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Author: Subject: Pyrolytic production of scopolamine from OTC precursor
Ritter
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[*] posted on 19-7-2008 at 09:43
Pyrolytic production of scopolamine from OTC precursor


Quote:
J Anal Toxicol. 2007 May;31(4):220-3.

Formation of scopolamine from N-butyl-scopolammonium bromide in cigarettes.

Frascht M, Schneider S, Schuman M, Wennig R.
National Health Laboratory, Toxicology Division, Luxembourg.

Scopolamine (hyoscine) is a naturally occurring alkaloid found in solonacea, the so-called "night shade" plants. Therapeutic applications of scopolamine are in ophthalmology to cause mydriasis and for the prevention of motion sickness, among others. It is known to induce hallucinogenic effects at a high dose. The N-butyl bromide derivative of scopolamine, available commercially as Buscopan, is commonly used as an antispasmotic. The possibility of forming scopolamine from N-butyl-scopolammonium bromide when burning cigarettes fortified with Buscopan was investigated based on a record of a prison inmate who claimed to experience hallucinations after smoking Buscopan. Liquid chromatography-tandem mass spectrometry in electrospray ionization mode was used to monitor the formation of scopolamine. Various series of eight cigarettes spiked with 10 mg of N-butyl-scopolammonium bromide with and without filters and in different smoking modes were investigated. The smoke of the burning cigarettes, the ashes, and the filter were analyzed for the presence of scopolamine. Scopolamine was detected in all cases.



I believe Buscopan is available OTC. I wouldn't advocate smoking it, but this looks like an interesting approach to synthesizing this alkaloid.

The temperature of a cigarette burning during drawing smoke is 700 deg. C.

One concern I would have relative to smoking this stuff is the possible production of HBr. The main concern I have is the very bad rap scopolamine has as the 'zombie drug.'

See http://en.wikipedia.org/wiki/Scopolamine.

There are a number of commercially available cellulose-based absorbents that would be a lot less expensive than cigarettes & that would not produce the tars & nicotine that would contaminate the alkaloid. Using a small air pump to draw the smoke from the burning absorbent-Buscopan into a series of cold traps might be one setup. The cold traps would sit in a mixture of Dry Ice & a solvent such as acetone or MEK.

This stuff is potent enough that extreme precautions would be required to handle any quantity safely: gloves, dust masks, etc. Scopolamine is an anticholinergic drug in the same class as the incapacitating agents such as BZ discussed in other threads. It is extremely potent. It can be absorbed through the skin. It causes anterograde amnesia (not being able to remember what you are doing).








[Edited on 19-7-2008 by Ritter]

[Edited on 19-7-2008 by Ritter]

Buscopan.gif - 8kB




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[*] posted on 19-7-2008 at 16:19


Scopolamine ( hyoscine ) is a major constituent of the alkaloid base of Datura species.
Datura is a common weed in Europe and parts of the USA and the seeds are widely available as they are grown as garden plants.
Cigarettes containing the dried leaves were available for the treatment of asthma at least into the later post war years.
The plant can be legally grown in Western Europe, the alkaloid could be extracted from the dried leaves.
Hyoscine intoxication is best described as unpleasant, probably why it never really caught on :cool:
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[*] posted on 19-7-2008 at 18:06


Quote:
Originally posted by ScienceSquirrel
Scopolamine ( hyoscine ) is a major constituent of the alkaloid base of Datura species.
Datura is a common weed in Europe and parts of the USA and the seeds are widely available as they are grown as garden plants.
Cigarettes containing the dried leaves were available for the treatment of asthma at least into the later post war years.
The plant can be legally grown in Western Europe, the alkaloid could be extracted from the dried leaves.
Hyoscine intoxication is best described as unpleasant, probably why it never really caught on :cool:


I guess when you are locked up in prison you take whatever you can get to help pass the time.;)

This report seems to indicate a more straightforward (if not highly problematical) means of experiencing scopolamine intoxication without first having to go through the labors of grinding, extracting, evaporating, etc., that would otherwise be involved with starting from natural product sources.

[Edited on 19-7-2008 by Ritter]




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[*] posted on 19-7-2008 at 18:38


Probably right.

