We’re in SoCal but could probably get a sample up there
2 Likes
Same with me. In SD but I may be able to get it dropped off by our distro as they are in sac regularly.
1 Like
It’s more of a hunch, I don’t know, really. I know that it’s reported that it’s really hard to carboxylate THC with MMC, while it works quite well with CBD.
That reaction probably involves a fully developed charge on the carboxylate at some point, maybe that’s a reason why even Mechoulam’s group couldn’t get it to work, maybe it doesn’t wanna stay on the resorcinol ring of THC?
I did find one patent related to this so I am probably wrong:
Cool I will be in touch as soon as I know.
First reported here:
Present in 0.5% and authors suggest Biochemical Variation and Chemotaxonomy.
4 Likes
Nice find thanks for posting this!
1 Like
Excellent paper. I have been trying to get the CIF file from that paper but don’t have access to the databases yet. I have the CIF for the THCA-A and made some nice pictures and videos of the structure in the chalking diamonds feed. I will do the same for THCA-B when I get the data.
There are no coordinates associated with that paper. That was just isolation, IR, melting point, conversion to other structures.
Coordinates are in here:
http://actachemscand.org/doi/10.3891/acta.chem.scand.29b-0379
2 Likes
Right! That is the paper I was actually thinking about. Now I will have to read the other one you posted. I could write a CIF file from this paper but I am too lazy. I am sure I can find the cif to put into mercury and get the pictures I want.
So theoretically if the medusa stones were the result of a reactive crystallization and we’re actually a salt what piece of analytical equipment would be able to see the difference? The more I think about it the more possible it seems as they crash out so far before super saturation and they have other strange properties.
@DocKnott @moronnabis
2 Likes
It’s hard to say, I would tend to say crystallography XRD because best case scenario XRD would probably tell us everything we need. But XRD will not give any info at all if the structure is not clean. Meaning if there are disorders in the structure which there would likely be if the crystal chalked up. We could try powder XRD which could give us some clues but not as good as single crystal. If that doesn’t work we would likely need multiple types of analysis like NMR, along with HPLC and GC/MS.
1 Like
there is an entire US patent on the production
of various salts of cannabinoic acids.
the hplc solvents are acidic (eg methanol formic)…they will disassociate the salt and protonate it.
The HPLC mass spec has identified dimers…small amounts at
2x mol weight and eluting late.
5 Likes
To second @DocKnott , the best way to figure this out is with a multitude of different instrumentation. The more analyses, the better. In addition to XRD and NMR, I’d wager time-lapse SEM would be of great use here.
4 Likes
I like SEM. Man if only I could afford the lab I dream of…
1 Like
Would humic acids be able to bind to THCa?
If you look closely at the THCA molecule…you will notice the
COOH and Ortho OH on the benzene ring. With out the rest of the THCA this molecule alone is salicylic Acid. There are hundreds of studies of “binding” of salicylic acid , intramolecular and intermolecular
studies. These studies provide an ideal model for THCA in solution. Your question concerns intermolecular bonding to organic acids. The answer is yes, but the type of bonding and the complexity
of resulting forms, is very much dependent on pH, concentration, and whether the bonding studies are done in hydrophilic solvents like water and alcohols, with and with out inorganic ions present, or in Hydrophobic
solvents like Hexane.
The salicylcic acid portion of the THCA can bind numerous inorganic ions, organic acids, organic amines, organin amides…it seems endless the number of intermolecular forms as well as 3-4 intramolecular forms.
This coupled with the fact that over 4000 organic chemicals have been identified in the capitate heads of stalked trichomes from marijuana makes the total number of possible interactions rather difficult to predict.
If you look at the partial list of the most abundant organics found in
capitate heads, (posted as a reference in “Butane works but no theory”)
you will see that one fatty acid amide, palmitamide predominates on
a mole basis. So if you are wondering what might fit the in situ binding
molecule…that is certainly a good candidate. However, the THCA protonated also is capable of binding to itself in concentrated solutions to form dimers.
What ever exists in the trichome capitate head…
a good deal of THCA protonated form…seems to appear after solution in
Butane, including the protonated dimer.
So when we talk about THCA complexed with itself or other molecules
we have to distinquish between whether we are talking about in situ
in the trichome head…VS…what is going on in butane or alkane solutions
which we concentrate to create a “mother liquid” from which crystals form.
regards,
4 Likes
I know this is somewhat off-topic but there’s actually a paper on a covalently bound THC dimer, its molecular weight being double minus two water molecules:
Free PDF available for anyone interested.
6 Likes
I agree with @mitokid about both the accidental incorporation of an acidic impurity and also that you won’t see it in a typical CoA. Depending on the degree of the impurity, the tightness of your UPLC/HPLC calibration curves, and the dilution ratio during sample prep, you could potentially elucidate this, but it wouldn’t be a cake walk. NMR or some crystallography technique would be better.
1 Like
Do you think GCMS would be able to show different THCA-M (M = metal) salts via slightly different mass peaks for the positive ion in the salt?