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[*] posted on 15-9-2008 at 11:14
Sourcing natural products


I am looking to find the essential oil with the highest percentage of elemicin, or otherwise the oil in which elemicin is the easiest to isolate. I know about Myristica fragrans or nutmeg oil, but I am looking to explore other commercially available sources.

Is there a database that is good for searches like these?
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[*] posted on 15-9-2008 at 12:26


What is the Smell of the “Fruit Salad Plant”?: The Leaf Oil of Leionema ambiens (Rutaceae)
Joseph J. Brophy, Robert J. Goldsack and Paul I. Forster
Journal of Essential Oil Research JEOR > Mar/Apr 2006


http://ifile.it/ljutpmq


Abstract:
The leaf oil of Leionema ambiens was analyzed by GC and GC/MS. It was found to contain (E)-β-ocimene (0.1-11%, the majority being >10%), (Z)-β-ocimene (0.1-4%, the majority >2%), viridiflorene (6-7%), bicyclogermacrene (6-13%), globulol (6-7%), viridiflorol (4-6%) and (E,E)-farnesol (14-23%) as major components. Lesser amounts of sesquiterpenes and aliphatic esters, the majority being present in trace amounts, were also present and presumably give the oil its fruity aroma. Key Word Index: Leionema ambiens, Rutaceae, essential oil composition, (E)-β-ocimene, bicyclogermacrene, (E,E)-farnesol.





[Edited on 15-9-2008 by solo]




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[*] posted on 16-9-2008 at 03:18


Elemi oil (essential oil from Canarium commune) contains up to 10% elimicin, but the composition varies like in all essential oils. Besides you would need a seriously efficient distillation column and probably more than a single vacuum distillation in order to get elimicin of >80% purity. Just check how many other components this oil contains and their boiling points.



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[*] posted on 16-9-2008 at 03:44


Most likely a spinning band, computer controlled still, or else prep LC. Either way costly and slow.

The synthesis is not particularly arduous for compounds of this type. Elemicin is 3,4,5-trimethoxyallyl benzene. Myristicin is 3,4-methylenedioxy-5-methoxyallylbenzene. These are the principle psychoactive components of nutmeg, also rather toxic.

The most common starting point is eugenol (oil of cloves). However, others readily suggest themselves to anyone skilled in the synthetic arts. In short, there is nothing special about "natural" elemicin expect scarcity and the synthetic compound will be less costly, purer and just as effective.




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[*] posted on 16-9-2008 at 03:54


Quote:
Originally posted by Sauron
Elemicin is 3,4,5-trimethoxyallyl benzene. Myristicin is 3,4-methylenedioxy-5-methoxyallylbenzene. These are the principle psychoactive components of nutmeg, also rather toxic.

Actually it was never demonstrated beyond doubts that elimicin and/or myristicin are psychoactive. These claims were mostly of speculative nature rather than experimentally confirmed. It is much more likely the psychoactive components of nutmeg is some other compound(s) - there are plenty terpenes in there who could be candidates for the active components. Or maybe even some nonvolatile component given that 0.5ml of the essential oil has practically no effect on humans while the amount of nutmeg containing that much oil does. I would consider the active component of nutmeg to be still unknown and research should be done in this area (this is a question that should be answered properly given the widespread use of nutmeg as a spice).




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[*] posted on 16-9-2008 at 11:02


Well, it's hardly my area of expertise. I do remember being impressed (negatively) with the toxicity described for nutmeg in Merck. This was some time ago and I don't recall the details. But if I were someone inclined to experiment on oneself or others I'd approach with great caution.

The usual anecdotal accounts descrive the ffects of nutmeg as including a "feeling of impending doom." That does not sound like fun to me. Sounds like being a contemporary mortgage banker.

I am not disputing your remarks. I am reminded however of the similar controversies surrounding the substance thujone and the essential oil of wormwood (A.absinthium) the much demonized herbal for which absinthe is named. Supporters of the ban on absinthe maintained that absinthe drives people mad. Early toxicologists pointed to thujone as the culprit. Before and after the recent lifting of the ban in most of EU (there were places where it was never banned) and Switzerland, arguments raged about the controversy from almost every possible viewpoint. The prevailing view is that the high ethanol content along with adulterants in cheaper grades of absinthe were the toxic components. The thujone content is actually quite low and consistent with present regulatory maxima in EU. My former partner studied a lot of well preserved samples of century old absinthe by GC/MS.'

Still others, who really really wanted the legendary storied hallucinogenic properties to be true, opined that even if thujone was not so psychoactive (beyond being a mild GABA antagonist) there must be some minor and overlooked component in real absinthe that was hallucinogenic. This appears to be wishful thinking, but is damnably difficult to disprove (or prove for that matter.)

And at least at one time about 10-15 years ago there was a theory that thujone and THC shared a receptor site. This was just more wishful thinking.

I mention all this not to go OT nor to be argumentative but merely to draw parallels between the seperation science problems, and the other factors involved in evaluating problems like these. It is neither simple nor easy. I think it might be relatively easy to seperate nutmeg oil into several fractions, with identifiable and quantifiable components, and likely some overlap. These fractions might be evaluated individually for activity and thus some eliminated along with their components, thus reducing the problem set to a more manageable scope. The final assault will most likely be a highly demanding and costly prep chromatography one. This really sounds like a project for a multidisciplinary team.

