The tropane alkaloids are commonly found in plants of three families, the Solanaceae, Erythroxylaceae, and Convolvulaceae families. Having several legitimate medicinal uses, we are interested in their well-known toxic properties (the illegitimate uses). Plants in the Solanaceae (potato family) have the highest and most potent tropane alkaloids avaible for extraction.
Alkaloids derived from these plants, are very toxic, some of them can only be used for a minute dose for medical purposes.

Atropine is used as a sulfate salt. (Used as a mydriatic to dilate the pupils for examination) A. belladonna berry extracts found use as a CNS stimulant and is useful in treating poisoning cases, particularly anticholinesterase poisoning induced by organophosphorous insecticides and nerve gas and poisoning induced by the toxic principles of the mushroom Amanita muscaria. Nontheless, highly poisonous. Its poisoning set of symptoms is known as anticholinergic toxidrome, typical for other drugs with anticholinergic effects.
(blurred vision, choreoathetosis, coma, delirium, fever, flushing, hallucinations, ileus, memory loss, mydriasis, myoclonus, psychosis, seizures,etc.)

Hyoscyamine (also be extracted from plants of the Solanaceae family, notably Datura stramonium) is used to provide symptomatic relief to various gastrointestinal disorders and spasms. Its side effects and overdose include eye pain, blurred vision, restlessness, dizziness, arrythmia, flushing, faintness severe headache, nausea, vomiting, CNS symptoms: disorientation, hallucinations, euphoria, short-term memory loss and coma.

Scopolamine, (first isolated: Hyoscyamus muticus/Scopolia atropides) is a CNS depressant at high doses, and has been used in combination with morphine to induce "twilight sleep" before and during labor, and in smaller doses, to prevent motion sickness. The drug is highly toxic and has to be used in minute doses. Overdose causes delirium, delusions, paralysis, stupor and death. In medicine, it is usually used in the form scopolamine hydrobromide. It can be used as a depressant of the central nervous system, though it can cause excitement, restlessness, hallucinations, or delirium in the presence of pain, mydriasis (pupillary dilation), and paralysis of the eye muscles. When combined with morphine, it produces amnesia and a tranquilized state known as twilight sleep. Although originally used in obstetrics, it is now considered dangerous for that purpose. Sometimes side effects of scopolamine can be mistaken for symptoms of cancer because of the nausea and unequal size of pupils associated with brain tumors (yummy!). Scopolamine was and is used as a date rape drug and as an aid to robbery. It is preferred because it induces retrograde amnesia. Reports of techniques of administration include wafting the powder to the victim with a puff of air, drugged chewing gum, or even craftily dropping the powder into the collar of a shirt or the front of a woman's low-cut dress. So basically it easily administerable.

Plants containing tropane alkaloids:

Mandrake, Mandragora officinarum, All parts of the mandrake plant are poisonous. The plant grows natively in southern and central Europe and in lands around the Mediterranean Sea, as well as on Corsica.

Deadly nightshade, Atropa Belladonna is native to Europe, North Africa, and Western Asia, and has become naturalized in parts of North America. It is not nearly as common in the wild as many field guides would suggest. In areas where it has become naturalized it can often be found in shady, moist areas with a limestone-rich soil.

Datura stramonium, a plant common to Virginia, and other Datura species are widely distributed throughout the world. These plants have a long history of being used as both sedatives and as poisons. Extracts of Datura metel, sometimes called Hindu Datura, were used as knockout drops to lure virgiins into prostitution and then by the prostitutes to sedate their clients. Also known as jimsonweed.

Historic uses and relations:

During the Roman Empire deadly nightshade has been used to murder several politician. The Roman Legion also suffered severe losses due to Datura

Cleopatra is also reputed to have tested the effects of henbane and deadly nightshade on her slaves to investigate the possibility of using these extracts to commit suicide (she found the toxic effects too painful).

CIA, during the 1950s Project MKULTRA. But due to the hallucinogenic side effects of the drug, it wasn't suitable for a truth- serum and the project was subsequently abandoned. (Nazi doctor Josef Mengele experimented on scopolamine as an interrogation drug doing the WWII.)

