LSA extraction questions

[hCiLdOdUeDn]

I have thoughts of extracting, isolating, and purifying LSA from morning glory seeds. I know the morning glory seeds contain other alkaloid, oils, and resins. Is it possible to isolate LSA from seeds without chromatography?

Can LSA from morning glory seed extract be isolated & purified using a/b extraction techniques? I am asking this because I have never heard of LSA freebase or LSA salt. Is LSA similar to THC in that it cannot be in a salt or freebase from?

[Lilienthal]

Morning glory seeds contain d-lysergicacid-amide (Ergine) as the main alkaloid. Because it doesn't contain an acidic group and is not too hydrophilic it should be possible to do an A/B extraction. But that's not enough to get a pure compound.

[alphacentauri]

Check Erowid for some info about LSA:
www.erowid.org/chemicals/lsa/lsa.shtml

A few days ago I planted some morning glory seeds.
I will be much interested in the subject in the following seasons, presumably next autumn.
BTW, my seed bags reported:
IPOMAEA CAERULEA (Morning Glory) Ipomaea Coccinea L.
Is it the right one?
Ipomaea Coccinea is supposed to be the botanical name, while ipomaea caerulea the variety.
They are quite big, dark, sharp angled seeds.
Blue flowers.

[hCiLdOdUeDn]

Sounds like heavenly blue morning glory's.

Ipomea Tricolor = Ipomea Violacea = Ipomea caerulea

0.01% Lysergic acid amide by weight. E.G. 500grams of seeds will yield ~50mg Lysergic acid amide or ~100mg of total alkaloids that could be hydrolyzed to Lysergic acid.

If you planted HBWR seeds instead then 500grams of seeds would yield 200mg of lysergic acid amide or 1,500mg of total alkaloids that could by hydrolyzed to Lysergic acid.

HBWR seeds sounds like a better source for LSA.

[alphacentauri]

I know HBWR is a better source, but first you have to consider the availability of the plant. Morning Glory seeds are not so easy to find in these years, I had to go to an agricultural exposition to find them, but they are very easy to grow, if you have the space. And doing so, you can have an almost endless supply. The problem, eventually, is learning how to extract a pure product: from what SWIM read is not an easy extraction, but if you can have a large supply every year.....

[sean1234]

"Morning Glory seeds are not so easy to find in these years, I had to go to an agricultural exposition to find them"

what country do you live in? in the US you can find heavenly blues in any walmart . . . in fact they are easy to find. hbwr you can order online easily.

[alphacentauri]

[yellium]

[Madog]

SWIM would like to do an extraction on morning glory seeds or some HBWR seeds just for consumptin of the extract to avoid the other unnessisary things that are in there like cyanogenic glucosides taht give the unpleasent nasea and swim is also sure the liver must not like the things in there.

SWIM knows to soak in naptha first

SWIM also knows methanol and ethanol work good for the second soak to extract the beloved alkaloids but what other more volatile solvents can be used? such as diethyl ether, butane, or acetone? sience swim would need to evaporate the solvent without external heat the more volatile the better!

[GC_MS]

The distribution of indole alkaloids among certain species and varieties of Ipomoea, Rivea and Covolvulus (Convolvulaceae)

AD Marderosian, HW Youngken Jr. Lloydia 29(1) (1966) 35-42

Seeds of the morning glory, Ipomoea violacea L ("Badoh negro") and of Rivea corymbosa (L) Hallier filius ("Ololiuqui") are reported to be used in the uplands of southern Oaxaca in Mexico for divinatory and hallucinatory purposes. The credit for the recent rediscovery of the used of these seeds for ceremonial purposes may be attributed to several investigators (15,17,18,24,25) who have wirtten detailed accounts of this unique practice among the natives [...]