[Edited on 17-9-2008 by Sauron]




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[*] posted on 16-9-2008 at 17:57


Quote:
Originally posted by Sauron

The usual anecdotal accounts descrive the ffects of nutmeg as including a "feeling of impending doom." That does not sound like fun to me. Sounds like being a contemporary mortgage banker.


[Edited on 17-9-2008 by Sauron]


Ha!

I have always wondered the result if 15 teenagers all took some substance one night together that was 'really wicked shit' whilst being drunk and stoned on pot (to simulate the normal state in which they relax and have fun) what they would describe the experience as. i speculate that psychosomatic tendencies compound if within a peer group and some of them may need hospitalisation for their 0.5g of NaCl posioning.
The point being that 'psychoactive' is so subjective that if coupled with know psychosomatic affects one can often not distinguish.
I know very little on how these parameters are measured in reality however, these are just musings.




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[*] posted on 17-9-2008 at 01:22


I know this is off topic, but the question of the original poster was already answered so I guess there is no harm done.
Quote:
Originally posted by Sauron
Early toxicologists pointed to thujone as the culprit. Before and after the recent lifting of the ban in most of EU (there were places where it was never banned) and Switzerland, arguments raged about the controversy from almost every possible viewpoint. The prevailing view is that the high ethanol content along with adulterants in cheaper grades of absinthe were the toxic components. The thujone content is actually quite low and consistent with present regulatory maxima in EU. My former partner studied a lot of well preserved samples of century old absinthe by GC/MS.'

I thought that the new absinthe was made legal because it now contains less thujone than the original ones made a century ago. What was the conclusion your former partner got from his analysis? Do the new brands (mostly made in Check republic) contain less or similar amounts of thujone?
Quote:
And at least at one time about 10-15 years ago there was a theory that thujone and THC shared a receptor site. This was just more wishful thinking.

Indeed, this was the study that finally measured the affinity of thujone toward CB receptors: Thujone Exhibits Low Affinity for Cannabinoid Receptors But Fails to Evoke Cannabimimetic Responses
Besides, it was my impression that the supposition behind the use of absinthe was that thujone and ethanol acted synergistically. Thujone itself is not particularly psychoactive unless at doses so high to be already physiologically toxic.




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[*] posted on 17-9-2008 at 04:28


19th century and early 20th century absinthe did not contain high levels of thujone. Despite the name, A.absinthium is not the primary herb used in making absinthe, it is quite secondary. The main herb is P.anisum, anise, or other species containing a lot of anethole, which is the main chemical component of absinthe after ethanol. These include green fennel and star anise.

An understanding of how absinthe is traditionally made demonstrates why larger amounts of thujone cannot be present. The herbs are milled and mixed in a steep with strong ethanol of grape origin - not fermented from corn or beets or grain etc but only from grapes. Typically, inexpensive grape alcohol is produced from the waste of wine production. The French call the resulting brandy marc, the Italians grappa. It takes a ton of pressed grapeskins to produce a liter of this, the stuff is pretty raw and is definitely an acquired taste. But absinthe cannot properly be produced from anything else, or even neutral spirits (vedka) if it is to be authentic.

The steep is diluted a bit then distilled. The essential oils pass over with the ethanol/water while the bitter principles remain behind. If the distillation is continued too long these bitter principles begin to come over and ruin the product.

The absinthe is at this point about 75-80 degree and is adjusted to 68-72 degree with water and then colorated. The coloration process is finicky and imparts the balancing flavors as well as the traditional peridot green color which is entirely due to chlorophyll and is perishable.

In order for thujone levels to be high, the amount of absinthium used would have to exceed the amount of anise/fennel/star anise (often a mix) and this simply is never done. The Scientific American article by Dr Wilfred Arnold, which postulated in the 1990s that antique absinthe contained 100 mg/Kg thujone, was entirely in error and was based on rather faulty conjecture only. Arnold was out to prove that absinthe was the cause of van Gogh's ear-cutting episode.

Antique absinthe made traditionally by the great firms of Pernod, Berger, etc. contained single digit ppms of thujone.

However the five great traditional makers accounted for only 20% of production while the rest was made by scores or hundreds of petty companies, who often used "industrial" (non-viniferous) alcohol, mixed their products up from essential oils (like modern pastis) and colored them green with hepatotoxic aniline green dye or Paris green rodenticide, and simulated the louche of real absinthe with tumeric. No wonder people went mad.

It is not correct that most contemporary absinthe is made if the Czech Republic. A few are and are invariably trash, such as Hills or Sebors. Much better absinthes are produced in Spain, and particularly in France and Switzerland. My former partner makes his Jade Absinthe labels in France on antique copper alembics. I named this product myself. I can honestly say, having no commercial interest in them whatsoever, that they are the finest in the world.

Rather ersatz absinthes are also made in Japan, Bulgaria, Russia, Brazil (where they use rum as bade, ugh!) and elsewhere.

