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Author: Subject: Extracting the alkaloid scopolamine from datura stramonium seeds?
Mike1.618
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[*] posted on 28-7-2006 at 02:24
Extracting the alkaloid scopolamine from datura stramonium seeds?


does anyone have a more effective technique for extracting the alkaloid scopolamine from datura seeds than the following, and can anyone confirm the validity of the following technique?

STEP #1 Grind 2 grams dantra seed in mortar and pestle.
STEP #2 Place seed pulp into test tube.
STEP #3 Use pipette to place 6mL methyl alcohol into test tube with seed pulp. (the entire contents of the test tube should be 9mL this includes alcohol and seed pulp.)
STEP #4 Shake very well.
Note 1: methanol soon turns a clear yellowish color.
Note 2: end of day one there was only a slight darkening of the alcohol.
Note 3: end of day two there was no change in the appearance of the methanol.
STEP #5 Filter methanol from seed pulp. (gravity filtration will work fine for this).
STEP #6 Pour 2 mL. methanol through seed pulp to wash any remaining alkaloids from the seeds.

NOTE: Upon evaporation of methanol you are left with a golden yellow crystalline powder. The total product of this extraction is 80 mg.
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Ramiel
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[*] posted on 28-7-2006 at 05:04


No triple posting, you're skating on thin ice Mike. Besides, organic exctractions are pretty basic organic chemistry. If you really aren't sure what would work or why, I think you should READ some good texts before you DO something that may HURT someone.



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Vitus_Verdegast
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[*] posted on 28-7-2006 at 09:00


Stay away from scopolamine. You'll probably end up in the hospital yourself if you attempt to pull this one off.



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DDTea
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[*] posted on 28-7-2006 at 09:25


Don't scare him; atropine and scopolamine aren't so bad. Just wear some decent gloves. But judging by this guy's post on totse [exactly the same] and his twisted intentions...you never know.



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[*] posted on 28-7-2006 at 09:31


Do take the advice given meanwhile you can read about it ...............solo.

---------------------------------------------------------------------------------------------

Alkaloid Production in Diploid and Autotetraploid Plants of Datura stramonium
Strahil Berkov1 and Stefan Philipov2
Pharmaceutical Biology 2002, Vol. 40, No. 8, pp. 617–621

Abstract
A comparative investigation of alkaloid production and accumulation in the roots and leaves of diploid (2n = 24), and C4 generation of induced autotetraploid (4n = 48) Datura stramonium L. plants was performed. Fifteen alkaloids have been determined in the roots and two in the leaves, at a level of 1% or more of the crude alkaloid fractions in both ploidy levels. Two 3-tigloyloxy-6-isovaleryloxy-7-
hydroxytropane isomers were detected for the first time in genus Datura. In the conditions of the prolonged photoperiod, hyoscyamine was the main alkaloid in the roots whereas scopolamine was the main alkaloid in the leaves of both ploid
forms. In comparison to diploids, the roots and leaves of tetraploids had a higher alkaloid content and scopolamine/ hyoscyamine ratio.

Keywords: Datura stramonium, induced polyploidy, tropane
alkaloids.


Excerp
....Alkaloid extraction:

Root and leaf samples (0.2–0.5 g) were ground up with sea
sand and macerated in 10ml 3% H2SO4 for 6 h at room temperature.
After filtering and washing of the plant residue with
5 ml of distilled water, the solutions were adjusted to pH 9–10
with 25% NH4OH and triple extracted with 10ml CHCl3. The
combined chloroform extracts were dried over anhydrous
Na2SO4, filtered and evaporated in vacuo to give the crude
alkaloid fractions. Thus obtained residues were resolved in
CH3OH for further analysis.

Attachment: Alkaloid Production in Diploid and Autotetraploid Plants of Datura stramonium .pdf (52kB)
This file has been downloaded 3972 times





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Vitus_Verdegast
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[*] posted on 28-7-2006 at 09:37


I know, but as you say it smells very much like totse...
Although I am all for Darwinism, I'm too weak-hearted to endure the vision of Mike1.618 becoming Mike]-∞[ by spilling the methanol containing the anticholinergic deliriants all over his little hands. ;)




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DDTea
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[*] posted on 28-7-2006 at 09:53


By the way, if you have your hands on some Datura seeds, I'd strongly recommend growing some! It's very uplifting and fun. I love my little datura plants, and I have one big one, maybe 8" high with very pretty/weirdish looking leaves. I can't wait for them to start flowering. Daturas are beautiful plants! [and you will get better alkaloid yields from fresh plants] :)



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[*] posted on 28-7-2006 at 10:17


I know, I know!:):) I'm a big fan myself.

