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acetonitrile as 1-P-LSD soln.

Incunabula

Incunabula

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A very well-known vendor, with a very good reputation (understatement of the year :) ) is selling 1-P-LSD dissolved in acetonitrile. I have two questions in that regard.

First, according to him: "The solvent used is acetonitrile to increase the stability of 1P-LSD in solution", I assume this is true (because this vendor really is a pro :) ) But I'm just wondering what would be the idea, or chemistry, behind that?

Second, I assume it's safe for ingestion, because he wouldn't be selling it if it weren't. But I have some 1-P-LSD powder myself, and was considering using acetonitrile as solvent. Thing is, according to C.L.P acetonitrile is classified as:

Flam. Liq. 2 H225
Acute Tox. 4 * H302
Acute Tox. 4 * H312
Eye Irrit. 2 H319
Acute Tox. 4 * H332

http://echa.europa.eu/da/information-on-chemicals/cl-inventory-database/-/cl-inventory/view-notification-summary/9535

That's not something I would ingest even a single drop off. So, what do you guys think? Would it be a mistake of me to get some to make my 1-P-LSD soln.
 
Everything is toxic; dose determines poison. You are right to worry about the toxicity of acetonitrile however.
https://en.wikipedia.org/wiki/Acetonitrile

The wikipedia link above displays a table showing the toxicities of different nitriles in rats. Potassium cyanide is the most toxic at 10mg/kg. I know you can't scale this up to humans, BUT, the toxic dosage of KCN in humans is 200-300mg, and this could vary even more depending on the stomach aciditiy (more acidity > more hydrolysis to HCN). This suggests multiplying by 20 would give a good human toxicity estimate. Acetonitrile toxicity is at 2500mg/kg in rats, so we can take a fair guess that the human LD50 will be around 50 grams of the stuff.

But, just to be very very safe I recommend consuming less than 1 gram of acetonitrile for every dose. Since the density of acetonitrile is 0.786g/ml, if you keep under 1ml per dose, it is fair to say that you will be under toxic dosages. This stuff is used a lot in organic chemistry, eg it is used as the solvent in taking LC-MS samples, and so people do inevitably inhale small amounts over the course of the day. Just use as little as possible, 1ml or less is good.

The reason why I think acetonitrile would stabilise 1P-LSD is because it is not really basic at all. In water, the 2 labile protons can come off and add back to the wrong side of the molecule (to give an inactive isomer). This is less likely to happen in a non-basic solvent like acetonitrile.

Just wait till a few more people confirm that my suggestions are safe before doing anything though.
 
Acetonitrile is smelly stuff, I don't think it would be pleasant to ingest. Honestly I wouldn't ingest it in any amounts, ever. You'd have to be insane to willingly ingest anywhere near a gram of this stuff.

It might make a good storage solvent as you have suggested. Also, it's quite volatile so one could just lay it onto some substrate a day or so before ingestion and let it evaporate.
 
Acetonitrile has the lowest toxicity of simple nitriles because of its extremely slow metabolism to give the cyanide anion, and it is true that ingesting 1 gram of it would probably be completely ok. However, even so I personally wouldn't feel comfortable purposefully ingesting cyanide, even in minute quantities, but that is not really based on any objective information. Does anyone know the chronic effects of ultra low cyanide poisoning? Anyway, because it is a lysergamide, I assume you won't be taking that every day, so from a once-a-month indulgence I doubt there would be any significant health effects.

I have worked with acetonitrile and honestly the smell is alright, all things considered. There are FAR worse smelling solvents. Don't know anything about the taste though. Anyone also think the smell is similar to acetone for some reason? The only unpleasant side effect from (sometimes purposefully) inhaling some acetonitrile I experienced is the faint smell of it on my breath for the next 10 hours or so. Much like you can smell acetone on your breath after smelling/drinking it (or isopropanol).

And aced has a good explanation for the increase in stability, but are lysergamides sold as enantiopure compounds or racemates? Anyway acetonitrile is regarded as an aprotic solvent, so proton transfer is unlikely to occur. Do you mean the protons of alpha carbons of the N,N-diethyl amide group and the one next to the tert amine? Well, those have negligible acidity as is, but yeah I guess acetonitrile would increase the stability... Then again I don't see why it has to be acetonitrile, acetone is about as aprotic as the former and significantly less toxic, and I'd think that 1P-LSD would have acceptable solubility in it.
 
Nah I mean the protons on the chiral carbons, and I think they are sold as chiral because they are synthed from lysergic acid. A complete synthesis would probably be too costly.
 
Polar/dipole aprotic solvents (dmf, dmso acn,) are excellent for dissolving compounds in a water free environment (aprotic), this can lead to increased stability time, extend shelf half life.