A brand made in Ibiza is entirely from star anise, and is artificially dyed a radioactive green that strongly resembles the reanimator juice in the grade-B horror film of same name, I suspect it is sodium fluorscein.

The Swiss never stopped making absinthe despite the ban, it just went underground and was known as Le Bleu. It was bootlegged in the Neuchatel area at about 30 swiss francs a liter and bottled in second hand wine bottles with computer printed labels. I have several empties (having helped empty them).

Interestingly the Swiss never used star anise. regarding it as toxic. Their French associates in Pontarlier just across the Jura mountains did use it. I looked into this old controversy and discovered that at one time shipments of star anise were admixed with Japanese star anise, a different species and one reported to contain a toxic principle not found in Chinese star anise. This is most likely the origin of the Swiss prejudice.

Thujone's physiological effects are similar to camphor, both have been used in massive doses to induce clonic seizures as alternative to electroconvulsive therapy. It takes 500 mg-1 gram i.v.

Otherwise thujone is a mild transient GABA antagonist and therefore, is something of a risk for undiagnosed epileptics. Depressed GABA levels will result in higher electrical activity in the brain.

Some idiot chasing the Green Fairy drank 10 ml of oil of wormwood a few years ago and went into renal failure, but recovered. This was in the Pacific Northwest, but I am pretty sure it was NOT Polverone, who is anyway no idiot.

Likewise some idiot in the UK filled a yard glass with absinthe and downed it, he died of ethanol poisoning. Yard glasses are normally filled with ale, not hard liquor. A yard glass of creme de menthe would have probably killed him. Absinthe was overkill.




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[*] posted on 18-9-2008 at 00:54


Thanks. This essentially reinforces my opinion that absinthe has no effects other than ethanol intoxication. At least on me it has no effects distinguishable from other ethanol containing liquors, but I thought this could be due to the nowadays brands not containing much thujone or some other such reason. But I always found funny the obsession of some people with absinthe being something special while to me it looked no more than a stupid fashion thing.
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[*] posted on 18-9-2008 at 02:03


I'm sure you know the historical context.

Absinthe started as an obscure Swiss herbal tonic panacea abound 1790 and remained so till the rights were acquired by Henri Pernod. This coincided more or less with the phylloxera aphid blight of European vineyards, and so all Europe was deprived in great measure of wine and brandy for the better part of fifty years. Absinthe, largely ignored previously, became the drink of all classes because it was available.

The vintners eventually learned that grafting European vines onto American rootstock solved the problem. They searched for ways to reattract their consumers and part of their strategy was to demonize absinthe as a horrible mind altering poisonous beverage. They were joined by the temperance movement, which was organized by the (protestant) Christian churches. In Europe this was known as the Blue Cross movement. (In US it was the Women's Christian Temperance Union.) But in large measure it was really a commercial war between winemakers/wine merchants and absinthe makers.

In Switzerland the German-speaking cantons were home to eau-de-vie makers who looked down on the nouveau-riche Francophone absinthe makers like Pernod. The Swiss banned absinthe in 1910. France was the last in 1915. The French government wanted to sober the population up so they could be slaughtered in the trenches. But to give you some feeling for the real intent, the French tipped their hand by banning not just absinthe but ALL HERBAL LIQUORS. (Some years later they quietly amended the law to exempt some Catholic owned liqueurs such as Benedictine and Chartreuse.)

Pernod moved to Spain where they continued to makemabsinthe till 1957. A decade later Ricard bought the trademark and the powerful liquor conglomerate Pernod-Ricard was born.

A lot of money and effort was spent on the false demonization of absinthe, Emile Zola was paid to pamphleteer against the drink. I am sorry to say, but many early toxicologists were supported by the winemakers financially in order to "prove" that thujone drives men mad. Many of these scientific hired guns became eminent and are now icons of toxicology.

The US is now the only major country to persist in banning absinthe.

It's just a nice refreshing floral, perhaps somewhat effeminate drink. In the glass, it is no stronger than a highball. (One part absinthe, 3-5 parts water.)




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[*] posted on 18-9-2008 at 04:24


Hey Flip.

Don't know your location and doubt this can be sourced commercially but if you happen to live in Australia you might try your own steam distillation.

Melaleuca Squamophloia - Prickly leaf tea tree.
Principal components elmicin or (E) isoelmicin.

Steam distillation of one form of this plant has yeilded a stunning 81% elmicin.

If anyone ever got off their ass down here regarding native phytochemistry exploitation we could generate some high value exports.
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[*] posted on 24-9-2008 at 17:54


Quote:
I have always wondered the result if 15 teenagers all took some substance one night together that was 'really wicked shit' whilst being drunk and stoned on pot (to simulate the normal state in which they relax and have fun) what they would describe the experience as. i speculate that psychosomatic tendencies compound if within a peer group and some of them may need hospitalisation for their 0.5g of NaCl posioning.


This is funny! :P And true. Even in clinical trials it's not unusual to see a 20% improvement (NNT = 5), or even better results, in the control group.

Taking sugar pills would sure make getting high a lot cheaper :cool:




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