Effects - Difference in effects of absinthe constituents (thujone/anethole/estragole/fenchone)

Discussion in 'Ethnobotanicals' started by DextromethorFan, Sep 16, 2012.

  1. DextromethorFan

    DextromethorFan Silver Member

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    Traditional absinthe uses wormwood (contains thujone), anise (contains anethole/estragole) and fennel (contains anethole/ fenchone/estragole). Bohemian absinthe uses only wormwood, and thus contains only thujone.

    Dex reads that the thujone content in vintage absinthe, which is said to be relatively high in comparison to contemporary brews, is what causes the hallucinations noted by drinkers of the concoction. His intuition leads him to believe this to be true; Else, why would they regulate thujone content to such low, sub-psychoactive amounts (besides the fact that rather large doses can cause convulsions and death) and not the other compounds?

    He reads of extracted thujone imparting a state of creativty, clear-mind, and euphoria/ body-drunkness and attributes this to its GABA antagonism, though has not found anything declaring anethole's psychoactivity save for limited CNS stimulation. Likewise, fenchone/estragole has little effect unless the latter is combined with an enzyme inhibitor, namely german chamomile.

    Dex wants to know:

    1) Has anyone dreamed of trying pure thujone, anethole, fenchone, or estragole (also known as methyl chavicol), and can attest to any difference in effects between them without the use of any enzyme inhibitors that would otherwise not be in absinthe.

    2) If not, have they dreamed of drinking traditional/bohemian absinthe of similar alcohol content (and without the admixture of other herbs) and noted any difference?

    3) Do these constituents react with one-another to create the absinthe hallucinations, or is a single chemical (thujone) actually responsible for the phenomenon? (for example, if any of them inhibit CYP1A2 then they could potentiate the estragole and cause psychedelia)...

    Thanks!

    EDIT: Dex reads that estragole by itself has little-to-no effects..
     
    Last edited: Sep 16, 2012
  2. PowerfulMedicine

    PowerfulMedicine Silver Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    Methyl chavicol, or estragole as you refer to it, is psychoactive on its own. From my unsuccessful experiences trying to use methyl chavicol in oilahuasca mixtures, I would describe it as being a mild to moderate sedative with a trippy aspect to it. The effects are sub-psychedelic like the beginning of an actual trip that never materializes. It is somewhat like cannabis but milder.

    I can feel the effects of .8mL of sweet basil essential oil which is about 70% methyl chavicol. The effects are far more pronounced at 3mL. These doses are probably higher than many people will need to feel the effects.

    It is also interesting to note that methyl chavicol has been successfully used by some people as its own enzyme inhibitor. So a large enough dose of absinthe may be able cause hallucinations based on the methyl chavicol content alone.

    Some people have noted the development of a reverse tolerance to methyl chavicol with regular and frequent use, possibly related to chronic lowering of the enzymes that deactivate it. So if a person were to regularly drink absinthe, then they would be more likely to experience hallucinations.

    It should also be noted that some people have used anethole rich oils like anise and star anise essential oils as a predose for methyl chavicol to successfully activate it. And regular frequent use of anethole rich oils has also caused a reverse tolerance to methyl chavicol in some people.

    So, the mixture of anethole and methyl chavicol without the thujone could be the cause of absinthe hallucinations. But I would guess that thujone probably does play some role in the hallucinations. And I am not sure of the concentrations of anethole and methyl chavicol in absinthe, so for all I know absinthe may not contain sufficient amounts of these compounds for them to be the main cause for the hallucinations.
     
  3. rawbeer

    rawbeer Gold Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    I have drank high thujone, homemade absinthe which has a strong effect. It is not hallucinogenic or psychedelic but it effects vision and makes light/ shadow interplay much more interesting than usual. It is a clear, lucid, colorful experience.

    I have drank anethole-heavy drinks like sambuca, raki, ouzo and pastis and the effect is in no way similar.

    I have also had a homemade wormwood liquor. Same amount of wormwood as absinthe but with no other ingredients but wormwood and liquor. The effect is nearly identical to absinthe. So if the anethole/ fenchone has any added effect to absinthe it is subtle.

