I have seen a little bit of talk about LSA in the bullshit thread, so I figured that we could place all information that we (or our friends) have obtained about this seemingly mysterious alkaloid in here and then from that information, progress to an isolation of the compound and further study of the pure product's affect on humans.

I will start

Here is some information I have for Hawaiian Baby Woodrose seeds, which are considered the most LSA rich plant seed.

Major Alkaloid Content in the seeds of A. nervosa(Burm. f.) Bojer:
alkaloid name---------% of Total alkaloid ---% dry seed weight
Ergine ---------------------------22.68--- 0.136
Isoergine ------------------------31.36--- 0.188
Ergometrine (aka ergonovine) ------8.20--- 0.049
Lysergic alpha-OH-ethylamide ------5.79--- 0.035
Isolysergic alpha-OH-ethylamide ----3.98---0.024

It seems that Ergometrine would be the compound that causes vasoconstriction when the primitive extracts of LSA containing seeds are consumed by most users as they only extract the alkaloids not the LSA specifically.

As far as I see, there appear to be no published procedures detailing how to eliminate LSA from the extracts, would this be possible at all? By my thinking, all changes that reactions would occur onto the LSA would affect all of the other compounds are they appear to be mostly similar.

Ahh finally the thread i wanted! I will copy pasta most of the info i have asap, but as stated before multiple chromatography seems the only answer to me :(

I once did a few h'experiments with HBWR, basically a quick methanol soak, and then, if I remember correctly, it was just basify-add-NP-extract-evap. Yes, evaporating random solvent based crap is not the best of ideas, but I was an idiot in those days, and I'm still alive now. Nothing special, so no pictures. :)

I once did a few h'experiments with HBWR, basically a quick methanol soak, and then, if I remember correctly, it was just basify-add-NP-extract-evap. Yes, evaporating random solvent based crap is not the best of ideas, but I was an idiot in those days, and I'm still alive now. Nothing special, so no pictures. :)

I was thinking something like that but with full clean solvents, sum reflux, sep funnel and nice hueg (liek an xoboxx!) chromatography column. Of course all of this 1-5kg batches!

This good really work the fuck out, seriously! Using also selective growth (if your that keen!) to reduced the number of "impurities" that they produce and adjusting it to tour personal please!

Crazy i say, not too hard, OTC (nearly), scalable is the win!

what is that chemical they put on the commercial seeds to cause nausea? I'm not talking about the mercury

what is that chemical they put on the commercial seeds to cause nausea? I'm not talking about the mercury

at a guess;

a) Possible fertiliser / pesticide residue on outer shell of seeds.
b) I believe I've seen somewhere evidence to show that HBWR, like many other seeds, contain cyanogenic gylcosides.

Ref for last claim ; http://www.erowid.org/plants/hbw/hbw_info1.shtml , towards the bottom.

SoH, you keep mentioning these large scale experiments. Do you mean turning the alkaloids into a certain popular ultra-potent chemical?

I don't have much information ATM, but hopefully a methanol wash followed by an A/B should isolate the alkaloids well enough. Would a solvent wash be worth it? What solvent? If anyone were to do this, getting a nice distillation setup to recycle the solvents would probably be a very good idea.

Edit: An interesting article on the history of LSA alkaloids and some chemistry and biochemistry. Im about to read it, but I just skimmed though it. http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1637017

This manuscript reviews the history and pharmacognosy of ergot, and describes the isolation/preparation, chemistry, pharmacodynamics, and pharmacotherapeutics of the major ergot alkaloids and their derivatives. A brief discussion of the hallucinogenic properties of lysergic acid diethylamide is also featured. An abbreviated form of the material found in this paper is presented in a 4-hour didactic format to third-professional year PharmD students as part of their study of vascular migraine headaches, Parkinson's disease, and naturally occurring hallucinogens/hallucinogen derivatives in the modular course offering Neurology/Psychiatry.

I don't have much information ATM, but hopefully a methanol wash followed by an A/B should isolate the alkaloids well enough. Would a solvent wash be worth it? What solvent? If anyone were to do this, getting a nice distillation setup to recycle the solvents would probably be a very good idea.



Alkaloid Extraction (short method)

Finely grind seeds (preferably woodrose) and add NaHCO3. Extract with ethyl acetate by soaking about one day. Filter and extract the ethyl acetate with tartaric acid solution. Basify the extract with NaHCO3 and extract it with ethyl acetate. Dry and evaporate in vacuum the ethyl acetate to get the alkaloids. Repeat this procedure on the seeds until no more residue is obtained. Alternatively, add 100 ml petroleum ether to 100 g finely ground seeds and let soak about two days. Filter, discard petroleum ether and let seeds dry. Add 100 ml methanol to the seeds and let soak about two days. Filter, repeat extraction with another 100 ml methanol and evaporate in vacuum the combined methanol extracts. The residual yellow oil contains the alkaloids.