Material and Methods

The seeds were purchased from various commercial sources or obtained from different botanical gardens as indicated in table 1. Only viable seeds were used and all were subsequently grown in the Drug Plant Garden of the College of Pharmacy, University of Rhode Island for identification. At maturity, herbarium specimens were prepared for each and all material was subjected to botanical examination by comparison with specimens in the Harvard Herbarium to determine the correct species.
Two modification of the procedure of Hofmann et all (12) were used during the chemical examination of the powdered seeds; one in the qualitative studies and the other in the quantitative studies. For the qualitative studies 1 g of powdered plant material was mixed in a mortar with 0.5 g of sodium bicarbonate and 1 mL of water to obtain a thick pasty mass. The pH was 8 in all cases. One gram of anhydrous granular sodium sulfate was added to this paste and the whole was triturated until the mass became dry and of granular consistency. This was then transferred to a 50-mL Erlenmeyer flask along with 20 mL of dry ethyl acetate, the flask stoppered, and mixed on a shaker for one hour. The ethyl acetate extract was collected, and an additional 10 mL of ethyl acetate was used to re-extract the marc and the combined filtrates were poured into a separatory funnel.
The ethyl acetate extract was shaken with three 10 mL portions of 2% aqueous tartaric acid. The aqueous acid phase was drawn off, made basic with powdered sodium bicarbonate and re-extracted with three 10 mL portions of ethyl acetate. Fifteen uL of each extract was spotted on the TLC plates and 50 uL of each indole-positive extract was spotted on paper chromatograms.
The TLC system which proved successful in the resolution of these principles were aluminum [sic] oxide G with 5% methanol in chloroform (12), silica gel G with chloroform-methanol (17:3) (22), and silica gel G with chloroform-methanol-formamide (14:4:1) (1).
The most succesful of the paper chromatography systems was that reported by Agurell et al. (1) It involved the use of Whatman no 3 MM paper and a solvent system of benzene-pyridine (6:1) which was allowed to flow off the paper during development. The papers were pre-treated with benzoic acid dissolved in a methanol-formamide solution prior to spotting.
After separation was achieved by these chromatographic methods, the spots were examined and marked under short and long wave UV light. This was followed by spraying with modified Ehrlich's reagent (2% p-dimethylaminobenzaldehyde dissolved in a solution of 50 mL of conc HCl and 50 mL of EtOH) which caused the separated indols to appear as blue-violet spots.
For the quantitative determinations 1 g of each of the powdered seeds was first defatted with 250 mL of petroleum ether (bp 30-60) in a Soxhlet appartatus, then removed, air-dried, made alkaline and extracted with ethyl acetate as above. Aliquots of the final ethyl acetate extracts were taken for the colorimetric assay. The Michelon and Kelleher (16) modification fo the van Urk assay for ergot alkaloids was used for determining the total per cent of alkaloids in the seeds. The reported values (table 3) are ergometrine equivalents. [...]

1. S Agurell e.a. Analysis of clavine alkaloids of Pennisetum ergot. Lloydia 25 (1962) 67-77
12. A Hofmann. Die Wirkstoffe der mexikanischen Zauberdroge Ololiuqui. Planta Medica 9 (1961) 354-367
15. T MacDougall. Ipomoea tricolor, a hallucinogenic plant of the Zapotecs. Bol Centr Invst Anthropol Mex 6 (1960) 6
17. RE Schultes. A contribuation to our knowledge of Rivea corymbosa the narcatic ololiuqui of the Aztecs. Botanical Museum of Harvard University, Cambridge, Massachusetts, 45 pp (1941)
18. RE Schultes. Lecture 1, Jungle search for new drug plants in the Amazon: Lecture 2, Native narcotics of the new world: Lecture 3, botany attacks the hallucinogens. University of Texas, 3rd lecture series. Pharm Sci Part V pp 138-185.
24. RG Wasson. The hallucinogenic fungi of Mexico: an inquiry into the origens of the religious idea among primitive peoples. Harvard Univ Bot Mus Leafl 19 (1961) 137-162
25. RG Wasson. Notes on the present status of ololiuqui and the other hallucinogens of Mexico. Harvard Univ Bot Mus Leafl 20 (1963) 161-193.

The "missing part" of the article concerns discussions of the obtained results, particularly TLC results. I just typed over the potentially interesting part, viz. the extraction (both qualitative and quantitave).

[bbell]

Chemical Abstracts vol.63 column12003g(1965).
(species,variety,percent alkaloid on fresh wt. basis,given)
Ipomoea violacea,Pearly Gates,0.041, Wedding Bells,0.037,Flying Saucers,0.030,Heavenly Blue,0.029;I.nil,Royal Marine,0.001,Scarlet O'Hara,0.001,Darling,0.001;Rivea corymbosa,Ololiuqui 0.056%.No alkaloid was detected in I. nil var.Tall Mixed,Candy Pink, or Double Rose Marie

[sYnThOmAtIc]

Well whats wrong with taking a trip to kentucky or alabama witha sticka nd trash bag walking through peoples fields collecting grain?

Or why not take that time and energy of cultivation and just orrder some paspali cultures and just culture it in five gallon buckets. HEll five gallons of culture would provide 20grams of lsa.

Then if you want to grow plants go with sleepy grass or extract the fungus present in the grass and culture it. Or order it it can esily be bought as a live culture as well. I was reading a thing about fungi and there are like three or five species acromyces, claviceps and others that produce high percentages of lysergic aicd amide.