Datura stramonium is a common weed around here.

http://en.wikipedia.org/wiki/Datura_stramonium

The plant is quite attractive, grown as a border annual, and the flowers
have a pleasant perfume in the evenings.
It is quite toxic but not more so than say hemlock which is commonly grown as a novelty plant in herb gardens!
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[*] posted on 19-7-2008 at 18:47


Although the complete synthesis of such an alkoid can represent a interesting chemical challenge, isolating scopolamine from another pharmalogical product in view of ingetsing it seems pretty cumbersome to me. I don't get it?

Preparing an infusion of datura is much more practical than isolating scopolamine from a pyrolysis via cold traps from a compound you must first aquire and possibly purify! In any case both procedures would be a piece of cake compared to a tropane alkoid intoxication.... I would really advise against such an ingestion, even (especially) in carciral environment.. Better stick to the nutmeg if you find yourself behind bars. :)




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[*] posted on 19-7-2008 at 18:50


Quote:

This report seems to indicate a more straightforward (if not highly problematical) means of experiencing scopolamine intoxication without first having to go through the labors of grinding, extracting, evaporating, etc., that would otherwise be involved with starting from natural product sources.

[Edited on 19-7-2008 by Ritter]


No point in any grinding, extracting, evaporating etc.
A nice fat joint filled with Datura stramonium leaves or a teaspoonful of the fresh seeds will introduce you to the experience of scopolamine poisoning without fuss! :cool:
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[*] posted on 19-7-2008 at 19:17


Quote:
Originally posted by ScienceSquirrel
Quote:

This report seems to indicate a more straightforward (if not highly problematical) means of experiencing scopolamine intoxication without first having to go through the labors of grinding, extracting, evaporating, etc., that would otherwise be involved with starting from natural product sources.

[Edited on 19-7-2008 by Ritter]


No point in any grinding, extracting, evaporating etc.
A nice fat joint filled with Datura stramonium leaves or a teaspoonful of the fresh seeds will introduce you to the experience of scopolamine poisoning without fuss! :cool:


I believe the point of this board is amateur experimentalism. Anyone can buy a packet of seeds & roll a joint, but what's the point in that? I'd rather learn from my curiosity & experience the isolation of (relatively) pure scopolamine from a legal, OTC starting material.




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[*] posted on 19-7-2008 at 20:39


Hyoscine ( scopolamine ) is legal over here as it is a common ingredient of sea sickness pills.
If I really wanted to purify some from OTC materials then I would start from there.
You are proposing carrying out a Hoffmann elimination on a derivative to produce the parent alkaloid. It will produce scopolamine but you are looking at preparative HPLC to separate it from the other stuff formed by side reactions at the same time.
Anyway if you mash around with this stuff you will experience the feelings of scopolamine poisoning unless you have a really good fume cupboard and a scrupulous technique.
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[*] posted on 20-7-2008 at 06:55


Quote:
Originally posted by ScienceSquirrel
You are proposing carrying out a Hoffmann elimination on a derivative to produce the parent alkaloid.


That reaction involves elimnation of tertiary amine hydroxides to form olefins. The hetero ring in scopolamine is fully saturated. While side reactions may likely occur under the pyrolysis conditions, the one that forms scopolamine is not a Hoffmann elimination. See http://research.cm.utexas.edu/nbauld/CHAPTER%2021.htm.


Quote:
It will produce scopolamine but you are looking at preparative HPLC to separate it from the other stuff formed by side reactions at the same time.
Anyway if you mash around with this stuff you will experience the feelings of scopolamine poisoning unless you have a really good fume cupboard and a scrupulous technique.


I did add plenty of caveats that this is potentially deadly chemistry & should only be attempted by technically competent operators using the proper equipment & safeguards.




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[*] posted on 20-7-2008 at 07:29


I don't see what the saturated nature of the amino-hetero ring has to do with the elimination.

On the other hand, the oxirane ring would seem to potentially be reactive if you whack the molecule hard.
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[*] posted on 20-7-2008 at 07:32


Quote:
Originally posted by not_important
I don't see what the saturated nature of the amino-hetero ring has to do with the elimination.


It just means it's not a Hoffmann elimination, which by definition creates an unsaturation.

Quote:
On the other hand, the oxirane ring would seem to potentially be reactive if you whack the molecule hard.


May be, but according to that report it survived a 700 deg C cigarette flame.




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[*] posted on 20-7-2008 at 08:10


Sorry I should not have called it a Hoffman elimination.

Anyway the parent alkaloid is found in motion sickness pills.

