Various inquiries about LSA

[zeekborg]

Greeting fellow Nexians! As of late I have become concerned with the quality of some of the psychedelics floating around of the streets out there, and have decided that id rather not consume things that i do not know with certainty the purity or identity of. This has lead me on the quest to create something that would resemble an acid trip in both content and duration.

As such LSA seems to me to be a good idea despite it not being actual lsd many of the trip reports I have read have been quite positive with a lot of potential for something good there. The main concern i have is that i would not enjoy nausea if at all avoidable. It seems to me that most of the reports that feature nausea are either people who eat MGS straight or do some sort of cold water extraction with maybe a pinch of acid to aid things along. However i noticed that those who took more elaborate measures seemed to enjoy a trip without nausea or some of the other unpleasant effects.

So one to anyone who has more experience are my observations more or less accurate or regardless of extraction method there will likely be a substance that causes undesirable effects. Two i have an idea for an extraction process that I hope will eliminate some of the negative effects experienced when eating the seeds. If there is anyone out there who knows more about the chemistry of this and can offer suggestions to improve this your input would be greatly appreciated.

the general idea is this:
grind some morning glories that hopefully contain (from what I've read) 0.67% of their mass as alkaloids. Grind these seeds up and put them in a soxhlet extractor. Use DCM as solvent and extract for 2 days. This would to remove all the potential junk. next Remove solvent from extractor and replace with fresh DCM. add some ammonia to this DCM until the ph is around 9 allow to extract for another couple of days. From what I understand this DCM should contain your product in free base form. Taking the basic DCM add water acidified to a ph of about 5 with citric acid (or maybe tartaric). Separating the DCM from the water should leave you with a water layer that contains your product in a more stable salt form. You could do this multiple times. Collect the water and evaporate (preferably under vacuum to avoid burning the goodies) to a desired concentration. All of this would be done with attempts to minimize exposure to light.

Now if i can actually manage to do a good job does this mean that 1kg of say MGS could give me a .67% yield of product. If so then (1Kg)(0.0067)(1000g/kg)=6.7 g. From what Ive read LSA is active from around 1-4 mg. This would mean that I have 6700mg and about 3350 doses. Assuming my seeds are of good quality and do actually contain 2/3 of a percent of what I am after. If this is the case i needs far fewer then 1 kg of seeds haha, but this seems like far too much, so I assume i have made a miscalculation

This is already very long and rambly but please tell me your thoughts and opinions. To anyone more experienced with LSA extractions I would love to hear your input about this method and to anyone who has had success with a method similar to this one how was the quality of the product?

 

[dxmroid]

Well 12 grams directly ingested after grinding was about a 7 hour trip with pretty nice euphoria and oevs

I dont think you can extract all of it so if I were you I wouldnt expect .67 of your total

 

[zeekborg]

what is a more accurate yield figure? Im going the route of the soxhlet extractor for the goal of high yields, hopefully so i dont have to work with a huge volume of plant material. I suppose i could use HWBR instead of MGS

as far as the rest of what could be called the procedure, look alright?

 

[dxmroid]

I wish I could help you but ive not tried an extraction on lsa might try the other extraction thread on the first page here

 

[zeekborg]

Well thank you for your input. Unfortunately there has been a hold up in getting some MGS. So i might have to wait a few more weeks to give this a try, but when I get the chance I will hopefully be able to write up a more detailed report along with a bio assay to let you all know how it went.

@dxmroid the extraction thread you speak of is kashs extraction technique? I have perused a few extraction teks and as far as i can tell my method should work to produce a active product. Just hopefully something that will produce a cleaner nausea free effect. Im hoping that by reducing the volume of liquid consumed to a minimum (preferably down to a level were one drop would be an effective dose) as well as doing a defat for the first cycle through the soxhlet should help achieve these ends.

 

[InMotion]

Soxhelet extractor probably is not ideal in this case. Too much heat, light, and air flow. You have a soxhelet that can fit a kg of seeds? Wow. Do you really want to be boiling DCM with ammonia in it? Got a fume-hood?

 

[Kash]

SWIM has extracted HBWR with IPA and then distilled it off leaving only a small fraction to air dry... yielded a very potent product too. I believe you would be able to sox extract LSA with IPA, dispite the common belief that LSA is unstable to heat/air/light... go for it.

I would not recommend exposing Lysergic alks to basic conditions for long periods of time. And there is no way that morning glory seeds would come close to yielding 0.67% LSA, more like 0.02% LSA (Weber and Ma, 1976).