For chromatographic purification of ergot alkaloids from seed extracts see Phytochem. 11,1479( 1972). For ergot extraction and separation see also Fr. Patent 2,089,081 (11 Feb 1972) and CA 79,105,457(1973). For a recent review of the ergot alkaloids see R. Manske (Ed.) The Alkaloids, vol. 15: 1-40(1975).
Extraction of Lysergic Acid Amides from Woodrose Seeds or Powdered Ergot

Reduce the seed material to a fine powder in a blender, and spread it out to dry. Grind it again if it is not fine enough after the first time due to dampness. Saturate the powdered seed material with lighter fluid, naphtha or ligroine. When completely saturated, it should have the consistency of soup. Pour it in a chromatography column and let it sit overnight. Remove the fatty oils from the material by dripping the lighter fluid or other solvent through the column slowly and keep testing the liquid that comes through for fats by evaporating a drop on clean glass until it leaves no greasy film. It will take several ounces of solvent for each ounce of seeds. Mix 9 volumes of chloroform with 1 volume of concentrated ammonium hydroxide and shake it in a separatory funnel. When it settles the chloroform layer will be on the bottom. Drain off the chloroform layer. Discard the top layer. Drip the chloroform wash through the column and save the extract. Test continuously by evaporating a drop on clean glass until it ceases to fluoresce under a black light. Evaporate the chloroform extracts and dissolve the residue in the minimum amount of a 3% tartaric acid solution. If all the residue doesn't dissolve, place it into suspension by shaking vigorously. Transfer the solution to a separatory funnel and wash the other vessel with acid in order to get all the alkaloid out. Pour the washings in the funnel also. Basify by adding sodium bicarbonate solution, and add an equal volume of chloroform. Shake this thoroughly, let it settle, remove the bottom layer and set it aside. Once again, add an equal portion of chloroform, shake, let it settle and remove the bottom layer. Combine the chloroform extracts (bottom layers) and evaporate to get the amides.



From PC.

You'd have to give your alkaloids an hour or two in some MeOH and NaOH, evap in vac, and extract with hot ethanol to get something really worth your trouble though.

-F☺rd

From PC.

You'd have to give your alkaloids an hour or two in some MeOH and NaOH, evap in vac, and extract with hot ethanol to get something really worth your trouble though.

-F☺rd

:( That doesn't sound too good. Too many chemicals and equipment. Why wouldn't an A/B work?

Edit: Shit...
Concerning the extraction and purification of LSA from HBWR, The alkaloids are
more polar than e.g. DMT or mescaline, and are probably water soluble to some
extent. Thus, while a crude extraction can be performed with methanol, the next
stage of purification may not be very good. Thus the general extraction method
for alkaloids is quite possibly not applicable here. That is why I want to have a
look at exactly what the original method was, although the journal seems obscure
to say the least. Another day in the Chem Abs section, I fear.

Could anyone with the Merck Index give me some solubility info on ergine? Please? :)

:( That doesn't sound too good. Too many chemicals and equipment. Why wouldn't an A/B work?

For which part, the extraction or the hydrolysis?

For LSA (the amide) an A/B would work fine, I suppose. (Though I think you will want to at least run a column.) For lysergic acid you'll need the extra chems.

-F☺rd

For which part, the extraction or the hydrolysis?

For LSA (the amide) an A/B would work fine, I suppose. (Though I think you will want to at least run a column.) For lysergic acid you'll need the extra chems.

-F☺rd

That doesn't sound so bad, but I don't have any glassware. Is there any way to make a ghetto column? I guess I couldn't do anything very interesting without the glassware anyway, though. :( Jesus, do you have a column?

That doesn't sound so bad, but I don't have any glassware. Is there any way to make a ghetto column? I guess I couldn't do anything very interesting without the glassware anyway, though. :( Jesus, do you have a column?

Everybody has glassware. :) Just check your fridge.

-F☺rd

Everybody has glassware. :) Just check your fridge.

-F☺rd

Yea, well, you know what I mean. I don't have a column and to be honest, I'm not exactly sure how to use one. Does it need to be glass? I'm sure I could make one out of copper if it doesn't need to be clear.

SoH, you keep mentioning these large scale experiments. Do you mean turning the alkaloids into a certain popular ultra-potent chemical?

Indeed, i mean hopefully :)

I mean common, with the exeption of buying ET in some back ass country or in Eastern Europe i can't really see a viable way, so start from scratch and work up and see what you can source!

From PC.

