane (careful slightly carcinogenic/very flammable/acutely toxic) then distill twice. I am not sure if stainless steel would work however I believe a stainless steel distillary could be constructed. The main importance is that most people prefer to vacuum distill it to reduce the chances of burning the oil. I have seen custom stills with water aspirators and slight vacuums to distill alcohol faster... could probably modified and used for essential oils such as hash oil.

|Just be careful using metal and solvents, sometimes they can bleed and strip certain metallic components from alloys which could lead to health problems.