 

[InMotion]

LSA is light sensitive just like LSD is... Just like ergot alkaloids are. It's not the diethylamide that gets changed during the photochemical reaction(to the so called "lumi-LSD"). It's the C9-C10 double bond...

Zur Analytik von Lumi-Mutterkornalkaloiden
M. Pöhm, Microchimica Acta
1955, Volume 43, Issue 5-6, pp 1016-1018

Stoll, A. & Schlientz, W. (1955). Ibid., 38, 585-594.

Hellberg,H (1957). Acta.Chem.Scand., 1, 219-229.

So it's not a "common belief", there's experimental evidence that is well reported. Screw it I'll upload the articles otherwise you'll probably never bother reading it...

I really hope you distilled your IPA under vacuum. Other-wise you epimerized alot of your goodies, and we all know about the activity of stereoisomers right? P.S. it's not very correct to discuss such an extract as LSA, now is it? Sure you knew that though...

Reference:
Technical note: Epimerization of ergopeptine alkaloids in organic and aqueous solvents
D. J. Smith3 and N. W. Shappell
USDA ARS, Biosciences Research Laboratory, Fargo, ND 58105-5674


So you got any science backing ya up on why you should ever recommend someone to boil solutions of ergot alkaloids in light and oxygenated air? Sure it maybe possible, but yield-wise, why bother. Room temperature or frigid cold are known to be sufficient.

Having glass-ware is one thing, knowing when and how to use it is another.

 

[joedirt]

Just because something is photosensitive or heat sensitive does not mean that all the product is immediately lost upon being exposed to light or heat. All chemical reactions are driven by thermodynamics and statistical mechanics. Just like it sometimes takes hours or day's to form a new product it also takes, hours, day's, weeks, months, years for products to fully degrade.

yes LSA's are photo and heat sensitive, but the single best morning glory tea I have made yet was to first boil water and then steep the seeds in the hot water for an hour mixed with garlic. This sat out on my kitchen counter in broad daylight. I assure you if there was any degradation is was minimal.

Peace

 

[jamie]

^why garlic?

 

[InMotion]

Wow joedirt I feel like I stepped into general chemistry again .

If you read the first paper I posted joedirt, which you did not as it had 0 downloads... It states that in the presence of a UV light without air it took 3 hours for 0.75g of lysergic acid to become 0.25g. Sure it was catalyzed by UV light directly but that's a pretty quick photochemical reaction. If you would like kinetic comparisons I will surely make this more clear...

If you actually took the time to read my second paper, I know what a concept right guy posts papers maybe read them? You could see that at 37*C stored in methanol for 69 hours a large amount of the ergoloid had epimerized. Now what do we know about kinetics from a primitive stand-point, well you mention thermodynamics so I assume you're well aware. What's the boiling point of isopropyl alcohol 80* some odd degrees celsius? you do the math given the average time a soxhelet extraction takes.

hint: Arrhenius equation - Wikipedia
What happens to K when we increase T? What kind of relationship is this? Oh yea that's right.

Room temperature or cold temperature without light exposure and minimal oxygen will always be superior when dealing with ergot alkaloids. I can't believe I am even explaining this still...

Edit - I probably should also mention that molecular oxygen is also well known to degrade ergot alkaloids. Can't find a kinetic study about that though aw shucks. Especially in solutions and more so in hot solutions I am sure.

Albert Hofmann "My Problem Child"
LSD is very sensitive to air and light.It is oxidatively destroyed by the oxygen in the air and is transformed into an inactive substance under the influence of light. This must be taken into account during the synthesis and especially during the production of stable,
storable forms of LSD.

Closest I can find.

Sure you can still have some active product, the guy wants to extract a kilogram of seeds and get a good yield. I offered more than good advice.

 

[joedirt]

Sulfer containing compounds (and heat) are known to break up cyanoglycosides...which are believed to be responsible for some of the nasty side effects of LSA containing seeds.

I'm looking for the reference paper now.


Looking back at my notes.

I boiled garlic in a tea pot with distilled water.
I then let the boiling how water cool for 5 minutes before pouring over the seed mixture and then I let it sit out for 2 hours. I drank everything including the seed pulp. It was approximately 400 seeds (which is a light dose with the seeds I had).

The trip was fairly euphoric in nature, never did reach open eye visuals and had to concentrate/meditate pretty hard to get the CEV's going. This was obviously a function of dose.

