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#1 Aardvark

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Posted 17 March 2005 - 03:14 PM

:blink: --------------------------------------------------------------------------------

THUJONE


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

Thomas Prisinzano, Graduate Student
Department of Medicinal Chemistry
Medical College of Virginia Campus, Virginia Commonwealth University


Three Washington State doctors have recently issued a warning about medical products available over the Internet[1]. This is a result of a poisoning from the purchase of wormwood oil from a home computer. The victim was able to obtain, via the Internet, a recipe for making the banned liquor absinthe[2]. The victim was unaware that the consumption of absinthe may cause hallucinations, tremors, convulsions, and paralysis over the long term. The question that arises is what is responsible for the toxicity of the drink. The answer to the question is absinthe contains the compound (+)-thujone.
(+)-Thujone (1) is a widely occurring natural product found in the essential oils of two Artemisia species, Artemisia absinthium and Artemisia pontica. Wormwood oil, the oil obtained from Artemisia absinthium, is used as a counterirritant in Absorbine Jr. and Vicks Vaporub[3]. The French liquor absinthe was once prepared from wormwood leaves as well as several other herbs. Absinthe, however, was banned early in this century due to its toxicity. Thujone, one of the ingredients in the liquor, has been shown to cause of brain damage, and it is believed to be the compound responsible for the 1915 ban of the once highly popular drink in France.

Thujone is a monoterpene, or a class of natural products containing ten carbons, found in many different plants and flowers. Monoterpenes are derived from the coupling of two isoprenoid units, which are made from isopentylpyrophosphate, a precursor in the biosynthesis of cholesterol. These compounds are usually fragrance oils or low melting solids and are used commerically as aroma or flavoring agents. Thujone is structurally related to menthol (2), which is an old natural remedy for various ailments. Menthol contains a cyclohexane, or 6-membered, ring in its structure as well as an exocyclic isopropyl group. (+)-Thujone also contains a cyclohexane ring as well as the exocyclic isopropyl group. The essential difference is the presence of an additional 3-membered ring in (+)-thujone. This new ring results from an additional carbon-carbon bond between two of the members of the cyclohexane ring. The biosynthesis of these compounds is thought to derive from the same intermediate. The distinctive peppermint odor of menthol is found in Noxema medicated cream, Solarcaine, and Ben-Gay, as well as many other over the counter products [3].

The more notable use of (+)-thujone was in absinthe, a green liquor once very popular in the last quarter of the 19th century and the beginning of this century. The psychological effects of absinthe were believed to be different than other alcoholic beverages. The liquor was believed to enhance the activity of the brain, develop new ideas, expand imagination, and act as an aphrodisiac [4]. As a result, the drink became very popular, especially with artists and writers such as de Maupassant, Toulouse Lautrec, Degas, Gaugin, Manet, and Oscar Wilde [5]. Perhaps the most notable drinker was the troubled painter Vincent Van Gogh. During the last two years of his life, Van Gogh experienced fits of hallucinations and convulsions before his eventual suicide. His condition appears to have been worsened by his addiction to absinthe [6].

Absinthe drinkers were reported to have experienced a double action intoxication [5]. This intoxication combined the separate effects of alcohol and thujone. The alcohol produced a sedative effect in absinthe drinkers while the thujone is reported to have caused hallucinations (both visual and auditory) as well as excitation. The only proven effect of thujone, however, is its toxicity to the brain. The toxicity of thujone in the brain is believed to result from its structural similarity to tetrahydrocannibinol, or THC (3) , the active compound in marijuana. Cannabis has been used for centuries for medicinal purposes and has great therapeutic potential[8]. Thujone and THC have similar shapes, and it is believed that they interact with the same biological receptor to produce their similar psychological effects [9]. The similarities between the molecules include gem dimethyl groups and a similar carbon framework. It is also believed that the hydroxyl group of THC and the carbonyl of thujone may interact at the same site. Modeling studies show a good degree of overlap (4)(thujone in green; carbonyl oxygen in magenta).