For the moment I don't have place to grow these plants, but I can comfort myself with the 6 year old wild Atropa belladonna that is growing not far from my place. :D A stunningly beautiful plant!

Every year I go collecting seeds from above belladona and every Datura stramonium that comes on my way.

When I do have access to a garden again, I plan to get ahold of some Hyoscyamus, Mandragora and Scopolia species. Also a friend of mine has an Atropa acuminata from the Himalayas.




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knowledgevschaos
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[*] posted on 7-9-2023 at 18:09


Hello everyone: considering that this thread has been dead for over a decade, I'm not expecting too much from this, but here goes.
I have an angels trumpet plant, which contains atropine and other tropane alkaloids, and seeing that they are the main antidotes to most nerve agents, I thought it would be a fun project to try to extract them.
It looks like atropine is soluble in alcohol in all forms, and very soluble in water in salt form, but only somewhat soluble in freebase form.

Here is what I was thinking:
-Shred some dried flowers, and soak them in methylated spirits overnight
-evaporate the alcohol, leaving a residue which hopefully contains the alkaloids
-dissolve it in hydrochloric acid, converting all the alkaloids to their hydrochloride salts
-neutralize it with sodium hydroxide, precipitating the freebase alkaloids

I'm not too worried about poisoning, as the early symptoms (dry mouth, dilated pupils) are easy to notice, and effective antidotes exist. Of course I will still be taking precautions.

Have any of you done this, see any major problems with this extraction, or have any tips or dangers that I've overlooked?
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[*] posted on 13-9-2023 at 06:13


I think you should be somewhat careful with scopolamine, its the worst of this type of alkaloids and is active in very small amounts.
Its used as a robbery drug, saw that on tv long ago, quite scary stuff.

Whatever tropane containing plant you have you going to get (if sucessful) a mixture of alkaloids unless you are skilled enough in chromatography to separate them.
But i agree an extraction would be intresting if you have some kind of analysis tool to see what you have actually got in the end.
I have a belladonna bush in my backyard and it now has many black berries that is said to contain quite much atropin.
I never have tried any experiments though as its quite poisonus.
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[*] posted on 13-9-2023 at 20:16


The seeds contain a lot of alkaloids:
https://pubmed.ncbi.nlm.nih.gov/2792973/

Quote:
The alkaloid content was 2.71 mg atropine and 0.66 mg scopolamine/g of seed.


1 usual dose of atropine for human is 2 mg perorally or 1 mg parenterally. Curing organophosphate poisoning requires much higher doses but that is usually done on ICU.
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knowledgevschaos
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[*] posted on 17-9-2023 at 18:43


Thanks for the replies everyone, I can't believe I brought back a thread that's been dead for 16 years!
It looks like your article is on datura, not brugmansia, it looks like the alkaloid content in brugmansia are slightly less.

https://pubmed.ncbi.nlm.nih.gov/32911850/
"The toxic effect of the plant is mainly attributed to atropine and scopolamine, their averages in the flowers are 0.79 ± 0.03 and 0.72 ± 0.05 mg/g of dry plant, respectively."
It looks like I'll get only a few milligrams, even with all the flowers I've stored and dried. I guess in a way that's good, because any accidents will be less serious. I may also have to use the seeds or fruits.
It also looks like the properties of scopolamine are similar to that of atropine, so I'll probably get a mixture of the two alkaloids, as Mateo_swe said. If I can separate them I will, because I would rather not have an alkaloid so often used in taking advantage of people, but it probably won't be possible.
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[*] posted on 17-9-2023 at 20:30


https://sci-hub.ee/10.1002/jssc.201000779
Here they used flowers for the extraction. They got 1,1 g of crude mixture of alkaloids from 500 g of flowers. For the separation they used HSCCC https://en.wikipedia.org/wiki/Countercurrent_chromatography

Btw atropine poisoning although its typical symptoms is hard to diagnose because of its rareness. Antidotes used are physostigmine, neostigmine, pyridostigmine. The last two act only on peripheral system, the first one also passes through hematoencephalic barrier so is suitable also for curing central nervous system symptoms like coma.
https://www.revespcardiol.org/en-a-case-acute-iatrogenic-atr...

