Stability of Lysergamides in Absolute Ethanol Solution?

[Mercurious]

Greetings, fellow travelers!

I apologize if I'm posting this in the wrong place, and I've scoured the archives here at BL in an attempt to avoid asking a totally redundant question, but I have yet to discover a satisfactory answer to the query I pose in my posts' title.

Specifically, I'm looking at the possibility of making a liquid solution out of AL-LAD and I'd like it to remain as stable as possible for longish-term storage--inasmuch as said solution CAN be stabilized. To this end I've been considering different solvents that might suffice, and it seems as though absolute ethanol (aka, 99.5% undenatured anhydrous ethanol USP) might work, but I'd really like to get some feedback from some of the more technically inclined and experienced voices here before I take the plunge.

Basically, my question is this: am I correct in thinking that an absolute ethanol solution of AL-LAD--kept in sealed glass vials in a freezer--will be significantly more stable than a similar solution using 95% ethanol (e.g., Everclear)?

If not, what solvent or approach would anyone recommend instead (besides obviously keeping the material as the dry tartarate salt)?

Or, am I just faced with the fact that NO solution (or solvent) will provide me with increased stability for a prospective solution of AL-LAD?

Thanks in advance for any and all feedback, and happy trails to everyone!

 

[Solipsis]

I think because ethanol is also a polar solvent, it will still ionize your lysergamide - and in that ionized form it can more easily react / degrade via intermediate states. Maybe ethanol is slightly better than water but IMO theoretically it's not magically loads better so that the 5% water in everclear would matter.

Personally I plan on making ethanolic solution of AL-LAD just like you but I will be using 96% ethanol, and just make small batches of liquid, leaving the rest as crystal in portions ready to be turned into liquid. Of course all of that will go into my freezer in amber glass.
If the shelflife of my first batch of liquid turns out to be terrible I will just dose blotters or sugarcubes or whatever with any liquid I make next.

I'd like to forward this question with added bonus to more knowledgeable chemists: what about making a DMSO solution? DMSO is not protic and I have some... of course it solidifies / 'freezes' even in a fridge so if you are willing to accept having to wait a little bit before enough of the solution thaws to make a drop come out of your dropper, the upside is that in frozen state shelflife should be even better since there is less molecular movement. Superior right? (while not tasty)

 

[.:Holy::Toast:.]

You have crystal AL-LAD?
PEGS! SHOCKS! LUCKYYYYY

 

[Thomas Davie]

I'd like to forward this question with added bonus to more knowledgeable chemists: what about making a DMSO solution? DMSO is not protic and I have some... of course it solidifies / 'freezes' even in a fridge so if you are willing to accept having to wait a little bit before enough of the solution thaws to make a drop come out of your dropper, the upside is that in frozen state shelflife should be even better since there is less molecular movement. Superior right? (while not tasty)

Ask, and I shall tell Sir (I work with DMSO about twice a week).

Couple of things about DMSO. It's nasty stuff as far as health issues go, but I gather you're talking about small quantities. We go though maybe 1 litre every few months. It's got the unique property that if you spill it on your skin you'll be able to taste it inside of 20-30 minutes. It just magically goes through skin. I use nitrile gloves when I handle it.

As a phenomenally good solvent, you might even find that you can transdermally dose yourself. And yes, it will solidify when you put it in the freezer, so make sure you *very* thoroughly mix it after thawing out in order that your solution becomes homogenous again. Don't want any surprises.

I honestly don't see why LSD wouldn't be stable frozen in DMSO, but then I wouldn't have a problem with storing LSD in 100% ethanol if you can get a cold enough freezer, but I assume you're talking about a home freezer @ -20C?

If you have the capability to weigh out 1 mg that wouldn't be an unreasonable test.

Good luck.

Tom

Wanted to add that Sigma Aldrich sells 1 mg/ml standards of LSD in Acetonitile (to researchers with a license), and that's another polar aprotic solvent. The LSD is stable in acetonitrile at room temperature, so freezing would be even less likely to harm it.

 

[psood0nym]

You have crystal AL-LAD?
PEGS! SHOCKS! LUCKYYYYY

You and the OP don't need AL-LAD crystal to do this. If you simply soaked some blotters in a small quantity of distilled water for a bit and dumped it out to evaporate then you'd have crystals too.

Like Solipsis, I'd leave the AL-LAD as separate crystal quantities and only turn it to liquid when I planned to be using it soon. To make the dry crystal doses you'd simply need to do a liquid extraction of the blotters and mete out the doses by volume with a syringe into separate tiny containers/media, which you'd then gently evaporate the AL-LAD/liquid solution from. Being typically less than one milligram, the amount of a single crystal dose in such a context would be difficult to see, so do be fastidious about labeling if you try it. Keep your volumes low and try a single trial dose this way to make sure everything works the way it ought to in theory.