ANd then ther is always extracting it from cow shit, or urine take your pick.

http://oas.okstate.edu/ojas/benne02.htm

If i read that correctly at the end it concludes that 46 mg per day is excreted in urine.Hell after collecting and processing urine for a year you'd have plenty of lsa .
This last one is not viable and is only a joke. But the rest are much easier than growing and collecting seeds. You know, I have morning glory growing in my yard and it runs hte lenght of a 40ft fence 8ft high and it's totally covered you can't see the wood. For the hell of it one month I started helping them pollinate and collected the dead flowers for hte seeds. You know how amny seeds I got after a month of this B/S? 25grams. I dunno but after enough time has passed to have harvested 10kg of seeds the lsa will probably have degraded and would not longer be useful. Lysergic acid synthesis looks more friendly than growing plants.

[GC_MS]

I have a small city garden, which is partially consumed by some morning glory plants. Ipomoea violacea "Heavenly Blue" to be exactly. Here are some pics I made today.

The

Erowid Morning Glory Vault

(http://www.erowid.org/plants/morning_glory/morning_glory.shtml) holds some pics as well.





Most of the glory already gone...





General overview of this entheogenic weed.





Yet another overview, seen from the other side.





Just look at these psychedelic colours... Don't you think it's screaming 'I'm capturing solar energy to produce a bunch of LSA, which I can dump in my seeds, and all this just for you!'





Another flower loosing most of his powers...  





Delicious...  





Seeking contact with the Gods.





We are God.







Heeeeeeeeey!!! Which Bee is stealing my Honey here!?!!???  


Note: You can use the pics for whatever you want, except for making personal profits.

[bbell]

the full article can be found in Proc.Can.Soc.Forensic Sci.4,167-86(1965)by K.Genest et.al.
Another article worth mentioning Planta Med.9,354-67(1961)by A.Hofmann
Also Phytochemistry 2,99-101(1963)by W.A.Taber et.al.

[GC_MS]

Reference: K Genest. A Direct Densitometric method on Thin-Layer Plates for the Determination of Lysergic Acid Amide, Isolysergic Acid Amide and Clavine Alkaloids in Morning Glory Seeds.

Introduction

The discovery by Hofmann¹ that the ancient magic drugs "Ololiuqui" (Rivea corymbosa) and "Badoh Negro" (Ipomoea violacea) contain psychotomimetic substances prompted other workers to investigate ornamental varieties of morning glories which belong to the genus Ipomoea and Convolvulus. Taber et al.² found lysergic acid and clavine alkaloids in the seeds, embryo, leaf and stem in several horticultural varieties of morning glories. Similar results referring to the total alkaloidal content and the chromatographic identification of several ergoline alkaloids were published by Gröger³, Beyerman et al⁴ and Alexander⁵. Pharmacologically the most important of the alkaloids in morning glory seeds are lysergic acid amide (LAA) and its epimer isolysergic acid amide (isoLAA). Solms⁶ found that LAA is a psychotomimetic with strong sedative action. Information in the literature on the quantitative content of the individual alkaloids is limited to Hofmann's report on two large samples of Rivea corymbosa and Ipomoea violacea and on the analysis of Taber et al. of one sample each of Ololiuqui and Pearly Gates. The latter authors gave only relative percentage values of several alkaloidal components after elution from thin-layer chromatograms.
It is the purpose of this paper to present a method for the determination of lysergic acid amide, isolysergic acid amide and clavine alkaloids in morning glory seeds by direct densitometry on thin layer plates.

Materials and methods

Thin-layer chromatography (TLC) - Desaga equipment according to Stahl on 20x20 cm plates and 250 µ layers was used. The standard alkaloids were dissolved in ethanol or chloroform to contain 1 µg per µL. Morning glory extracts were prepared as described under "Total alkaloids". For qualitative TLC about 5 µg total alkaloids per spot were applied. The layer material used was MN-Silica Gel-HR' and Aluminium Oxide GF. After spotting the thin-layer plates were chromatographed until the solvent front reached 15 cm. The following systems were used:

(1) Layer: Aluminium Oxide GF; Solvent: chloroform:EtOH (96:4)³
(2) Layer: MN-Silica Gel-HR'; Solvent: acetone:piperidine (9:1)
(3) Layer: MN-Silica Gel-HR'; Solvent: acetone:ethylpiperidine (9:1)
(4) Layer: Aluminium Oxide GF; Solvent: acetone:ethylpiperidine (9:1)
(5) Layer: MN-Silica Gel-HR'; Solvent: acetone:EtOAc:DMF (5:5:1)³

After chromatography the plates were examined under 3660 Å and 2537 Å UV-light and sprayed with a solution of p-dimethylaminobenzaldehyde (DMBA).