    I personally think the other herbs used in absinthe are mainly flavoring agents and that wormwood is the main active ingedient. The effects that anethole and fenchone and the other oils in absinthe add don't really alter the experience that much. The absinthe effect is mainly wormwood and alcohol.

    Alcohol does seem to potentiate the effect, If you drink good absinthe and go on to drink normal alcoholic drinks like beer they will to some extent potentiate the effects.
     
  4. DextromethorFan

    DextromethorFan Silver Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    PowerfulMedicine, thank you for this insight. Perhaps the absinthe-drinkers of yesteryear experienced these supposed "hallucinations" due to drinking large amounts and/or drinking the spirit for extended periods of time, effectively overwhelming and/or depleting the enzyme by which the oleochems are metabolized. And what you said about predosing an estragole experience with anethole oils leads me to believe there is some interaction between them; perhaps they inhibit or compete for the same enzyme (P450 if not mistaken).

    And Rawbeer, having read many of your posts about absinthe, I had hoped you would chime in. Getting right to business, you say thujone-heavy absinthe causes a colorful experience... how so? Colors are brighter? What concentration of thujone was present? Was there any increase in creativity as noted by imbibers of the spirit during the Belle Epoque? Also, what effects did the anethole spirits impart, if any (besides those of ethanol)?

    Currently, Dex is convinced that known associates of the green fairy experienced visions due to excess/extended consumption of the brew, possibly causing the oleochems -- most notably estragole (as it seems to be the only one to be a known psychedelic) -- to induce the hallucinations. Perhaps interactions between the oleochems increased the likelihood that the phenomenon occurred (anethole inhibiting the enzyme estragole is metabolized by, causing its psychedelia to become pronounced) or possibly the said enzyme simply became saturated and the surplus, unmetabolized estragole caused the effects.

    Though, he believes thujone cannot be ruled out [of causing hallucinations] either. But, as Rawbeer's experience suggests, the ketone causes a lucid/clear state versus a psychedelic one.

    Dex currently has an 'absinthe' that he personally made, which would most-accurately be described as dead leaf bohemian absinthe (an allusion to its oxidized chlorophyll content and absence of anise/fennel) which he made from soaking 1 ounce (~33g) of fresh sage (Salvia officinalis) in roughly 4 shots (8oz) of 40% ABV spiced rum for 5 days. During the filtration, an additional 8oz of water was used to ensure complete extraction of the thujone-alcohol. The end product was roughly 16oz of 20% ABV brown liquid with a pungent taste and smell that had approximately 20mg thujone/fluid ounce (assuming that yields were quantitative and there is a thujone content of 35% in the oils with an average oil content of 1.7%, meaning 595mg per 100g of sage, or 166mg within the ounce used), though it was more likely to be 10mg/oz.

    He consumed 2oz alongside 8oz of muchomango, which made the taste manageable. A warmth came along as per usual with alcohol. Ten minutes elapsed before an equal drink was consumed and with it came a sense of well being, appreciation for music, pinpoint pupils, and [slight] mental/visual clarity that would otherwise not be present with an equivalent dose of alcohol (one 40% ABV shot). Though, his experiment ended there as he had to drive to work in the near future. He will continue his assay of the brew sometime soon.



    On a side note, Dex believes absinthe suffered a similar fate as that of marijuana, both whose primary actives -- thujone and THC, respectively -- are, coincidentally, said to be similar in molecular structure. Both were a large part of culture at some time (weed with the 60s/70s USA and absinthe with the Belle Epoque France), and both were eventually banned following a frenzied series of misconceptions and skewed/exaggerated articles and medical studies involving very large doses on small animals and the subsequent effects. Both bans, in his opinion, were works of each nation's respective governments wanting to suppress these substances which were used to inspire creativity and abstract thought that conflicted with their own ideas. Does reefer madness and absinthism ring a bell?
     
    Last edited: Sep 20, 2012
  5. rawbeer

    rawbeer Gold Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    Absinthe has a powerful effect on vision that is somewhat hard to describe. I think it is appropriate that absinthe was traditionally consumed in the late afternoon as the sun is getting lower in the sky because absinthe makes the interplay of light and shadow simply amazing to behold. It somehow strengthens the contrast and gives it more depth. Whereas looking at a garden bathed in sunlight while drinking absinthe is nice, looking at that same garden with shadow creeping over it is much better. Sunlight passing through shrubs and trees is spectacular.

