Sharing my Research

[squiggly]

So the fact that the carbolic acid molecule has 3.5 out of its desired 4 bonds is the reason why it's acidic, right?

I should also clarify this.

If you count them up--there are still actually 4 bonds. It's just that they are not 4 stable bonds. They are 3 full bonds, and two half bonds (which are weaker). We can do reactions on this functional group in this state because it wants to stabilize itself more.

In fact, the conversion of THC-a to THC (decarboxylation) is exactly such a reaction. It turns out that if the carboxylate anion just craps off that CO2 on the end, the CO2 can take that instability with it (and actually increase the overall stability of the system). If you think of it this is entropically favored. In the above reaction a hydrogen takes the place of the CO2 group, and the parent molecule becomes neutral.

This frees up the central carbon atom to make a 2nd bond to the negative oxygen. Now everyone's happy, and there is no charge on either molecule.

 

[Cyclol]

o_O wait... just a minute... :confused: what I would like to say it's... :eek: I have no doubt that Weed Chemistry is your passion goal Squiggly !!!
I think I would need above average quality medication to be able to read this entire thread and may be understand at least 5 or maybe 20% of what you explain depending on THC % of my meds !!

That said, you really seem to be a crazy straight up biochemist, and must recognize that the information shared should satisfy more than one, and probably me too when I will find the appropriate medication to help me absorb all this information...:):):)
And finally this post would remain of little interest were it not to wish you good luck for this Friday, same if I'm pretty sure your research efforts leave only a small room for luck !! ;) o_O

So, Peace and Good Luck anyway !!!

 

[Dunge]

It's like teaching an old dog algebra.

 

[urbanite420]

I should also clarify this.

If you count them up--there are still actually 4 bonds. It's just that they are not 4 stable bonds. They are 3 full bonds, and two half bonds (which are weaker). We can do reactions on this functional group in this state because it wants to stabilize itself more.

In fact, the conversion of THC-a to THC (decarboxylation) is exactly such a reaction. It turns out that if the carboxylate anion just craps off that CO2 on the end, the CO2 can take that instability with it (and actually increase the overall stability of the system). If you think of it this is entropically favored. In the above reaction a hydrogen takes the place of the CO2 group, and the parent molecule becomes neutral.

This frees up the central carbon atom to make a 2nd bond to the negative oxygen. Now everyone's happy, and there is no charge on either molecule.

Danm Squiggly, you're taking me back to my undergrad days!! Mad respect for ya! That's some great work you're doin there!

Isn't the "unstable" bond just an ionic bond versus the "stable" covalent bonding? Also is stability in this sense meaning that the molecules have found their state in which they are the most "grounded." We should start a convo about pK values and their contribution to acid/base reactions. If I rembember correctly, the bigger the pK the stronger the dissociation? lol I always hated the henderson-hasselbach, but I later learned to appreciate it.

 

[squiggly]

pH = pKa + log [A-]/[HA]


tiny Ka = small dissociation

yup.

As for the bond--nope we consider it a unstable covalent bond still.

For the type of "unstable bond" you're talking about--look at something like diethyl zinc. This has the part covalent part ionic bond character (and as a result it's explosive in air).

 

[ttystikk]

So to ask a different chemistry related question; we're all aware that you can't smoke or otherwise ingest fresh green wet buds and expect to get high. Yet, not only does it have the desired effect once it dries(assuming of course that it has enough of the requisite cannabinoids!), but it retains that effect even when cooked into things, and is presumably wetted again in the process. Why?

 

[aldus]

This reminds me why I went for chemical engineering instead of chemistry.

Cool work.

 

[ttystikk]

This reminds me why I went for chemical engineering instead of chemistry.

Cool work.

Ooooo- do tell! I'm interested to hear what spice your expertise might bring to our fair table, laden with the bounty of knowlege...

 

[squiggly]

The hydration isn't the issue when we're drying it necessarily. Its more the protective effect of water against heating. The decarboxylation effect (loss of a CO2 molecule) is what renders the substance active. High water content can complicate this when smoking, there are a few things to consider--boiling point depression, the effect where water can form a protective layer of gas around something (lick your finger, touch an iron--no burn). In effect when we smoke we are still vaporizing THC, most of the compound that directly burns or touches fire is destroyed. The water makes the transition from not hot enough to fire too fast to vaporize/decarboxylate THC-a effectively.

 

[ttystikk]

The hydration isn't the issue when we're drying it necessarily. Its more the protective effect of water against heating. The decarboxylation effect (loss of a CO2 molecule) is what renders the substance active. High water content can complicate this when smoking, there are a few things to consider--boiling point depression, the effect where water can form a protective layer of gas around something (lick your finger, touch an iron--no burn). In effect when we smoke we are still vaporizing THC, most of the compound that directly burns or touches fire is destroyed. The water makes the transition from not hot enough to fire too fast to vaporize/decarboxylate THC-a effectively.

So this explains why vaporizing without combustion is more efficient.

Does the fact that THC likes to mix with fats have anything to do with this? I'm still a little lost why it works in food.

 

[aldus]

Ooooo- do tell! I'm interested to hear what spice your expertise might bring to our fair table, laden with the bounty of knowlege...

Not much unfortunately, I barely know any chemistry. I took ochem and didn't do well, my thermo focused pchem class was more entertaining.

I just take the stuff from the chemists and size it up. Squiggly is dropping knowledge for sure.

 

[squiggly]

Does the fact that THC likes to mix with fats have anything to do with this? I'm still a little lost why it works in food.

