Hi All,

So today my grandpa sat me down in his lap on his rocking chair and told me that he had received 300 mg of Gaboxadol HCl. (Don't ask why a thirty year old man gets rocked by his grandfather).



Anyway, Gaboxadol HCl is a derivative of Muscamol, the main psychoactive constituent in the iconic Amanita Muscaria mushroom. It is a hallucinogen/hypnotic and is purported to be significantly more efficacious and safer as a hypnotic than existing alternatives. (My man Hamilton Morris did an excellent show about it btw if you're interested in the history: Hamilton Morris: A fungal fairy tale

In any case, as grandpa was rocking me on his knee, he suddenly bend down to me with a sad face and told me that he was worried because the sample he had received was only about 90% pure. He was able to determine that most of the sample did, in fact, contain Gaboxadol, but he couldn't identify the contaminants.

Being a good grandson, I decided to help my grandpa, and figure out how to purify his sample for him to remove any potentially toxic contaminants (such as ibotenic acid). I scoured the literature, but my search proved fruitless however, but then I remembered that the Nexus is frequented by many a talented alchemist who would know how to approach my grandpa's dilemma.

If this is you, then I would be very grateful for any procedures for purifying Gaboxadol (or even just Muscamol) that you are aware of. I am eager to learn anything you might know. I would also be grateful for any references for books or papers that describe techniques for doing such purifications.

Any advice is greatly appreciated!

Cheers, Albert

Hi AlbertChemist.

Is there any particular reason why you would want to remove Gaboxadol HCl? It doesn't seem to be (very) toxic as it has been used to treat schizophrenia.

Hi PsillyPsymons,

I'm interested in removing the impurities from the Gaboxadol HCl sample in order obtain as pure of a sample as possible, because I'm interested in doing some spectroscopy on it, and because grandpa want to use it to help him sleep.

I'm also not sure about Gaboxadol being an antipsychotic. (Do you have a reference for that?)

In fact, as far as I'm aware, in can even act as a psychotogen/deliriant when co-administered with amphetamine type drugs.

Holy crap wow! I think this is something I'm going to just start researching all on its own for personal benefit, I'm fascinated tell your grandpa that and make sure you're good to him

FIRST we probably need to identify and figure out how to identify the impurities. We will probably need someone really knowledgable on TLC and chemistry to chime in they will ultimately have more to say other than "holy crap wow" and "we need to find someone with more knowledge on this" lol

Super fascinating: I think we'd need to gather reductionary information and deduce things we are certain aren't if that makes sense because once we clear out the questions we don't wanna ask about this... once we boil it down to just the solution.. grandpappy will have his day then

Might also consider too; as we learn more about the questions we're asking to not forget there might still be somewhere on the Nexus where pertainent information resides... don't flinch with our search engine, we could probably type in key terms and deduce out the posts with the least relevance and when that doesn't pan out we have to consider other options for looking to finding our solution.. like outside of dmtnexus

I doubt TLC is going to be helpful, mass spec at the very least. If you're worried about wt% of completely unknown, potentially neurotoxic contaminants in recreational drugs, maybe you should just throw them away. At least with natural products you have a better idea of what to expect. I doubt it even makes sense to go through the steps to correctly identify impurities, remove them, then verify the purity of less than half a gram of street grade drugs that you know very little about. Depends how concerned and risk averse you are I guess.

A vivid fantasy about grandpa, huh? Brings me back to the SWIM style fantasies about people's cats doing drugs.

Anyways, if this was a question of optimizing the ratio of muscimol:ibotenic acid in extracts of amanitas (to a certain point), there are published solutions for that. But this really does not seem relevant to your situation.

P.S. I'm not an alchemist or chemist

Hi Albert, AM very interested in this molecule too, I never had the opportunity to come accross it. Tell your grandpa he's a lucky duck.
Its a good alternative to muscimol, but I imagine it is pharmagrade as I do'nt see why it wouldn't be. I'm wondering what are the possible 10% impurities and it they are to worry at all. I mean, could be just quality but not a risk ? Not sure beside GC/MS analysis, other technic you could do and I have no idea how you can purify it further even, but you'll need someone with good chemistry background ( or the chemist badge here ), someone like Benzyme, Mindlusion or AcaciaConfusedYah could maybe answer.

