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ThujoneErebusHippie33 1 09-04-03  02:04 pm

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Hippie3 (Admin)
Posted on Monday, August 18, 2003 - 02:13 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

goblettitle


What is Absinthe?
Absinthe is bright green liquor flavored using an herbal extract. The drink was popular in the 19th century especially in France within the bohemian crowd. The drink is green in color due to the chlorophyll. Due to the drink's very potent nature, it was traditionally diluted with cold water. The water is added through a perforated spoon containing sugar. When the water was added to the drink, it goes from the emerald green color to a cloudy white color. This occurs because the water causes the essential oils from the herbal extract to precipitate out of the alcohol and form a colloidal suspension.
Chronic use of absinthe leads to absinthism(1). The symptoms for this addiction include epileptic attacks, delirium, and hallucinations. Due to this and other social considerations, absinthe was banned in many countries during the early part of the 20th century.

A typical recipe for the herbal flavoring extract, attributed to Henri-Louis Pernod, calls for a ground up mixture of aniseed, fennel, hyssop, lemon-balm, angelica, star anise, dittany, juniper, nutmeg, veronica and wormwood. A steam distillation of this mixture is done. More wormwood is added to the distillate and then diluted with ethanol to 75% alcohol by volume(2).

The drink, which is supposed to be green in color due to the extracted chlorophyll, in the past was often made more green artificially by the addition of copper sulfate, cupric acetate, turmeric, and aniline green. Antimony trichloride was also added to aid in the color change when water was added(2).

These additives increased the toxicity of the drink but the more important problem is the extract from wormwood (Artemisia absinthium)(1). Wormwood contains the compound absinthin(3), which is responsible for the bitter flavor of the liquor, but the main toxicant in the essential oil is the compound thujone(3). It is known to be psychoactive and is the main active ingredient in absinthe other than the alcohol.

plant


Thujone

Thujone belongs to the family of monoterpene ketones(4). There are two principle enantiomers found in wormwood, (-)-3-iso-thujone (a-thujone) and (+)-3-iso-thujone (b-thujone). They make up 90% of the wormwood oil's weight(1), but a-thujone has a much higher toxicity than b-thujone. The ratio in nature of a to b-thujone is 1:2(4). The IUPAC name of thujone is 4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one.


mole diamole diagram


Properties

Thujone is a colorless liquid with a menthol-like smell. It is insoluble in water but soluble in ethanol, di-ethyl ether and chloroform. Thujone is found in other plants including cedar leaf, sage, tansy, thyme, rosemary and thuja (its namesake)(1). Trace amounts can be found as a flavoring agent in alcoholic beverages such as vermouth (wermuth, German for wormwood), chartreuse, and benedictine(1). Traces can also be found in Vick's Vaporub™, perfumes, and in pest repellents for rodents and mites(4).

Pharmacology

Thujone has been used in herbal medicine and was said to cure digestive problems, worms, menstrual problems, corns, warts, acne, fever, cough, rheumatism, scurvy and dropsy. It is reported to have antinociceptive, insecticidal, and anthelmintic activity(4). Rice and Wilson found that a-thujone had comparative antinociceptive effects to codeine when injected subcutaneously in rats using the hot plate test (ED50= 6.5 mg/kg)(5).
RouteSpeciesLD50[mg/kg]
OralRat500
IntravenousRabbit0.03
SubcutaneousMouse
Mouse
Rabbit
2.16
87.5
0.36
DermalRabbit5000

Table 1: Acute Toxicity Data for a-thujone(4)


Other cultures have discovered thujone's intoxicating effects. In West Bengal Artemisia nilagirica (a thujone containing plant) is smoked for its psychoactive effect and the Zuni smoke Artemisia caruhii as an analgesic(1).

Mode of Action

For a while it was hypothesized that thujone and tetrahydrocannabinol had the same site of action. This was believed to be true because of the similarities in their structures and effects(6). But in 1997, it was shown that neither thujone nor wormwood binds to the cannabinoid receptor(7). Until recently it wasn't known what the mode of action for a-thujone was but a recent study done by Hold et al. at Berkeley have found the toxin's mode of action(8).