Quite why you would want to separate it out is beyond me but probably a lot easier than this pyrolysis stuff.
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[*] posted on 20-7-2008 at 08:23


Quote:
Originally posted by ScienceSquirrel
Anyway the parent alkaloid is found in motion sickness pills.

Quite why you would want to separate it out is beyond me but probably a lot easier than this pyrolysis stuff.


Scopolamine in the U.S. (patch, oral) is a prescription drug.




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[*] posted on 20-7-2008 at 08:32


YouTube 'zombie drug' video:

http://www.youtube.com/watch?v=xk0cV6JecV0&NR=1




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[*] posted on 20-7-2008 at 13:34


Datura stramonium is also a common weed here in New Zealand; also called "apple of Sodom", or "Jimson weed", with funnel-shaped flowers, prickly fruit, and narcotic properties.

However, it is often confused with with the five Brugmansia species, which are called "trumpet lily trees" or "angel trumpets", and widely grown in older gardens in frost-free areas here in which temperatures seldom fall below 7ºC, bearing velvety spade-shaped frost-tender leaves, trumpet-shaped sweet-smelling flowers (usually white, sometimes orange or yellow) to which bees are attracted, and elongated green fruit. I have some of the trees on my own property. Because of their soft foliage and spreading growth habit, chickens like roosting in them. The most common (white-flowered) species, which I have, is Brugmansia Arborea(Common Angels' Trumpets), which I think is the one I have,and Brugmansia Suaveolens. They are natives of South America, especially southern Brasil, Ecuador, Colombia, and Peru. All parts of the plants are toxic if ingested. I have seen drug addicts harvest their fruit, to boil down into an hallucinogenic drug.

[Edited on 21-7-08 by JohnWW]
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[*] posted on 10-1-2009 at 15:03
rjw


hi , what is OTC precursors ?

I have suppose a ''bond'' between atropine , ecgonine , tropane substances and incapaciting , psychotropic and other synthetic substances make in Edgewood Arsenal




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[*] posted on 10-1-2009 at 22:48


Ritter was apparently stumping to get Buscopan scheduled by DEA.

On the other hand I do not believe scopolamine is so scheduled. Until recently it was the active ingredient in Sominex.

Let sleeping threads lie.

These are delerium inducing compounds, jimson weed is better known as loco weed in western folklore often responsible for cattle and other livestock poisoning.

Scop is employed in surgery.

Recreational abuse of datura alkaloids is not unknown but most people regard the effects as highly unpleasant.

[Edited on 11-1-2009 by Sauron]




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[*] posted on 11-1-2009 at 03:17


Datura strammonium (as well as many other daturas) contain atropine as a major alkaloid, it is also psychoactive, but is known to cause more physical side effects, and to have lower ld50. Scopolamine is more hallucinogenic, and less toxic. It is also present d.strammonium, but as a minor alkaloid. It is major in D. inoxia, that was mostly used in all spiritual/zombification cases. D.inoxia is easily cultivated in any climatic zone, easily grown from seeds. But probably in cold areas it would not propogate by self-seeding as D.strammonium does..
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[*] posted on 11-1-2009 at 20:57


Scop is not a hallucinogen. Scop, atropine etc are delerium agents. Atropine is better known as belladonna, favorite poison of the Borgias. Do not sugarcoat these toxic alkaloids as some sort of fun trip. They aren't. All you are going to accomplish is to get some credulous and immature individuals sick or dead.



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[*] posted on 11-1-2009 at 21:39


@Sauron-right.. not sure what cause the hallucinigenic effects of Datura. The psychedelic state induced by these plants require doeses that are very close to those that cause permanent brain damage. One of the Manson clan, Tex Watson, was affraid of LSD so Charlie took care of him by having him ingest Datura teas. When the prison conducted a psi eval of Tex he tested as having an IQ of 65. There used to be OTC asthma treatment in the form of datura containing cigarettes... probably gone by now..

[Edited on 11-1-2009 by chemrox]




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[*] posted on 11-1-2009 at 22:03


They are cholinergic and muscarinergic. The neuropharmacology of the Datura alkaloids has nothing at all in common AFAIK with the hallucinogens. I think it is incorrect to even characterize their effects as psychedelic or hallucinogenic.

They are in same class as Ditran, QCB (BZ) etc.

Not at all benign and reportedly no fun which is why Ditran failed as a street drug.