Tremendous progress has been made recently in characterizing cannabinoid receptors, both centrally and peripherally [8]. It would be interesting to reevaluate (+)-thujone at these new receptor populations. (+)-Thujone is a potential cannabinoid ligand and might lead to the development of a new drug. :blink:





Date posted: 12/3/97





References
1. Weisbord, S. D.; Soule, J. B.; Kimmel, P.L. Brief Report: Poison Online - Acute Renal Failure Caused by Oil of Wormwood Purchased throught the Internet. N. Engl. J. Med. 1997, 337, 825.
2. Reese, K.M. Internet, World Wide Web put Absinthe within Reach. Chem. Eng. News 1997, 75, 80.
3. Sneden, A. T. in Introduction to Natural Products, Virginia Commonwealth University, Richmond, Va., 1995, p 81.
4. Vogt, D. D.; Montagne, M. Absinthe: Behind the Emerald Mask. Int. J. Addictions 1982, 17, 1015-1029.
5. Mann, J. in Murder, Magic, and Medicine, Oxford University Press, New York, NY, 1992, pp 105-109.
6. Arnold, W. N. Vincent Van Gogh and the Thujone Connection. JAMA 1988, 260, 3042-3044.
7. Arnold, W. N. Absinthe. Sci. Am. 1989, 260, 112-117.
8. Adams, I.B.; Martin, B.R. Cannabis: Pharmacology and Toxicology in Animals and Humans. Addiction 1996, 91, 1585-1614.
9. del Castillo, J.; Anderson, M.; Rubottom, G. M. Marijuana, Absinthe and the Central Nervous System. Nature 1975, 253, 365-366.
Is it true that cannibals don't eat clowns because they taste funny?

#2 Jack B

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Posted 17 March 2005 - 03:41 PM

Yeah, but one Thujone poisoning didn't stop me. 8 years later and I'm still drinking the stuff.

#3 Zman (Marc Bernhard)

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Posted 17 March 2005 - 06:54 PM

Old article, mostly disproven bunk.

If you don't like anise at all, you're not likely to care for any decent absinthe, as absinthe is an anise flavored drink. It's kind of like asking if there are any good beers that don't taste like hops or malt.----Hiram

Marc Bernhard, owner and Master Distiller of Pacific Distillery LLC
Maker of Pacifique Absinthe and Voyager Single Batch Distilled Gin and vodka.
Woodinville, WA, USA
www.pacificdistillery.com


#4 Gwydion Stone

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Posted 17 March 2005 - 08:20 PM

Yep. '97. And not so well researched, to boot:

It was suggested (Castillo et al., 1975) that thujone and tetrahydrocannabinol exert psychomimetic effects by interacting with a common receptor but this hypothesis is not supported by the work of Greenberg et al. (1978).

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#5 hartsmar

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Posted 18 March 2005 - 01:33 AM

and Ben-Gay


Uh oh!
Der blitze ist an der flachtmatuche

#6 Ari (Eric Litton)

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Posted 18 March 2005 - 12:45 PM

Speaking of thujone, does anyone have any detailed info about thujone building up in a rats system? What's the rate thujone is metabolized?
"Oscar Wilde once traveled to an all-cat dimension and appeared on the Late-Late Show with Catman O'Brien."

#7 Gwydion Stone

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Posted 18 March 2005 - 01:54 PM

Who gives a rat's ass? :harhar: You can't extrapolate rat data and apply it to humans.

The above-linked article covers it somewhat, but I don't think anyone has done a long-term effects study. They're usually pleased with being able to poison rats with ultra-high doses of wormwood oil right off the bat.

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#8 Absomphe

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Posted 18 March 2005 - 02:07 PM

Who gives a rat's ass?  :harhar:  You can't extrapolate rat data and apply it to humans.

<{POST_SNAPBACK}>


You're so right, Hiram.

I wish those researchers would start using humans as guinea pigs, instead of those tiny little rats that are unextrapolatable.

The world's way overpopulated, as it is.

Yes, I'm Krinkles the Clown on an absinthe a beer bender.

You got a problem with that?