There reason I noted before that it was my best experience is because prior to that I had made a smoothie with 400 seeds (same pack) and was seriously ill..though did trip and experience solid euphoria for a couple of hours.

The trip intensities of the water/garlic extract was on par, but it lacked most of the body load and didn't have me almost asleep for half the trip.

I actually need to create a thread. I'm growing three large containers of morning glories (using Rising Spirits advice). I also have one of ololiuqui ..though I'm expecting they will be a multi year project with the potential of total failure...they I certainly hope not!

 

[joedirt]

Wow joedirt I feel like I stepped into general chemistry again .

If you read the first paper I posted joedirt, which you did not as it had 0 downloads... It states that in the presence of a UV light without air it took 3 hours for 0.75g of lysergic acid to become 0.25g. Sure it was catalyzed by UV light directly but that's a pretty quick photochemical reaction. If you would like kinetic comparisons I will surely make this more clear...

If you actually took the time to read my second paper, I know what a concept right guy posts papers maybe read them? You could see that at 37*C stored in methanol for 69 hours a large amount of the ergoloid had epimerized. Now what do we know about kinetics from a primitive stand-point, well you mention thermodynamics so I assume you're well aware. What's the boiling point of isopropyl alcohol 80* some odd degrees celsius? you do the math given the average time a soxhelet extraction takes.

Room temperature or cold temperature without light exposure and minimal oxygen will always be superior when dealing with ergot alkaloids. I can't believe I am even explaining this still...

Sure you can still have some active product, the guy wants to extract a kilogram of seeds and get a good yield. I offered more than good advice.

I wasn't trying to be rude...and your advice was not bad at all. You are also correct that I did not download and read the paper. I do however have a PhD in medicinal chemistry and have some clue as to what I'm talking about here. :thumb_up:

3 hours is a VERY short time...and that's why people alway's mention it. But unless you have it sitting directly under a UV light you are not going to get a 75% loss of product in 3 hours.

Again I'm in no way saying that LSA's don't break down in heat in light. They very obviously do. It's just not instantaneous and sometimes it's worth a little lose of product to get a better extraction....

BTW I don't know that working with 3 kilo's is any different if you have the equipment to do it.... in fact in my professional experience large scale extractions/reactions tend to actually go smoother with higher yields...Much less % loss on things like filter paper and reaction vessels...

Peace

 

[joedirt]

Jamie here is the paper I mentioned.

 

[InMotion]

Well then you probably know a lot more chemistry then I do.

I guess if you're going to use a soxhelet purge it with argon or nitrogen and cover it with foil.

 

[joedirt]

Well then you probably know a lot more chemistry then I do.

I guess if you're going to use a soxhelet purge it with argon or nitrogen and cover it with foil.

Well to be perfectly fair I no longer work as a chemist or in drug discovery for that matter at all.
My day's of working at a bench are long past...

I do also agree with the advice you gave here about usign argon and nitrogen though.
I'm guessing you perhaps have more chem knowledge than your letting on 8)

Peace

 

[Kash]

InMotion, I am well aware of the sensitivities of LSD to light, air, and heat and the papers on it. I would also make the arguement that LSA should be equally sensitive to these factors if I didnt have first hand experience working with it myself that says otherwise.

Similar to joedirt's experience, the fact is that I distilled an IPA solution containing LSA from 100 HBWR seeds, and then processed it to a clean and very active crystal resin. Even being subjected to high heat, air, and light for 1-2 hours, the LSA remained very much intact and active. Took half of it and had one of the most profound experiences of my life (w/CEV's+OEV's), the effectiveness was in no way diminished. From this experimental evidence it seems that LSA is relatively stable during short term exposure.

 

[InMotion]

That's all fine and dandy Kash but the articles I posted are all about ergot alkaloids including LSA(the one is quiet specifically geared towards LSA ). So you're experimental 'evidence' doesn't coincide with in-depth studies about these compounds with real evidence. You didn't bother to read the papers either checking by the download numbers... What kind of losses have you measured doing this procedure? None? Sure doesn't sound like evidence to me and evidence isn't necessarily fact either.

Actually if you ask me, from my 'experimental evidence based on nothing but subjective experiences', I've had CEV's and OEV's from 7-10 seeds of HBWR while your distilled product took you 50. You really sure there was no loss? Then again I am pretty sensitive to most psychedelic compounds. Maybe Fact and Evidence shouldn't be based on subjective experience. Hmmm.