They discovered that a-thujone is a modulator of the g-aminobutyric acid (GABA) type A receptor.(8) They compared a-thujone toxic effects to that of picrotoxinin, a GABAA receptor antagonist. It was found that they both had similar toxic effect and the toxicity in both was suppressed by diazepam, phenobarbital and ethanol. They also found that drosophila that had a single point mutation in the GABA receptor that made them resistant to dieldrin were also resistant to a -thujone. a-Thujone was found to be a competitive inhibitor of [3H]EBOB binding, i.e., of the noncompetitive blocker site of the GABA-gated chloride channel.(8) a-Thujone was also found to be a reversible modulator of the GABAA receptor in the dorsal root ganglia neurons.
chart

Figure 1. a-thujone and 7-hydroxy-a-thujone inhibit [3H]EBOB binding to mouse brain membranes (A) IC50 determination for a-thujone and 7-hydroxy-a-thujone (B) [3H]EBOB and with a-thujone(8)


These researchers also found that a-thujone is rapidly metabolized in mice liver with NADPH (cytochrome p450). The metabolites from its breakdown are 7-hydroxy-athujone (major) and other hydroxythujones (minor). a-Thujone is found to 56 times more potent in a [3H]EBOB binding assay than 7-hydroxy-a-thujone. 7-hydroxy-a-thujone was also found to be less toxic to mice and houseflies.

chart2
Figure 2. Structures of a-thujone (1S, 4R, 5R-thujone) and its metabolites in the mouse liver microsomal P450 system (8)


Famous Drinkers of Absinthe

While the use of wormwood can be dated as far back as 1550 B.C.(2), it became the rage in France starting about 1850. Its' use took hold in the intellectual and artistic comuntities and many famous people, Hemingway, Baudelaire, Picasso, and Degas drank absinthe(1It was thought then that it simulated creativity and acted as an aphrodisiac. Perhaps the most famous drinker of absinthe was Vincent Van Gogh for it appears that his depression, psychotic behavior and suicide were related to his chronic use of the drink. Van Gogh suffered from acute intermittent porphyria. The symptoms of this genetic disorder include attacks of abdominal pain, anxiety, hysteria, delirium, phobias, psychosis, organic disorders, agitation, depression, and altered consciousness fromtiredness to coma.(1) It has been theorized that the drinking of absinthe may have triggered these attacks.
van gogh


Regulation

Absinthe was banned in the United States in 1912 as part of the Food Inspection Decision 147. Thujone was banned as a food additive by the Federal Food, Drug and Cosmetics Act of 1972. In 1975, the Federal Food and Drug Administration designated thujone as an unsafe herb. But many thujone containing food additives, such as sage and rosemary, have been given Generally Recognized as Safe (GRAS) status by the FDA(4).

In Europe, a limit on the amount of thujone contained in food has been set by the European Community Codex Committee on Food Additives. The acceptable level is 0.5 ppm (mg/kg) in foods and beverages, 10 ppm in alcoholic drinks above 25% alcohol, 5 ppm in alcoholic drinks less than 25% alcohol, and 35 ppm in bitters(4).

Although absinthe has been banned in the United States, it is still legal in Spain and some other contries in Europe. The drink also has a "cult" status on the web where absinthe can be ordered and recipes for homemade absinthe can be found.

Other Considerations and Concerns

Thujone has also been found to be volatile enough that it is emitted from plants into the atmosphere. a and b thujone emissions have been measured near California sagebrush(4). New concerns as to consumer and worker exposure have lead to new research into its neurotoxicity.