Thanks for all the helpful input.

Looks like I first have to figure out what exactly the impurities are. I only have some very basic equipment to do this. Ideally, if we can find the proper solvent, I think a recrystallization might be a good approach. Another possibility would also be using a chromatography column, but again, I would have to know what to pack the column with.
Maybe the best thing to do would be to send a small sample to a lab that has a GCMS in order to identify the impurities.

Are there any rules of thump for finding a suitable solvent for recrystallization? It would have to be something that dissolves the Gaboxadol at high temperatures but not a low temperatures.

Also, depending on the contaminants, a simple liquid liquid extraction may even work.

Grandpa's gonna sleep like a baby

There are two basic ways of doing recrystallization. You just outlined one. The magic one we hope for, a solvent that its insoluble in in the cold and reasonably soluble in when hot. That's like mescaline sulfate in water or DMT in heptane. If you are lucky either methanol, ethanol, or isopropanol will do it in this case.
The other option is dual solvent recrystallization. In that your primary solvent still holds on to too much of the compound in the cold but, when its hot, you add a solvent its less soluble in until the first little crystals form, and then you cool it.
For example, if you tried the strongest isopropanol you can get and added just enough solvent to dissolve the compound when hot and you only got half to crystallize out overnight in an ice bath you could heat it back up, adding enough isopropanol to dissolve it at 55°C, then add some acetone and slowly cool the mix to 0° and keep it there overnight.
Be sure to not heat the initial solvent above the boiling point of the second solvent. It helps to warm up the second solvent before mixing, of course.
With good solvent choice your impurity will either be filtered out when the solution is hot or it will remain dissolved when the mixture has crystallized.

As to the choices of solvent, that is an issue of the polarity of the target of your recrystallization. Here you have something full of nitrogens and oxygens and its the hydrochloride salt, so quite polar. That's why I'd expect lower alcohols [or even water] to be the primary solvent and something just a little less polar like acetone being a secondary solvent, if needed. For instance, mescaline hydrochloride can be washed with cold acetone or recrystallized with isopropanol.

Don't breathe the fumes from things like hot methanol and acetone.
Remember, medical and industrial ethanol can contain bittering agents.
Keep notes, don't throw anything away until you're done.

@AlbertChemist
By which analytic method was that 90 % purity determined?

Thank you Elrik for the detailed info for the dual solvent recrystallization! I'll study this more to see how it can work here.

Also, according to Grandpa, the Gaboxadol.HCl is actually 95% pure, not 90%. Since then, the IR spectrum of Grandpa's sample was checked against a sample of 99% purity. Below are the spectra (95% is from Grandpa). I also included the spectrum of Ibotenic acid, just to show that the sample is not this nasty little compound.

I am a spectrum analysis enthusiast, my question is the following. I see the same number of peaks in the 95% sample as in the 99% sample spectrum. Am I to assume that the difference in amplitude in the second half of the spectrum is proof enough that there is a contaminant? Is there a possible contaminant that will still only show the same number of peaks, but interfere with the amplitude?

Or to phrase it differently, if one were to recrystallize pure Gaboxadol HCl, and only leave a sample of the contaminant in the IR analysis medium, will it be an entirely different looking spectrum in IR?

If I am missing an overlap, please highlight where it happens, it is either my tired eyes or bad image quality. Thanks!

Sodium chloride would fulfill this requirement, as would any other alkali metal halide. That might not have been what you were thinking, though!

That said, there does seem to be something pushing up the absorbance but without any distinct peaks both between 4000 and 3000 cm-1, and between 2500 and 1500 cm-1. In both these ranges the absorbance for the 95% purity sample is greater than that for the 99%. The lack of distinct peaks suggests that it's a mixture of random crud rather than a single compound. Looking closely, there's a similar difference at around 700 to ~400 cm-1.

Finding out the precise synthesis route that was used would give insight on the likely contaminants present.

I don't know what the contaminants are at this point, but the 99% sample does seem to have an additional small peak at around 3500. That being said, this peak might just be obscured by noise in the less pure sample. I'm hoping to eventually do some chromatography on it to hopefully be able to get more insight on the purity and contaminants.

That's typical for a water OH stretch.