You'd have to give your alkaloids an hour or two in some MeOH and NaOH, evap in vac, and extract with hot ethanol to get something really worth your trouble though.

-F☺rd

Thanks for that! Looks good to me but but a column is defently called for at the end:) I would at least!

:( That doesn't sound too good. Too many chemicals and equipment. Why wouldn't an A/B work?

Edit: Shit...


Doesn't sounds to bad to me, something the average person with a little more funds and time and do, nothing fancy, the "worst" is running the column probably, but then again i am a freak and i actually like doing that :(:)


Could anyone with the Merck Index give me some solubility info on ergine? Please? :)

Sorry for it being late, there ya go:

Monograph Number: 5652
Title: Lysergamide
CAS Registry Number: 478-94-4
CAS Name: 9,10-Didehydro-6-methylergoline-8b-carboxamide
Additional Names: lysergic acid amide; ergine
Molecular Formula: C16H17N3O
Molecular Weight: 267.33.
Percent Composition: C 71.89%, H 6.41%, N 15.72%, O 5.98%
Literature References: Isoln from Rivea corymbosa (L.) and from Ipomoea tricolor Cav., Convolvulaceae: Hofmann, Tscherter, Experientia 16, 414 (1964). Prepn from lysergic acid hydrazide: Ainsworth, US 2756235 (1956 to Lilly); from lysergic acid and phosgene-dimethylformamide complex: Patelli, Bernardi, US 3141887 (1964 to Farmitalia). Microbiological production: Rutschmann, Kobel, US 3219545 (1965 to Sandoz).
Properties: Prisms from methanol, dec 242°. [a]205461 +15° (c = 0.5 in pyridine).
Optical Rotation: [a]205461 +15° (c = 0.5 in pyridine)

Derivative Type: Methanesulfonate
Molecular Formula: C16H17N3O.CH3SO3H
Molecular Weight: 363.44.
Percent Composition: C 56.18%, H 5.82%, N 11.56%, O 17.61%, S 8.82%
Properties: Prisms from methanol + acetone, dec 232°.

NOTE: This is a controlled substance (depressant): 21 CFR, 1308.13.

That doesn't sound so bad, but I don't have any glassware. Is there any way to make a ghetto column? I guess I couldn't do anything very interesting without the glassware anyway, though. :( Jesus, do you have a column?

I do :) Column are pretty easy to do, check out vogel lab manual is explains is well and covers all aspects of it IMHO.

Doesn't sounds to bad to me, something the average person with a little more funds and time and do, nothing fancy, the "worst" is running the column probably, but then again i am a freak and i actually like doing that :(:)

Exactly. :( I'm starting a fricken $7.25/hr job when I get home, sounds like I'm going to be needing to make some sacrifices. I wanted to get a Kawasaki when I turn 18, and if I'm spending money on chem I won't have money for a bike. Plus, there's gas, drugs, food, etc. Plus, I'm going to be moving off-island for college in a couple months, so it might be hard to ship my glassware to a dorm.

It looks like Merck failed. I don't see any solubility info there.:(

Exactly. :( I'm starting a fricken $7.25/hr job when I get home, sounds like I'm going to be needing to make some sacrifices. I wanted to get a Kawasaki when I turn 18, and if I'm spending money on chem I won't have money for a bike. Plus, there's gas, drugs, food, etc. Plus, I'm going to be moving off-island for college in a couple months, so it might be hard to ship my glassware to a dorm.

It looks like Merck failed. I don't see any solubility info there.:(

:( I just put away some money when i can :( and then i look at some item i really want or need and save up for it. Maybe you can't practice in uni but at least you can study. Took me two years before i could get my hands on any sort of glassware, meanwhile i just read read read and read, still do so know!

Its not because you can't perform the experiments that you have to stop! keep innovation!

Back to the lsa.....:)

moar info for you: http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1637017

:( I just put away some money when i can :( and then i look at some item i really want or need and save up for it. Maybe you can't practice in uni but at least you can study. Took me two years before i could get my hands on any sort of glassware, meanwhile i just read read read and read, still do so know!

Its not because you can't perform the experiments that you have to stop! keep innovation!

Back to the lsa.....:)

moar info for you: http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=1637017

I'm trying to decide whether or not I should buy some glassware and leave it in my parents house. I would only use it a couple months a year if I do. Do you think (not that anyone really knows for sure) glassware be more expensive in the future (enough to make it worth buying now) or should I just wait till I can use it to start collecting?

Wow, this is fucken weird, I was reading that article last night and was about to edit it in, but I forgot to press the save button. I thought you stole that link from me for a minute (:mad:) before I realized I never actually posted it.

Plus, I'm going to be moving off-island for college in a couple months

Where to?