However dmf, acn do undergo hydrolysis readily, yet, acn solutions when ingested at less than 1mL concentration are probably not that harmful.

Z
 
aced126 said:
Nah I mean the protons on the chiral carbons, and I think they are sold as chiral because they are synthed from lysergic acid. A complete synthesis would probably be too costly.
Click to expand...

Well the carbons I listed are the chiral carbons. Anyway, that's a good point, I didn't think about the fact that they probably use lysergic acid. Total synthesis would make no sense.
 
Thank y'all, for your answers. It's appreciated.

Very interesting about acetone. I do wonder why said vendor went with acetonitrile, if acetone is just as aprotic. Obviously people aren't going to be ingesting more than a coupple of drops maximum in one session. But the less toxic alternative should still be preferable.

If nobody else has someting negative to say about the idea, I might try using acetone as soln. I'm sure 1-P-LSD is plenty soluble in it, I mean, there's really no reason it shouldn't be, right? It deters bacterial growth. It's not really toxic and doesn't taste too bad (if it tastes like it smells :) ). Also, it's cheap and easily available.

I'll report back when I get to it. I could imagine this thread would be of interest to a lot of people, lysergamide powder being so easily available atm. Hhmmm, now just to find someplace were I can borrow a laboratory mcg scale to measure out those 2 mg for the bottle.
 
Yeah, I think you should test how acetone works on a small scale and report back. If it does, there's really no need for acetonitrile, not as far as I can see anyway. Then again thinking about this, maybe they went with acetonitrile because it's pretty good at dissolving salts and organics of all kinds of polarity alike and your 1P-LSD may be as a salt, in which case acetone will probably not work. But do try and report back, I'm getting curious.
 
Some news..

I wrote the vendor, and this is the answer I got:
"We chose acetonitrile as the paper below shows it reduces the rate of epimerisation of ergopeptines compared to other solvents. I don't believe they mentioned acetone but that might be a possibility. I don't know how soluble 1P-LSD would be in acetone, sorry."

Here's the link to the study: http://www.ncbi.nlm.nih.gov/pubmed/12078743

My 1-P-LSD is the tartrate salt, btw. Still not sure if I'll risk some of it, putting it in acetone. I mean, I know I'll just evaporate the acetone off if it doesn't work, but I'm no chemist :) And to be honest acetonitrile is pretty cheap too, actually.
 
A small amount of acetonitrile (less than 5mL) is non toxic. It's metabolized to acetic acid, comparatively much less toxic than other nitriles, I think the LD50 is something like 2.5 grams/kg?

You can evaporate it on gentle heat or a watch glass and redissolve the salt in distilled water or ethanol if you are concerned about it.
 
sekio said:
A small amount of acetonitrile (less than 5mL) is non toxic. It's metabolized to acetic acid, comparatively much less toxic than other nitriles, I think the LD50 is something like 2.5 grams/kg?

You can evaporate it on gentle heat or a watch glass and redissolve the salt in distilled water or ethanol if you are concerned about it.
Click to expand...

Metabolized into acetic acid? I was under the impression that it was metabolized into hydrogen cyanide, albeit very-very slowly, which is the reason for its comparatively low toxicity. Looking at Wiki it says that it actually results in the production of formaldehyde and hydrogen cyanide. I mean it makes sense that it could be metabolized to acetic acid, but can you source that please?
 
Why don't you go for 70%+ ethanol and store your vial in the freezer so that it's safe from bacterial growth , evaporation and the 1p should readily dissolve in a dH2O and ethanol solution ? Also this would allow for blotting if you so wished to make a couple doses out say for a night to take throughout the night and save you having to carry the vial ?
 
Seph. Alcohol isn't aprotic. The point is that acetonitrile is going to prolong the stability of 1-P-LSD, if you're going to keep it in liquid for long time.
 
The molecule doesn't have to be aprotic, just non-basic. I can't see any problems with alcohol tbh.
 
Hmm, in that case it would be a problem as water definitely does isomerise it into inactive isomers over time...
 
Did some further thinking and decided to check what experimental data has to say about the basicities of these solvents. Turns out that ACN isn't that much less basic than water, neither is acetone. I had suspected that. Then again I wonder how they measured DN of water, methanol etc since they are supposed to react with SbCl5 instead of forming a complex.

Another thing though is that ACN has a significantly lower dielectric constant, so that further suppresses potential ionization too. Anyway I'm really not sure if this is all relevant considering the ridiculously weak acidity of C-H acids. If it was up to me, then I would store the drug in an acidified ethanol/water solution and be done with it. As far as I can see, there's no sensible reason to use ACN. Might as well use nitromethane then.

If you're planning on storing the drug for a really long time, then store it as a solid in an inert atmosphere. Pure nitrogen works too, doesn't have to be argon.
 
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