Anyways, LSD can withstand boiling temperatures under light and oxygen for a while as well just like LSA, ergotamine, ergovaline, etc. At the cost of yield and optical purity(as stated before). No chemist preparing such a compound would willingly subject it to such unless it was the only way. So yield-wise, it's best not to subject it to these conditions. Which as I have said several times now, is why I wouldn't recommend a soxhelet extraction unless proper precautions are maintained.

Soxhelet extractions don't take 1-2 hours as I'm sure you know. Typically these are left on for about 8-24 hours. With a de-fat step that means, two runs. We're looking at 16-48 hours of heat, air and potentially light exposure. Doesn't sound ideal to me when like I have said a few times now, room temperature and frigid cold are known to work well.

The TEK you wrote for ergot alkaloid extractions is pretty good, no heat, makes sense. Not to say there aren't better less solvent consuming ways. Why not recommend your tek or something similar instead of a soxhelet knowing these short-comings? Unless you're really convinced of your in-depth study of distilling IPA once from an extraction. By the way you shouldn't distill IPA to dry-ness it can form peroxides.

There are so many good ways to perform LSA and ergot alkaloid extractions, a soxhelet filled with DCM and aq. ammonia is not one I would ever consider(does this even make sense to you kash because it really doesn't to me). Testing the pH of DCM with aq. ammonia "in" it? Is that really a procedure, or does the OP not understand very well how pH is measured. Sure ammonia could be gassed into DCM no problem there, but when it's refluxed the solubility of this ammonia is likely to greatly decrease. I don't mind the smell of ammonia like the next chemist but this sounds a bit obtuse. Even if this worked which I doubt in all sincerity that it would, you would have a basic solution with ergot alkaloids in it being essentially boiled for a long duration of time. Which you have said yourself is not a good idea...

So OP I guess while I'm still giving advice, I wouldn't use ammonia saturated DCM for your second soxhelet extraction. I would reccomend something polar that boils at a low temperature such as Acetone like in your tek Kash. Save the basification for later.

This is the last post I'll make about this matter. If you don't care about yield and wanna putz around with glass-ware that's your choice. I don't recommend it, nor do I see why anyone else should.

 

[Kash]

Its really pretty hard to measure losses because there is very little quantitative data on LSA amounts in these seeds. If you know of any please show me lol, I would love that. No, I cannot say that there are no losses becuase of this, and there is no guarentee that a sox extraction wont degrade the product, but it would still be interesting to see the results of say a 5hr extraction. I plan on doing more LSA work this summer with various extraction methods and chromatography, and hopefully produce some actual quantitative results.

But I really dont see why fact and evidence cant be associated with subjective experience. The fact of what happened was that I made an IPA extract which was distilled and processed into resin. It happened, its a fact. The statement that LSA remained relatively stable for a short duration of heat/air/light exposure is supported by the evidence that it produced a very powerful experience (magnitudes beyond 10 seeds) equally comparable to many cold solvent extractions of LSA I have performed. It is not evidence there was no degradation, it is evidence that there was not significant loss to notice any difference.

Going to agree with you InMotion though to the OP... if you dont want to risk loss of yield then just scrap the sox extraction and use a cold solvent extraction.

 

[zeekborg]

Thank you all for the feedback, first of all I am sorry for letting this sit stagnant for a couple of months, hell and high water, disease, lack of funding/time have all more or less put this little project on the backburner for me.

Secondly not going to lie did just do some shopping and wanted to try out some new glass that I bought. Did succesfully distill DCM and did an extraction on some fine buds with the soxhlet that i was very happy with. (going on a bit of a tangent).

Thirdly i would like to apologize for my lack of knowledge with respect to the chemistry, I thirst for more knowledge like a dry sponge and am looking forward to continuing my formal education in September.

I forgot to mention that I was aware of the heat, light, and air sensitivities of LSA hence to minimize them I intended to cover the glassware with tinfoil and if i can get my hands on some inert gas flush it out. I chose DCM as the solvent because i thought that a 40 degree BP should help to minimize loses due to heat (but i suppose I am wrong about this). Also I am familiar with how pH is measured but to be fair my knowledge is based upon 1st year courses and readings so there is still much to learn about acids and bases.

So to improve my extraction you are recommending an extraction that does not use heat and avoids basic conditions. then once I have some delicious juice use a method (such as garlic) to help break down all the nasties?

Lastly I would like to ask to those more experienced is the goal of having an end product with the potency of 1 drop = 1 moderate to strong dose even possible? Or will I have to settle with drinking a small vial of the stuff?