Other Artists and Absinthe

(list from http://itsa.ucsf.edu/~mbagg/roughabsinthefaq.html)
Famous absinthe users include:

Edouard Manet
Charles Baudelaire
Paul Verlaine
Arthur Rimbaud
Oscar Wilde
Ernest Dowson
Edgar Degas
Henri de Toulouse-Lautrec
Vincent Van Gogh
Adolphe Monticelli
Paul Gauguin
Alfred Jarry
Pablo Picasso
Ernest Hemingway

Visual artworks inspired by absinthe include:

Edouard Manet's 1859 The Absinthe Drinker
Jean-Francois Raffaelli's 1861 Absinthe Drinkers
Honore Daumier's 1863 Absinthe Lithographs
Edgar Degas' 1876 L'Absinthe
Henri de Toulouse-Lautrec 1887 Portrait of Van Gogh
Vincent Van Gogh's 1887 Still Life with Absinthe
Henri de Toulouse-Lautrec 1887 Portrait of Van Gogh (pastel)
Henri de Toulouse-Lautrec 1893 Monsieur Boileau at the Cafe
Pablo Picasso 1901 Harlequin and his Companion
Pablo Picasso 1901 The Poet Cornuty
Pablo Picasso 1901 The Absinthe Drinker
Pablo Picasso 1902 The Absinthe Drinker
Pablo Picasso 1911 Glass of Absinthe
Pablo Picasso 1914 Absinthe Glass

References

1. Baggott, Matthew. Absinthe. 1997. http://itsa.ucsf.edu/~mbagg/roughabsinthefaq.html

2. Arnold, Wilfred Neils. Absinthe. Scientific American 260.6 (1989): 3042-4.

3. Budavari, Susan, ed. The Merck Index, 12th edition. Whitehouse Station, NJ: Merck & Co., 1996: p.(a)3,(b)1603.

4. Summary of Data for Chemical Selection: Alpha-Thujone (546-80-5). http://ntp-server.niehs.nih.gov/htdocs/Chem_Background/ExecSumm/Thujone.html

5. Rice, K.C; Wilson, R.S. (-)-3-Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice. Journal of Medicinal Chemistry 19.8 (1976): 1054-7.

6. Del Castillo, J; Anderson, M; Rubottom, GM. Marijuana, absinthe, and the central nervous system. Nature 253 (1975): 365-6.

7. Meschler, J; Marsh, C; Land, B; Howlett. Failure of the active component of absinthe (Artmisia absinthium) to bind the cannabinoid receptor. International Cannabinoid Research Society, 1997 Meeting.

8. Hold, K; Sirisoma, N; Ikeda, T; Narahashi, T; Casida, J: a-Thujone (the active component of absinthe): g-Aminobutyric acid type A receptor modulation and metabolic detoxification. PNAS 97.8 (2000): 3826-31.

9. Absinthe & Thujone. http://www.chem.ox.ac.uk/mom/absinthe/absinthe.html

10. Prisinazano, Thomas. Thujone. 1997. http://www.phc.vcu.edu/feature/thuj/thujone.html

11. Wu, C. Toxin in absinthe makes neurons run wild. Science News 157.14 (2000): 214.
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Hippie3 (Admin)
Posted on Monday, August 18, 2003 - 02:17 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

archive material

from http://chemweb.calpoly.edu/chem/bailey/377/PapersSp2000/Ann/absinthe.html
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Erebus (Debremus)
Posted on Monday, August 18, 2003 - 02:43 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

I made my own halfassed absinthe a few months ago. Fresh wormwood (available at local nursery) was chopped and steeped in absolut vodka for 2 weeks, resulting in a beautifully green liquid. An undetermined amount was used, but I used a whole plant about a foot high, not bushy looking like that pic. It tasted like crap. It smelled divine.

The only effects I may have felt were of course alcohol intoxication with a slight hint of some energy and maybe a little increased creativity, but I attribute these to placebo.

Im guessing any effects received from absinthe are fairly mild. I'm also guessing absinthism is due to the chronic use of alcohol. Alcoholics get the same effects from withdrawals. Of course I am no authority on this these are merely speculations.