:( Jesus, do you have a column?
Nope, it's about the only bit of glassware I don't have. I daresay a ghetto one could be made fairly easily.

Where to?

UH Manoa (http://www.uhm.hawaii.edu/). I think someone else here is going there in a few years, but I don't remember who.

Nope, it's about the only bit of glassware I don't have. I daresay a ghetto one could be made fairly easily.

Yea, but it wouldn't look nearly as nice. :(

UH Manoa (http://www.uhm.hawaii.edu/). I think someone else here is going there in a few years, but I don't remember who.

Ahh, right near some fresh Baby Woodrose seeds ;)

Ahh, right near some fresh Baby Woodrose seeds ;)

Oh, haha, now I see why you asked.
Well, I get home tomorrow, so hopefully I can start experimenting early next month.

UH Manoa (http://www.uhm.hawaii.edu/). I think someone else here is going there in a few years, but I don't remember who.



Dude... I know this sounds weird but do you mind if I visit when I do NSE next year?

Dude... I know this sounds weird but do you mind if I visit when I do NSE next year?

No, that would be cool. You're going to be at UH for 2 semesters? If you have msn you should add me (addy in profile).

No, that would be cool. You're going to be at UH for 2 semesters? If you have msn you should add me (addy in profile).

I'm not totally certain, but I know I want to spend at least 1 semester at UH.

errr how about going back on topic?

What solvent(s) are you thinking for the a/b and then for the column chromatography?
I do not have access to my info as of now, anyone know?

Plus what quantities of HBRW seeds are we talking about to get a workable amount of LSA? (1-5 g)

If all of this is too low yielding, ergocryptine (sp), was proposed at the hive, but i did not follow up on that.... :(

I'm very frustrated. :mad: What I thought was HBWR (because of the HBWR seed pod right under it, the heart shaped leaves, and the woody-vine appearance) actually isnt. The flowers are yellow and turn red as it ages, whereas HBWR are white or something. :mad: I know I found an HBWR seed pod, I just need to figure out where it came from. :mad:

I wish I checked back here a while ago, I've really been interested in LSA lately.

Its been hard for me to find much information on LSA. I can't find any trip reports, good dosage guides or extraction methods.
Since I messed around with a few HWBR ideas a while ago I got to sick to feel much. Much like nutmeg I felt these things needed enough research.

Since I'm taking chem this year (please don't flame for not learning it already, it's hard to learn enough online) I'm sure I will be able to understand more and I plan on messing around with basic entheogens that people don't know much about.

Anywho... I was searching and erowid has 2 guides for LSA from HBWR that won't get you sick, and one is liquid extraction. I figure I can perfect there guide and get lots of LSA. I might even want to try the LSA to LSD guide found in TIHKAL or in PIHKAL, they might also have an LSA preperation guide in that.

I'll post back later when I know more, for next year I'll already have my friends lab set up so we can mess around with lots of these things

IIRC, the LSA>LSD requires a lot of LSA. I don't remember the liquid extraction, but I think it was just a solvent extraction, which means you would get a very impure product. You should look up recrystallization on wikipedia. Thats a good article.

Anywho... I was searching and erowid has 2 guides for LSA from HBWR that won't get you sick, and one is liquid extraction. I figure I can perfect there guide and get lots of LSA. I might even want to try the LSA to LSD guide found in TIHKAL or in PIHKAL, they might also have an LSA preperation guide in that.

I'll post back later when I know more, for next year I'll already have my friends lab set up so we can mess around with lots of these things

Walking precedes running...

LSA to LSD is not just pissing around with solvent extractions and the like, it's doable, certainly, but you're going to need chemicals and equipment, not to mention a certain amount of laboratory pazzazz... ;)

Anywho... I was searching and erowid has 2 guides for LSA from HBWR that won't get you sick, and one is liquid extraction. I figure I can perfect there guide and get lots of LSA. I might even want to try the LSA to LSD guide found in TIHKAL or in PIHKAL, they might also have an LSA preperation guide in that.

I'll post back later when I know more, for next year I'll already have my friends lab set up so we can mess around with lots of these things

Walking precedes running...

LSA to LSD is not just pissing around with solvent extractions and the like, it's doable, certainly, but you're going to need chemicals and equipment, not to mention a certain amount of laboratory pazzazz... ;)


But yes, extracting the primary amide will make it less nausea-inducing, and further purification would make it suitable for elaboration...

That doesn't sound so bad, but I don't have any glassware. Is there any way to make a ghetto column? I guess I couldn't do anything very interesting without the glassware anyway, though. :( Jesus, do you have a column?

I made a ghetto chemistry thread a long time ago. You might be able to find it.