Total alkaloids - Powdered morning glory seeds (1.0 g) were defatted by refluxing with petroleum ether (bp 30-60°) transferred into a Erlenmeyer flask (250 mL) and wetted with 5 mL of 10% aluminium hydroxide. Fifty mL of peroxide-free ether was added and the mixture was shaken mechanically for 30 min. The ether layer was then extracted with 5, 2.5 and 2 mL of 0.1 N sulfuric acid. The acid extracts were collected in a sparatory funnel. The extraction of the seed-ammonium hydroxide mixture was repeated with fresh portions of ether until judged to be complete by the absence of a grey-blue fluorescence in the acidic layer when irradiated with 3660 Å UV light. The combined acid extracts were made alkaline with ammonia and the solution was extracted with 20, 10 and three times 5 mL portions of chloroform. The chloroform extracts were collected in a 50 mL volumetric flask and filled up to the mark with chloroform. For the determination of total alkaloids two 5 mL aliquots were removed and evaporated to dryness in a stream of nitrogen. One mL of 0.1 N sulfuric acid and 2 mL of Van Urk reagent were added to the residue. After 30 min the absorbance at 550 mµ minus the baseline absorbance at 720 mµ were measured in a Beckman DK-2 spectrophotometer.
Van Urk reagent: 0.125 g DMBA was dissolved in 65% sulfuric acid (100 mL) to which 0.1 mL 5% ferric chloride was added.

[...]

Results

[...]

Alkaloidal content of morning glory seeds




[/red]

Horticultural variety	Botanical name	TA (%)	Origin	Remarks
Flying Saucers	Ipomoea violacea L.	0.057a	California
Heavenly Blue	Ipomoea violacea L.	0.023	Rhodesia
Major Tall	Ipomoea violacea L. and Ipomoea purpurea L. Roth	0.026	likely California	seed mixture
Pearly Gates	Ipomoea violacea L	0.032	California
Wedding Bells	Ipomoea violacea L.	0.030	California
Ololiuqui	Rivea corymbosa L	0.045	Cuba
Scarlet O'Hara	Ipomoea Nil L Roth	0.001	California
Darling	Ipomoea Nil L Roth	0.001	California
Royal Marine	Ipomoea Nil L Roth	0.001	England
Double Rose Marie	Ipomoea Nil L Roth	0.000	California	SFb
Tall Mixed	Ipomoea purpurea L Roth	0.000	Rhodesia	SF
Candy Pink	Ipomoea Nil L Roth	0.000	California
Crimson Rambler	Ipomoea purpurea L Roth	0.000	The Netherlands
Everblooming	Convolvulus tricolor L	0.000	likely Denmark
Moon Flower	Ipomoea alba L	0.000	Likely California
Fine Mix	Convolvulus tricolor L	0.000	Denmark	SF

Error: Table contains the text "[/red] " between [/td] and the next [/tr] markup tag in the table row "[tr][td]<font color="red">Horticultural variety</font color="red">[/td][td]<font color="red">Botanical name</font color="red">[/td][td]<font color="red">TA (%)</font color="red">[/td][td]<font color="red">Origin</font color="red">[/td][td]<font color="red">Remarks</font color="red">[/td][/red] [/tr]".

[a] Calculated for MW 262
Slight fluorescence in acidic extract.

[...]

[1] A Hofmann. Planta Med 9 (1961) 354
[2] WA Taber, LC Vining, RA Heacock. Phytochemistry 2 (1963) 65
[3] D Gröger. Flora (Jena) 153 (1963) 373
[4] HC Beyerman, A Van de Linde, GJ Henning. Chem Weekblad 59 (1963) 508
[5] TG Alexander, personal communications
[6] H Solms. J Clin Explt Psychopath Quart Rev Psychiat Neurol 17 (1956) 429

[catfish]

HC-
SWIM sez that tetrachloroethylene will defat as well as pet ether, and it dries faster. It will aso form the bottom layer, making final gravity filtration less of a chore.
Also, in order of preference based on SWIM's oneirogenic activities, extraction solvents are rated MeOH>EtOH>IPA>acetone>MEK. Methanol is toxic and not potable, ethanol is expensive, and IPA is dirt cheap. All three alcohols yielded colored xtals, while acetone gave only an oil, prolly due to rapid evaporation. MEK is toxic, expensive, undrinkable, and not worth it. Butane was not attempted, as the ergolines' polarity makes them an unlikely candidate for this solvent. Maybe as a defatting agent...
BTW, AFOAF sez Convolvulus=Ipomoea. However, that FOAF is often wrong...SWIM don't make this shit up, SWIM just relays the info.
-catfish

[bbell]

this synthesis is long and complicated, and out of the range of home organic chemistry.