Good read!
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Roc (Rochester)
Posted on Monday, August 18, 2003 - 04:15 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

Thanks for sharin

Roc
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Soliver (Soliver)
Posted on Monday, August 18, 2003 - 10:48 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

Absinthe has great history and nostalgic appeal.
But as for it's "drug" uses, I've found it, and
wormwood, to be more or less a dissapointment.

Still, gotta love it for it's past, maybe we can
enjoy it in the present too - just don't expect
any mind-rocking alterations . . .

sol
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Erebus (Debremus)
Posted on Tuesday, August 19, 2003 - 12:03 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

It seems to me like absinthe was to the 1800's what acid and psilocybian mushrooms were to the 60's and 70's.

Can you imagine a time before anyone knew about hallucinogens, or at least most everyone didn't know about it? Thats crazy, no wonder why everyone was so straight and all preppy looking haha. These substances truely defined who we are, or at least the art culture. So very important yet so very illegal, how interesting.
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Hippie3 (Admin)
Posted on Tuesday, August 19, 2003 - 12:08 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

evidence that a little knowledge can be dangerous.

Quote:

In a recent case, a male subject drank about 10 ml of essential oil of wormwood under the impression that it was in fact absinthe which he had learned of on the Internet/World Wide Web. He was found several hours later agitated, incoherent, and disoriented. He improved with treatment but subsequently acute renal failure developed (Reese, 1997).



from http://ntp-server.niehs.nih.gov/htdocs/Chem_Background/ExecSumm/Thujone.html
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Blodwen_1 (Blodwen_1)
Posted on Tuesday, August 19, 2003 - 01:47 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

I've seen the other absinthe post, and read everyones comment, seems like quite a few people are right on, Hippie, Solver.
The post about a person drinking 10 ml of essential oil and getting renal/kidney failure, definately could happen in my opinion. Smells like estringent, always gives me a case of the smellys. Spewing is rather interesting, even after using wormwood oil, it comes up in a green solid mass (on a fairly empty stomach).
The recipies I believe you want are for Pernot, and the other famous brands. I've caught a few, but unless you distil, the stuff will be bloody awful.

I wouldn't waste my money ordering any bottle online, besides being troublesome, for the most part you'll get the fake stuff, and it'll be pricey. The key places to visit would be France, England, Amsterdam, and Spain, Sweden, and Bulgaria.
The fun is in experimenting with the recipies to you're personal taste. When soaking the ingredients with no distillation it will take more anise oil to make it cloudy, and therefore more foul tasting.

"Absinthe has great history and nostalgic appeal." -Soliver. And it's probably one of the best things about the drug, the artwork is beautiful. In the 1800's, it was one of the only alcoholic drink proper women would drink in public.
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Hippie3 (Admin)
Posted on Thursday, September 04, 2003 - 02:06 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

drinking many 'essential oils'
can be very risky health-wise.
one best do their homework first.
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Blodwen_1 (Blodwen_1)
Posted on Friday, September 05, 2003 - 05:04 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

I just say no to Absinthe these days, can you expand on you're health risk issues, and digesting essential oils? I always went up in medium-small increments, I really feal Absinthe affects the kidneys or liver, and from what I've read the tongue. I haven't had the tongue experience, I'll stick with the MJ as always. However I did purchase a nice piece of artwork recently.
titus

blood
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Hippie3 (Admin)
Posted on Friday, September 05, 2003 - 03:48 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

several herbs that are relatively benign in normal concentrations become much more toxic when concentrated into essential oils.
so one had better know which herbs are safe,
and which ones aren't.
in general i'd avoid any essential oil for consumption unless it's been vouch-safed by others.
nice pic.
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Voodoo (Voodoo)
Posted on Saturday, September 06, 2003 - 01:30 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

It only affects your tongue if you bite it in your sleep. LOL
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Hippie3 (Admin)
Posted on Sunday, September 07, 2003 - 11:09 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)


lol
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ShroomVator (Shroomvator)
Posted on Tuesday, October 29, 2002 - 01:11 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

From Erowid:

30.0 g wormwood
8.5 g hyssop
1.8 g calamis
6.0 g melissa
30.0 g anise seed
25.0 g fennel seed
10.0 g star anise
3.2 g coriander seed

Put the dry herbs in a large jar. Dampen slightly. Add 800 ml of 85-95 percent alchohol. Wine spirits make a better product than pure grain alcohol. Let it steep for several days - a week is better - shaking occasionally. Then add 600 ml of water and let the whole macerate for another day. Decant off the liquid squeezing as much from the mass of herb as possible. Wet the herbs with some vodka and squeeze again. Recipe should give a little over a liter and a half of green liquor. It must then be distilled. Inferior recipes skip this step, but what they produce is not worthy to be called absinthe.

In the distillation, change the receiver when the distillate turns yellow: those ar the faints. You can save the faints and add them to future distillations, but they will taint the flavor if added directly to the product. Just use the good stuff. The next step is to color and finish the liqueur by another round of maceration.

Color the distillate by again adding:

4.2 g mint
1.1 g melissa
3.0 g wormwood
1.0 g citron peel
4.2 g liquorice root

Let the herbs macerate for another three or four days. Decant, filter, bottle. You will probably want to carefully add some concentrated sugar syrup to the blend. The result will be a Swiss style absinthe of about 135 proof.Recipe makes one liter of absinthe.
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ShroomVator (Shroomvator)
Posted on Tuesday, October 29, 2002 - 01:16 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

Actually, heres a link to a page all about Brewing, Mixing, and Serving Absinthe. This has it all.

Great Absinthe Site

I know the easy way is to mix absinthe extract with pernod.

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Hippie3 (Admin)
Posted on Tuesday, October 29, 2002 - 01:31 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

damn, we used to have some great stuff in the archives on absinthe, great pics, too.
guess it's in the 10,000 post archive which we no longer have online.
let'se see if i can find those pics...
absinthe
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Blodwen_1 (Blodwen_1)
Posted on Saturday, July 26, 2003 - 02:33 pm:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

I have some experience in this area. I've experimented with Artemisia annua with little success.

There are three parts to making proper absinthe. Distillation, getting the proper technique for taste and the recipe.

Like everyone mentions the effects are alcohol like. I think the most important ingredients in Absinthe are Calamus Root, and wormwood oil. I never picked up effects as much until I played with amounts, slowly upping them until you're tolerance level.
The stuff tastes like spiked liquid Nyquil/vodka if undistilled. I always felt the effects were similar to crushing codeine in vodka. The recipe can be tweaked to you're tastes with the same effects, I've always felt the other ingredients had little noticeable effect, except to the taste buds. Always gave me stomach discomfort, and a few other issues.

Here is the vendor I went to at first for extract, but only once. http://basementshaman.com/arabexwor.html
The Hippie3 steam extraction method will do the job nicely. Should you decide to pursue it. You can always add extract to the non distillation way with noticeable effects.
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Jason (Natureboy)
Posted on Thursday, August 21, 2003 - 12:08 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

The original Pernod recipe calls for two types of wormwood, common Ar. absinthum and roman of which I forget the latin. Common is so easy to grow and so hardy that I would suggest investing in a live plant, stem cuts easily for propagation, Many of the other herbs like mellissa (lemon Balm) are also easy to grow. The roman wormwood is easy to grow but is a small plant. No choice though if you want to be authentic. I suggest growing it I doubt you could find roman wormwood herb for sale. As far as the other herbs if you aren't interested in growing, check out atlanticspicecompany.com, if that url isn't kosher search for Atlantic Spice Company. They have an extesive list of botanicals in bulk quantities for next to nothing, I am taiking like $3-$4 LB. Good luck, Pernod also used distilled wine spirits not vodka or grain alcohol. Natureboy
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Admin (Admin)
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Posted on Tuesday, February 10, 2004 - 03:36 am:Edit Post Quote Text Delete Post Print Post Move Post (Moderator/Admin Only)

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