#9 Ari (Eric Litton)

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Posted 18 March 2005 - 02:42 PM

That's what I figured. I was reading an article about unpublished tests where they gave the rats 10mg per rat kg a day (Otherwise known as the czech holy grail) for 38 days and the rats retained 5% of the thujone each day, allowing it to add up to a convulsive dose. They suggested that thujone built up in the system of chronic absinthe drinkers over time and eventually caused hallucinations (it's amazing the lengths some will go to to hold onto the thujone myth). Without knowing how quickly thujone is metabolized in rats (let alone humans) it seemed pretty pointless.
I have a test, lets give someone a shot of vodka every half and hour, if they die, it shows that alcohol can build up in your system over time, and years of casual drinking will kill someone. :)
"Oscar Wilde once traveled to an all-cat dimension and appeared on the Late-Late Show with Catman O'Brien."

#10 Gwydion Stone

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Posted 18 March 2005 - 03:18 PM

Where do I sign up?

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#11 G&C

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Posted 18 March 2005 - 04:34 PM

Is thujone paper something like wormwood barrels?

#12 Jack B

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Posted 18 March 2005 - 04:39 PM

Mr. Hyssop eats thujone for breakfast.

#13 Aardvark

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Posted 20 March 2005 - 08:17 PM

Sorry for dumping old data but it was new to me! Oh well. You can always use the thujone paper to wrap your fish. :blink:
Is it true that cannibals don't eat clowns because they taste funny?

#14 Gwydion Stone

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Posted 20 March 2005 - 08:57 PM

You may want to lurk and search over at Fe Verte. There's a lot of muck to wade through, but a lot of useful info if you're willing to work for it.

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#15 Gertz

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Posted 20 March 2005 - 11:26 PM

Is thujone paper something like wormwood barrels?

<{POST_SNAPBACK}>


Isn't it something like fly paper, to catch thujone?
+

#16 Gertz

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Posted 20 March 2005 - 11:28 PM

You may want to lurk and search over at Fe Verte.  There's a lot of muck to wade through, but a lot of useful info if you're willing to work for it.

<{POST_SNAPBACK}>


But less muck and more info than in the absinthe mosh pit.
+

#17 Absomphe

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Posted 21 March 2005 - 06:53 AM

  You can always use the thujone paper to wrap your fish. :blink:

<{POST_SNAPBACK}>


I'll find another use for it...

I like my fish fresh.

Yes, I'm Krinkles the Clown on an absinthe a beer bender.

You got a problem with that?


#18 G&C

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Posted 21 March 2005 - 07:22 AM

Get a new Kick from your home rolled.

Roll'em in Thujone Papers!

It'll make you tripbalz.

#19 Gatsby

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Posted 22 March 2005 - 09:40 AM

and Ben-Gay
Uh oh!

<{POST_SNAPBACK}>


Been Gay
I like to torture my plants by watering them with ice cubes.---Steven Wright

#20 Absomphe

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Posted 22 March 2005 - 02:17 PM

Now, now Gatsby...

Don't you be pickin' on my good friend the felon.

He SWEARS he's never been gay! :laf:

Yes, I'm Krinkles the Clown on an absinthe a beer bender.

You got a problem with that?


#21 thegreenimp

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Posted 22 March 2005 - 02:37 PM

Is thujone paper something like wormwood barrels?

<{POST_SNAPBACK}>



You use it to line the bottom of your wormwood casks.
At the close of the day drink an Herbsaint Frappé,...Legendre Herbsaint, always served when absinthe is called for.
The History of Legendre Herbsaint

#22 Gatsby

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Posted 22 March 2005 - 02:49 PM

Now, now Gatsby...

Don't you be pickin' on my good friend the felon.

He SWEARS he's never been gay! :laf:

<{POST_SNAPBACK}>


And I SWEAR everything he says is true.
I like to torture my plants by watering them with ice cubes.---Steven Wright

#23 hartsmar

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Posted 22 March 2005 - 11:09 PM

Oh... "Art" justifies anything these days... SHIT!
Der blitze ist an der flachtmatuche

#24 G&C

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Posted 23 March 2005 - 06:44 AM

Who's Art?

#25 Jack B

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Posted 23 March 2005 - 09:32 AM

Art


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