[Edited on 18-9-2023 by Fery]
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[*] posted on 27-9-2023 at 06:22


Atropine used to be used in the military as an antidote to some biological weapons and gases.
They had these autoinjectors that you just stab yourself in the leg and it autoinjects the atropine.
Quite painful my father told me. He had to try the autoinjectors but without the atropine in them.
Scopolamine is much more dangerous and potent.
It is said to be found in some south american brugmansias (dont know exactly what kind) in high amounts.
The common Hyoscyamus niger (henbane, black henbane, or stinking nightshade) contains Hyoscyamine and scopolamine.
They are easy to grow and the seeds contain much of the alkaloids.
Farm animals get poisoned when eating Hyoscyamus niger except pigs that are imune and are said to enjoy the effects (wikipedia info).
Old literature says witches used to make some ointment of the henbane plant and rub on the inside of their legs, then they went on a trip to meet the devil.
But modern science says the effects are highly unplesant and dangerous.
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[*] posted on 27-9-2023 at 15:30
regarding Brugsmansia


I have several plants. They are perennial in Upstate SC. I don't handle them. Every part of the plant is poisonous. Reactions to it vary. If you are a shaman in the upper amazon basin, this is your go to plant for visions. One story I read, possibly apocryphal, had a gentleman excising his genitalia after ingesting Brugsmansia.

I am going to propagate using a zip lock bag to contain the plant and rooting medium.

Glove up and decontaminate afterwards - unless you are dead set on changing pronouns.
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[*] posted on 3-10-2023 at 16:09


Hi, I make my own Littorine HCl, if you need any: 2-hydroxy-3-phenylpropanoic acid
let me know.

pm or mlphoneuse atgmailcom





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[*] posted on 13-11-2023 at 21:53


Yeah, a lesson to all the curious out there, let me just start, and finish, by saying, noooo. Not this one. Trust me , there is NO good sensations to be had by meddling with these compounds, none at all...
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[*] posted on 10-4-2024 at 02:54


I think you should see this VICE documentary about scopolamine before you make up your mind about trying to make or isolate some.

https://www.youtube.com/watch?v=ToQ8PWYnu04
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[*] posted on 2-7-2024 at 16:38


Nightshade is a common weed here in Oregon. I do not recommend experimenting with Nightshade Alkaloids.

Hallucinogenic they are, but very unpleasantly so.

Imagine a fevered delirium, wherein your consciousness is divorced from ordinary reality. Feverish nightmares might well describe the effect. Bad stuff!

These Alkaloids have some medical uses, but no recreational uses.

I have multiple plants springing up, on my property right now. I recently offered the seeds(free!) to a seed vendor.
She expressed some strong reservations about whether she might sell them. An herbalist (or a naturopath) might find uses for the plants, or maybe not.
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[*] posted on 3-7-2024 at 18:05


I’d agree with zed, for anyone legitimately interested in extracting scopolamine or related tropane alkaloids.

The Ipomoea family may be a better crop to extract interesting chemicals from :P
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[*] posted on 4-7-2024 at 09:53


There is a lot of wisdom in this thread. Beyond the physical and psychological hazards of being delirious, I have heard reports of long-term negative effects from experiments with anticholinergics, and I even notice concerns that the anticholinergic component of ordinary things like diphenhydramine that a lot of us use to occasionally get sleep might contribute to mental decline with aging. The attraction of understanding ourselves better by busting open our own minds occasionally is understandable, but we have to do our best to limit the damage from that, obviously.
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[*] posted on 5-7-2024 at 05:23


Jenks, anticholinergic substances cause memory problems, it is well known fact. Substances which inhibit acetylcholinesterase thus increase the level of acetylcholine (donepezil, rivastigmine, galantamine) are used to treat dementia. For sleeping disorders treatment - modern hypnotics act on omega 1 site of GABA receptors (zolpidem, zalepon, zopiclone) without anticholinergic side effects. Elderly people are much more vulnerable to anticholinergic side effect than young, this is due to aging of neuronal cells, reducing their number and connections (synapses). Young people still have quite enough redundancy of neuronal cells, synapses and pathways. Brains of elderly people already operate without such enough redundancy so even slight inhibition of acetylcholine cause significant alteration of memory / cause severe delirium and so on.
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[*] posted on 7-7-2024 at 20:38


Some botanical info, just be careful if trying to extract these toxic compounds.

Scopolamine is found in the highest concentrations in a special variety of brugmansia (tree datura, devils trumpet) growing naturally in south american countries and sometimes as an ornamental plant as they have very nice huge trumpet like flowers.
It can also be found in Scopolia carniolica in high concentrations.
It´s also found in more common plants as Henbane (Hyoscyamus niger) and in higher amounts in Hyoscyamus muticus, the Egyptian henbane.
It´s also present in some Daturas as Datura stramonium and Atropa belladonna.
Atropa belladonna is one of the most toxic plants known. All parts of the plant contain tropane alkaloids, roots have up to 1.3%, leaves 1.2%, stalks 0.65%, flowers 0.6%, ripe berries 0.7%, and seeds 0.4% tropane alkaloids. All daturas contain atropine, hyoscyamine, and scopolamine in various levels.
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