 

[Thomas Davie]

You and the OP don't need AL-LAD crystal to do this. If you simply soaked some blotters in a small quantity of distilled water for a bit and dumped it out to evaporate then you'd have crystals too.

Like Solipsis, I'd leave the AL-LAD as separate crystal quantities and only turn it to liquid when I planned to be using it soon. To make the dry crystal doses you'd simply need to do a liquid extraction of the blotters and mete out the doses by volume with a syringe into separate tiny containers/media, which you'd then gently evaporate the AL-LAD/liquid solution from. Being typically less than one milligram, the amount of a single crystal dose in such a context would be difficult to see, so do be fastidious about labeling if you try it. Keep your volumes low and try a single trial dose this way to make sure everything works the way it ought to in theory.

There is specialized equipment used to evaporate very small volumes of liquid; and typically this is done on 1-2 ml conical vials using gentle streams of inert gas (e.g. nitrogen). Chemistry like this is beyond most people though. I'm assuming Solipsis obtained crystal Al-Lad and didn't generate it from blotters, although I could be wrong.

But if you've got blotter that you know/trust there'd have to be a good reason to go to the trouble of extracting it from the blotter to crystallize.

Tom

 

[Mercurious]

Thank you, Solipsis, Thomas, psood0nym, for your input on this. Much appreciated!

Also, my apologies for leaving this thread hanging the past week. I'm a grad student and teacher this semester, and I've been running a bit ragged lately. Finally have a few minutes to pursue my other research interests (if not a few hours to actually DO the research!).

At any rate, I'll certainly be taking everything y'all have suggested into account when I make up a solution at some point, I'm just not sure when that'll be yet. Plus, I don't have much material to work with--at all--and I'd like to make it count in the best way. That being said, it's not going to be possible for me to keep breaking up little bits of my small stash to make fresh solution out of when needed. Plus, if it's only to be made into solution when it's needed, then why actually make up a batch of solution at all? Que no?

So, while absolute ethanol is still a polar solvent, my thought was that if the solution was immediately divided up into a few smaller vials (say 1 mg ea.) which then were quickly frozen (albeit in a consumer-grade freezer, but set as cold as possible) this might help keep the solution relatively stable for quite a bit longer. My understanding that this would help, however, was based on the presumption that even a small percentage of water in the ethanol (even the 95-6% azeotrope) would expose the lysergamide to a much greater degree of potential oxidation in solution than it would in dehydrated EtOH. From what y'all have said, however, this wouldn't seem to present much concern.

DMSO is also something I have immediate access to, and never would have thought to use until reading the above. How much (or little) DMSO is it safe to ingest? (I know that it's used in alternative medicine practices for various purposes--internally and externally--but I'm not sure how or how much is used.) Also, as a side note, I have in fact applied a LSD/DMSO solution topically, many moons ago, and it does indeed work. (I think I first got the idea when I was but a wee lad--or maybe when I was 16 yo--reading about how Kessey and the Pranksters considered mixing a bunch of acid into DMSO so they could paint it all over the seats, railings, and surfaces of the Cow Palace [a huge concert venue south of San Francisco] for a big festival they were planning to hold there. Had they done so, in theory anyone who touched a surface that had been coated with the mixture would have LSD immediately carrier through their skin and into their bloodstream by the DMSO...)

Oh yeah, almost forgot to add, I also have Diethyl ether immediately available which I could theoretically use as a solvent, que no? It's a non-polar solvent too, if I recall. Nonetheless, it seems like it might be a tricky--and altogether volatile--carrier to work with, but I'm totally game if it is a viable route. So, on that note, does anyone know if there would be any major advantages or disadvantages to using ether a primary solvent for long-term storage of a lysergamide solution?

 

[chantarr]

it should be okay but id keep it out of light, light is very destructive to LSD and other compounds

 

[Mercurious]

^^^ Yes, indeed, light is very destructive to LSD--one of the worst things, in fact. Direct sunlight will destroy LSD almost instantly. Light, moisture, and heat (but, as the tartarate salts, they should be stable in any surface temperature found on earth)--in descending order--seem to be the biggest concerns. Also, chlorine is obviously another thing to avoid at all costs, so of course one must never use tap water around lysergamides either.

 

[Boognish]

I know this is old, but I didn't want to start a new thread. So, what became of the al-lad/ethanol solution? Is 95% everclear a good solvent to use with lysergamides or will it cause degradation? Thanks