Sciencemadness Discussion Board - Pyrolytic production of scopolamine from OTC precursor

Pyrolytic production of scopolamine from OTC precursor

Ritter - 19-7-2008 at 09:43

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

ScienceSquirrel - 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:

Ritter - 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]

ScienceSquirrel - 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!

Klute - 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.

ScienceSquirrel - 19-7-2008 at 18:50

Quote:

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:

Ritter - 19-7-2008 at 19:17

Quote:

Originally posted by ScienceSquirrel

Quote:

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.

ScienceSquirrel - 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.

Ritter - 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.

not_important - 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.

Ritter - 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.

ScienceSquirrel - 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.

Ritter - 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.

Ritter - 20-7-2008 at 08:32

YouTube 'zombie drug' video:

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

JohnWW - 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]

rjw

ItalianXKem - 10-1-2009 at 15:03

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

Sauron - 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]

Ebao-lu - 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..

Sauron - 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.

chemrox - 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]

Sauron - 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.

Nicodem - 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.

JohnWW - 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

Sauron - 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.

Ebao-lu - 14-1-2009 at 02:12

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

Sauron - 14-1-2009 at 03:03

Yeah, well, I'm sick of all such New Age bullshit. This is supposed to be a scientific forum and not a magical one.

Leave that nonsense to Harry Potter.

ronstark - 24-7-2017 at 00:28

So, anyone figures this out yet? Freebase or salt compound?

[Edited on 24-7-2017 by ronstark]

tsathoggua1 - 24-7-2017 at 10:14

I could have a crack at this. Not that I'd intend on ingesting more than milligram quantities as an anti-nauseant. I have a prescription for buscopan 10mg tablets and I only use it occasionally. I've been having major stomach problems, and take buscopan, scopolamine itself in transdermal patch form (although I dropped that recently) cimetidine (my dr was mighty puzzled when whilst originally on ranitidine I asked him to switch me to cimetidine, and had no idea until I explained it to him about its effects, not shared with ranitidine, on hepatic CYP-P450 pathways, allowing my rx morphine, or the di/monopropionylmorphine mixture sometimes prepared from it, as well as rx oxycodone, to last longer and hit harder.

Taught him a new trick there, he was most surprised to have a patient teaching the doctor, rather than the other way around but it seemed to go down well, since he did do as asked and switch me over)

Dropped the patch scopolamine but still have a few to use if needs be for making comparison, since I got a script for ondansetron, which works absolute wonders for me, and stops me overloading my body with salts with the quantities of gaviscon I was having to consume daily (its been bad enough to land me in the ER, with projectle vomiting, sometimes blood-streaked, curled up in the foetal position and spewing bile and foam, after evacuating everything else. Until the first time I got given a shot of ondansetron which had me to rights in minutes, pulling out my copy of PIHKAL and TIHKAL from my backpack and heading out for a quick J and ending up falling asleep for a bit on a bench outside the hospital before some nurse, annoyingly woke me from my rest, the first in about 3 days of constant vomiting and billious retching every 5-10 minutes. Not fun) Also got put on cyclizine.

So now I have months and months and months and months worth of scopolamine butylbromide and if anyone can suggest a test to differentiate a quaternary ammonium salt from a tert. amine I'd be up for giving pyrolytic degradation a try to verify this.

Since this is a bromide salt, would adding a soluble silver salt work to test the pyrolysis product via abstraction of the bromide as silver bromide, and assay via its insolubility in acetone?

If anyone here has access to IR, UV or mass spec, NMR etc. I could perform the experiment and send a sample for assay to verify proportions of the quat to the tert. amine? since I literally have so much more of the scopolamine butylbromide than I could ever need and keep getting more every week.

[Edited on 24-7-2017 by tsathoggua1]

tsathoggua1 - 24-7-2017 at 10:42

Also, as far as new age bollocks goes, that oil may in fact have some oneirogenic properties.

Breaking down the more important ingredients...

Mugwort is the primary one I'd point out. It has a fairly long history in herbalism for stuffing pillows with the freshly dried herb, or its being smoked, as an oneirogen, I've tried it since it is very common round here and it did indeed seem to induce more vivid dreaming.

Hops contain humulones, isohumulones and lupulone and also produce as a degradation product of one of the constituents in fresh hops when aging 2-methyl-2-buten-3-ol, not far distant from tertiary pentanol, which is active and quite potent as a hypnotic/sedative with some characteristics in common with alcohol, I've tried the latter although not the olefinic derivative, and the active dosage to get quite 'pissed' would be a mere few ml.

Hops have a long traditional herbal usage as a sedative, as essential oil, as a stuffing of pillows. Interestingly the wiki article remarks on similarity of action to valerian. Has anyone here ever tried very high dose (with respect to dose suggested in OTC herbal valerian root extract capsules/tablets) valerian? it has some constituents similar to valproate, as well as a GABAa agonist active as an allosteric modulator of the loreclezole binding site and upon ingestion of say, an entire box of tablets (it is a sedative-hypnotic, although a mild one and this is not something that IMO is likely to overdose somebody dangerously, although still, test lower dosages first but do so in stages, separated by some time because one thing I noted was a MASSIVE tachyphylaxis to the oneirogenic effect such that it was very weak the second of two tests in a row, night after night, and third night pretty much ineffective, but the tachyphylaxis to the oneirogenic property is very short lived, but develops quicker than any other psychoactive I've ever known, even tachyphylaxis to fentanyl (had an RX for a brief time for my joint issues, hated it and day after went back to oxy and then to oxy and morphia)

Chamomile essential oils are also used as gentle relaxant-sedatives as is chamomile tea, well known for a long time for this use in herbal medicine. And saffron threads are known to be, when fresh, psychoactive. Trans-crocetin is reportedly a high-affinity NMDA antagonist, so this cocktail of oils and extracts together, whilst promoted as 'magick' and new age bollocksery heavily slathered over the top, does not, solely due to the WAY it is promoted as 'magic' render it by default, inactive bullshit. It may be presented as magic, but there is, whilst they may well not know it, science behind it that supports the potential for activity of such oil.

https://www.ncbi.nlm.nih.gov/pubmed/21112749

https://www.ncbi.nlm.nih.gov/pubmed/20537515

Think about it this way: the native amerindian users of ayahuasca traditionally for many thousands of years had no idea of the fact that DMT is the psychedelic component primarily, whilst orally activated by inhibition of monoamineoxidase-A enzyme, the Bwiti religion practitioners probably have no idea that ibogaine acts on 5HT2a receptors, NMDA receptors and many others besides, but they know it works. Whether they view the results as visitations from the gods, or spirits, doesn't make a difference to the fact that there is science behind their magick.

[Edited on 24-7-2017 by tsathoggua1]

ronstark - 24-7-2017 at 14:57

Too much hassle for only 10 mg. Just smoke it.

The smoke of the burning cigarettes, the ashes, and the filter were analyzed for the presence of scopolamine. Scopolamine was detected in all cases.

Quote:

Conclusions
This study has shown that smoking Buscopan tablets in cigarettes generates scopolamine,a well-known drug causing anticholinergic syndrome (hallucinations,mydriasis,and amnesia). Thus, the rare reports of persons claiming to smoke Buscopan should be taken seriously. Further studies are necessary to elucidate the chemical mechanism of scopolamine formation and to assess the quantity of scopolamine that needs to be absorbed by inhalation to experience CNS effects, such as hallucinations.

[Edited on 24-7-2017 by ronstark]

Attachment: Formation of scopolamine form N-ButylScopolammonium Bromide in Cigarettes.pdf (545kB)
This file has been downloaded 511 times