It works in food because you're eating it. You're not to cook canna-treats beyond the heat of vaporization of THC, else you'll vaporize it away--however, yes fats and such as well as viscosity of what its being cooked in can trap the THC inside a brownie or something. This is no different from how BHO needs to be heated in order to purge correctly--without heating, the oleoresin is too thick to release the butane.

These are called inclusion impurities (pockets of impurity trapped in a viscous liquid or crystal structure).

Okay I think I just understood your question:

You're asking how is it active when we cook it (beginning wet), and we dry it--but not when it's just wet.

The answer you're looking for is heat. Heat is necessary to decarboxylate the THC-a and form THC. THC-a is non psychoactive--it is also water soluble and will not cross the blood-brain barrier easily.

When you add the requisite heat--even if the stuff is still wet--the decarboxylation will move forward, this is a heat dependent process (and requires slightly alkaline conditions such that the COOH group is deprotonated to yield COO- (which I've drawn earlier on).

The main reason you won't get high if you just eat this stuff straight (we already discussed smoking it wet) is that it will drop into your stomach acid. In this acid the THC-a will be in its protonated form. The earliest it could begin to decarboxylate (which would be possible at body temps) would be upon entering the intestines, which are slightly alkaline. However, conditions in the stomach and on the way to the intestine are very rough. This stuff is a chemical soup which is designed not to let anything pass unscathed.

My guess is that any THC-A making its way into the stomach will be degraded significantly. The most obvious point of attack on the molecule to my eyes would be the cyclic ether in THC-a (the ring which is held together by an oxygen atom). These break down in strong acids.

Whatever makes it past your stomach will have bile salts and other such things to deal with before being absorbed.

The long and short of it is that when you haven't dried it, or applied heat in the correct way--you're not ingesting the correct substance.

Upon drying, you'll end up with probably 60-40 or 70-30 THC:THC-a. Ratios could be more favored to THC, haven't really checked out the kinetics on this reaction (if they've even been studied for this molecule). The full weight of the THC is released when it is hit by the hot air which is heated by the embers burning above it. Again as I said before any THC that is actually touching the embers is being destroyed. Think of smoking a bowl as forced-air vaporization, except its the burning weed which is providing the heating element.

This reaction is happening in the bowl/chamber and on the way into your lungs once the compound is heated enough.

 

[ttystikk]

Not much unfortunately, I barely know any chemistry. I took ochem and didn't do well, my thermo focused pchem class was more entertaining.

I just take the stuff from the chemists and size it up. Squiggly is dropping knowledge for sure.

And 'sizing it up' is a valuable skill in its own right, says this frustrated mechanical engineer. Anytime you have something to say, consider me a ready audience.

 

[ttystikk]

Okay, so this explains why drying your product until its completely crispy- without ever getting it hot, of course- makes it work better in both vape and food. Easy enough to do around here; damn humidity falls into the single digits on a regular basis! Also, isn't baking soda alkaline? Bet that's why it helps make brownies so potent... On the other side, adding it to spaghetti sauce probably won't be as good, because of the natural acidity in tomatoes. Or do you think it would make a difference?

Stomach acid is hydrochloric acid, a strong acid, right? Is that acid interaction the reason why eating it is relatively inefficient? I always thought it had more to do with the time factor; it takes so long to get into your system and build up in the bloodstream that you need more just to feel it. And of course it lasts longer than a toke, too.

My favorite vaping tool I have found thus far is my buddy's temperature controlled heat gun! I just twist that dial to about 450, put it down on the pipe and inhale slooowwwwly... I have a nice vaporizer but I like the heat gun better, it seems to work better and I get a better taste from it, most likely from the fact that I'm getting very close to the ignition point. Gonna have to get me one of those... lol

 

[squiggly]

Okay, so this explains why drying your product until its completely crispy- without ever getting it hot, of course- makes it work better in both vape and food. Easy enough to do around here; damn humidity falls into the single digits on a regular basis! Also, isn't baking soda alkaline? Bet that's why it helps make brownies so potent... On the other side, adding it to spaghetti sauce probably won't be as good, because of the natural acidity in tomatoes. Or do you think it would make a difference?

Stomach acid is hydrochloric acid, a strong acid, right? Is that acid interaction the reason why eating it is relatively inefficient? I always thought it had more to do with the time factor; it takes so long to get into your system and build up in the bloodstream that you need more just to feel it. And of course it lasts longer than a toke, too.

My favorite vaping tool I have found thus far is my buddy's temperature controlled heat gun! I just twist that dial to about 450, put it down on the pipe and inhale slooowwwwly... I have a nice vaporizer but I like the heat gun better, it seems to work better and I get a better taste from it, most likely from the fact that I'm getting very close to the ignition point. Gonna have to get me one of those... lol

Tomato sauce wouldn't make a difference if you decarboxylated your material first.

As far as eating it, yes--it could very well be that it's not getting in your system until it hits the intestine. I'm looking at that alkene and that ether as possible points that may become charged in acid (to cross a membrane a compound usually becomes neutral, this is why we have an acid absorption area--stomach--and a base absorption area--intestine). It usually takes awhile to get into the intestine--and even then as I've said the a lot of active ingredients may be totally destroyed in the stomach.

and yes, HCl is a strong acid.

 

[squiggly]

Not much unfortunately, I barely know any chemistry. I took ochem and didn't do well, my thermo focused pchem class was more entertaining.

I just take the stuff from the chemists and size it up. Squiggly is dropping knowledge for sure.

It's funny because I chose chemistry because chemical engineering seemed too difficult (I hate physics and calculus--but I'm good at the latter). Unless I go doctorate, you guys tend to make more money :)

 

[monkeymun]

Wow, have some serious reading to tackle in this thread. Looks like you are in a fascinating line of work.