I hear strychnine is a helluva high till your heart stops. Do you think anyone ought to experiment with nux vomica for fun?

I see little difference when it comes to Datura.




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[*] posted on 12-1-2009 at 01:11


To Chemrox and Sauron... Even though the effects of scopolamine, atropine and other anticholinergics have no resemblance to the effects of LSD and psychedelics in general, they certainly are hallucinogens - if not for else it is because hallocinations make part of delirium by definition (just ask any chronic alcohol addict). Actually they are even more of a hallucinogen than the psychedelic class of agents, simply because under the effects of psychedelics one generally does not loose reason and cognition abilities, while on deliriants it is simply impossible to have anything resembling rational thought - this makes it impossible to differentiate a hallucination from reality. Under the effects of psychedelics this can only occur under such heavy dosage to cause ego dissolution or under normal doses only in highly neurotic persons - otherwise all there is to be hallucinated is known to be just part of the trip and its origin tend to be recognized as internal rather than external as is the case with deliriants. I know this is all about psychological definitions, but I wanted to make it clear that deliriants certainly do cause visual, auditory and other hallucinations (and very heavily so!) besides other classical symptoms of delirium like psychotic thoughts, retrograde amnesia and loss of cognitive abilities.



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[*] posted on 12-1-2009 at 01:21


A recipe for a medieval witches' "flying ointment" was found some years ago, and it was made from hog lard into which was mixed ground-up aconite (and other plants of the genus aconitum, including monkshood and wolfsbane, the main active principle of which is aconitine), belladonna (atropine etc.), henbane (hyoscine, hyoscyamine, scopolamine), and I think hemlock (mostly coniine). Other versions also included less harmful ingredients, such as poplar leaves, basil, parsley, cannabis, cowbane, cinquefoil, hops, lavender, opium, and mandrake. Rubbed over the body, it was found not to really make one fly on a witches' whisk broom, but instead it created visual hallucinations of flying or out-of-body experiences, and someone who used it reported visions of "flying" to what looked like a "witches' sabbat" or "black mass". Is there anyone here game enough to try the stuff?

There are about 100 versions of this story on the internet, some of which are:
http://en.wikipedia.org/wiki/Flying_ointment
http://keepersoftheveil.com/forum/viewtopic.php?f=149&t=...
http://ms.linkfilter.net/?s=l&lid=141529
http://zenmind.org/curt-flink.html
http://www.answers.com/topic/flying-ointment
http://wapedia.mobi/en/Flying_ointment
http://www.paganwiki.org/index.php?title=Flying_ointment (gives exact proportions)
http://www.unexplainedstuff.com/Magic-and-Sorcery/Flying-Hig...
http://www.occultforums.com/bbs/showthread.php?t=10729
http://answers.yahoo.com/question/index?qid=20071023125416AA...
http://www.whitedragon.org.uk/articles/ointment.htm
http://www.hereticpress.com/Dogstar/Psychology/Hallucinogeni...
http://www.spiritgarden.co.uk/phpBB3/viewtopic.php?f=9&p...
http://www.shamanism.org/articles/article16page3.html
http://www.seasonsoftheearth.com/witchesbrew.html
http://temple-of-wisdom.net/archive26.html
http://en.allexperts.com/e/f/fl/flying_ointment.htm
http://www.paranormalhampshire.com/moon%20magic%20on%20bt/Lo...
http://www.realmagick.com/articles/33/2233.html
http://sajun.org/index.php/Flying_ointment
http://www.dailyom.com/library/000/000/000000135.html
http://wiki.healthhaven.com/Flying%20ointment
http://blog.myspace.com/index.cfm?fuseaction=blog.view&f...
(gives exact proportions, including cannabis)
http://cgi.ebay.it/FLYING-OINTMENT-SORCERY-SCENTS-ROLLERBALL...
http://www.websearch.com/rl/TB50109te10_sr-1/Flying-Ointment... (offers the stuff for sale)
http://www.angelfire.com/az3/synagogasatanae/four_mass.htm
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[*] posted on 12-1-2009 at 04:33


Well, there's an example of what is wrong with the Internet. About 100 versions of some medieval witchcraft bullshit, there;s a truly uplifting subject matter for the 21st century's information superhighway.



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[*] posted on 14-1-2009 at 02:12


One more flying oil, WITHOUT tropanes
http://www.alchemy-works.com/magick_oils_flying.html ;)
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