In the 1960�s and 1970�s, their were a number of cases of poisoning due to jimsonweed when people ingested the plant to try to induce a high similar to cocaine.

Probable uses:

Drug poisoning. Tainting/poisoning batches of drugs (for several reasons). Rumor: atropine is sometimes added to other potentially addictive drugs; abuse of those drugs is then prevented by the "unpleasant" effects of atropine overdose.

Painfull and deadly poisoning. Tropane overdose can produce a very painfull death.

Incapacitating agent. Scolopamine and its derivates can be used very effectively as an incapacitating agent. A handy, but powerfull dispenser full of it (plus the necessary additives) will surely make the enemys time an unpleasant one (leaving him defenceless).

Infanticide. May this doesn't sound as much but...Datura species where used in Latin-America as a natural agent of infanticide. Combining this idea with the first one and you have a easy to get rid of your junkies and their brood...

Scopolamine is already used in various drugs and ways. As a rape drug, robbery, etc. Its properties to induce a hypnotic state, twilight-sleep, causes retrograde amnesia. Speaks for itself.

Related links and sources:

(Im for easy extraction but here are some patents for synthesis, maybe they can be usefull)

Tropane-derivatives, their preparation and use - US Patent 6395748

2 step process for preparing biologically active tropane derivatives and starting material - US Patent 5342949

Tropane analogs - US Patent 6982271

I believe that organic molecules containing unsaturated 7-membered carbon rings, particularly tropolone (C7H5O(OH), aromatic) and cycloheptatriene (C7H8, which reacts with carbonium cations like the triphenylmethyl cation, losing an hydride anion, to form the aromatic tropylium cation, C7H7+) and its derivatives, were first obtained from atropine extracted from deadly nightshade.

BTW Black nightshade, scientific name is solanum nigrum, so-called for bearing small black berries which are edible but tasteless (I eat them myself), and which is a very common introduced weed in New Zealand, is often confused with deadly nightshade.

"To isolate alkaloids from plants, the dried and powdered plant material is extracted with pet ether (or hexane, colemans etc.) first. This removes fats, oils, terpenes, waxes etc. This extract is discarded.

The material is now subjected to an alcohol extraction, eg with methanol or ethanol. The extract is evaporated to leave the crude alkaloids mixture.

This extract is partitioned between an diluted aq. tartaric acid solution and ethyl acetate. Other acids like citric acid can be used, and other solvents may substitute here. The ethyl acetate layer contains neutral and weakly basic alkaloids. Evaporate the solvent to isolate them.

The aq. layer is neutralised with NH3 or Na2CO3 and again extracted with ethyl acetate. The organic layer now contains basic alkaloids, while the aq. layer contains quarternary ammonium ions.

Many alkaloids can be isolated directly from the alkoholic extract by chromatographic methods. This is a separation which works well for tropane alkaloids (atropine, cocaine, scopolamine)."

Could this crude description really be appliable to extract scopolamine (hyoscine) from the plant datura/henbane? I have been looking for a tropane extraction paper specifically but couldn't find one. I only managed to find sources for patented synthesis or prescription for medical uses (spasm/motion-sickness)

Any oppinions or source regarding this tropane?

dont forget brugmansia (tree datura) as a very common source of tropane alkaloids.

The flowers have lower levels of alakaloids which increase at dawn or dusk, I am not sure about the fruit but i bet its fairly high (looks similar to banna passion fruit, also looks very tasty), the green leaves and stems are not taken for recreation only the flower with the anthas removed and most of the green part.

http://132.236.163.181/cgi-bin/dol/dol_terminal.pl?family=Solanaceae

I have mistaken nigrum for night shade(due to being told its nightshade) in my garden it is like a vine and has purple/white flowers with oval dark fruit very anoying and invasive anyway(New Zealand).

Do the green parts of nigrum contain toxic tropane like alkaloids aswell?

How about the leaves of tomatos, what levels of alkaloids would you expect to find in them.

the common Solanaceae's all have very similar flowers (all be it the size can vary wildly)

Hatal - Perhaps I misunderstood you. You are looking for ways to extract tropane? If so, perhaps these hits will help you.

Studies on tropane alkaloid extraction by volatile organic solvents: dichloromethane vs. chloroform (http://www3.interscience.wiley.com/cgi-bin/abstract/112369645/ABSTRACT?CRETRY=1&SRETRY=0)

Another link is this (http://www.springerlink.com/content/x025p42485885345/), although you need a subscription....which I happen to have, but of course my subscription doesn't go back to 1975..... damn.

Selective recovery of tropane alkaloids applying liquid membrane technique (http://hrcak.srce.hr/index.php?lang=en&show=clanak&id_clanak_jezik=5832)

If you can be bothered buying stuff Modern Alkaloids: Structure, Isolation, Synthesis and Biology (http://www.wiley.com/WileyCDA/WileyTitle/productCd-3527315217,descCd-tableOfContents.html)



Otherwise, salvaged from excerpts -

Sample preparation, tropane alkaloid extraction with chloroform�methanol�concentrated ammonia 15:5:1 (v/v/v), was followed by solid-phase extraction on Supelclean LC-18 cartridges. Optimized conditions and careful pH control resulted in high recovery and reproducibility.

Tropane alkaloids solid-liquid extraction methods were developed and comprised ambient pressure ones: extraction with hot solvent, extraction at room temperature, on ultrasonic bath as well as pressurised liquid extraction (PLE) techniques. The highest yields of l-hyoscyamine in methanol PLE method (3 x 5 min, 110 degrees C) and scopolamine extracted with 1% tartaric acid in methanol (15 min, 90 degrees C) were determined. A mixed-mode reversed-phase cation-exchange solid-phase extraction (SPE) procedure was optimised for simultaneous recoveries of L-hyoscyamine, scopolamine, scopolamine-N-oxide from plant extracts as well as quaternary alkaloid representative: scopolamine-N-methyl bromide. First three alkaloids were efficiently eluted (recoveries 80-100%) from an Oasis MCX cartridge with methanol-10% ammonia (3:1, v/v) solution, whereas for the quaternary salt tetrahydrofuran-methanol-25% ammonia (6:1:3, v/v) was used with recoveries 52-6%. HPTLC-densitometric assay on silica gel plates was elaborated at 205 nm without derivatization and included: single development (over a distance 9.5 cm) with acetone-methanol-water-25% ammonia (85:5:5:8, v/v) mobile phase for L-hyoscyamine and scopolamine separation, whereas for scopolamine-N-oxide and scopolamine-N-methyl bromide a second development (to a distance 5.5 cm) with acetonitrile-methanol-85% formic acid (120:5:5, v/v) was applied. Newly elaborated RP-HPLC-diode array detection method was performed on Waters XTerra RP-18 column with gradient of acetonitrile in 15 mM ammonia solution and alkaloids were baseline separated within 20 min. Both chromatographic methods were validated and their quantitative results were compared. Good correlation between HPLC and HPTLC quantitative results was measured (correlation coefficients of mean values were 0.92086 and 0.99995 for L-hyoscyamine and scopolamine, respectively). In the RP-HPLC method, which was from 1.5- up to 7-fold more sensitive than HPTLC, limits of detection (LOD) and limits of quantitation (LOQ, in bracket) were (in ng/microl) as follows: 0.25 (0.82) for L-hyoscyamine, 0.29 (0.97) for scopolamine, 0.13 (0.45) for scopolamine-N-oxide and 0.58 (1.91) for scopolamine-N-methyl bromide. By the use of the optimised chromatographic methods, 14 various samples from the leaves and fruits of Datura sp. were screened for L-hyoscyamine and scopolamine contents and the most promising samples were established.

I hope that some of these will help. It seems that ammonia/methanol/chloroform or DCM are good solvents for Tropane alkaloids.

Incidentally, I've worked out how to use the university subscription stuff to browse online journals, so if anyone needs something checked out, PM me and I'll have a look and see if I can get it.

I've uploaded a JACS article from the '20's on the synthesis of Tropanes and the analysis and purification of alkaloids, to my FTP folder, in the Science and Technology subsection.