    Absinthe also has some sort of subtle effect on depth perception. For example reading text after drinking absinthe has the appearance not of a flat page or screen, it seems the letters are floating and in general the page/ screen seems to have depth to it.

    Colorful was perhaps a bad choice of words...I meant it figuratively more than literally. But absinthe in general makes anything more interesting too look at. I tend to drink it outside in my garden and so I associate it with that environment. But really the dominant visual effect has to do with light and shadow. It makes everything brighter.

    I couldn't say about creativity...I personally find it very difficult to do much while drinking absinthe! Mainly you just want to stare off. There is stimulation in the head, a general tightness in the upper shoulders, forehead, back of the head and around the eyes, which is pleasant. When one stares off in absinthe revery a tingly rush often passes through the head, as if the wonderful visual effects are caressing your brain. There's a definite dreamy quality too.

    This aspect of absinthe is he hardest for me to describe - it's stimulating but dreamy. It forces you to stare at nothing. It's like unfocused stimulation, or intensely focused sedation. It's similar to marijuana in some ways although I really want to stress that it doesn't feel very much like pot at all. It's not as euphoric and has much less mental effect, no giggles, no wierd thoughts. However it can be somewhat antisocial like pot because of the tendency to revery.

    I can't say for sure what the thujone content of the absinthe is. It's based on Dale Pendell's recipe in Pharmako/Poeia which he estimates at 45mg thujone/ liter. I used a little more wormwood than his recipe calls for so I'd say at least that much.

    (I would also like to note that the effects of absinthe come on quite quickly, within a few sips. You're there by a quarter glass. The more you drink the dreamier it gets and the harder it gets to think. I've been drinking it quite often lately, partly to test the theory that it builds up in the system. If and when I come to any conclusions about that I'll let everyone know.)

    Straight wormwood booze is less dreamy, but the visual effects and tightness are there. A lot of the dreaminess seems to come from the other herbs.

    I have noticed that the more I drink absinthe the more I crave the flavor of anise. I actually had to go buy a bottle of pastis to satisfy my cravings or else I would go through my supply of absinthe too quickly. I would catch feint wiffs of anise-smell (I think maybe from dog fennel, a common weed in my area) on the breeze and salivate. Normally I like anise allright but I'm not that nuts over it. I bought Henri Bardouin pastis which is great, a very complex spicy drink. However I notice no absinthe like effects at all from it, just a wonderful taste. But the anise cravings are unusual and strong.
     
  6. DextromethorFan

    DextromethorFan Silver Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    Wonderful reply, answered what I needed to the best of your abilities. You say the thujone content of the homebrew was roughly 45mg+ per liter, or about 3mg per shot's-worth (2oz, 66fl oz). Though likely strong compared to other available selections, it would still take a substantial amount of liquor to reach a substantial amount of wormwood. How many fl oz did one drink?

    And perhaps the connection between the extreme need to indulge in anise is linked to the chemicals within?
     
  7. rawbeer

    rawbeer Gold Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    .5 oz is enough to feel effects. I usually drink between 1-5 oz, 1oz per glass. The batches have varied from 67-75% alcohol so I try to take it easy.

    From what I've read about thujone this amount of absinthe shouldn't have any pharmacological effects attributable to thujone. But it's clearly something in the wormwood doing what it does. It's not just that alcohol potentiates it because one study I read had people consuming a thujone/ ethanol drink to rate their responses, which were negative (nothing happened except with quantities of thujone far too high to obtain from drinking absinthe). It's not really that the other herbs potentiate it because if they're removed the central effect is still there.

    I suspect perhaps some other chemical in wormwood is responsible. But then a lot of modern absinthes claim to use a full measure of wormwood and yet do not contain the full measure of thujone (45mg/L) which would be illegal (how they do this is beyond me. Perhaps a low-thujone strain of wormwood? Wormwood loses its potency if it's not very fresh too, maybe they just use old stuff?) If it's some other un-regulated chemical, store bought absinthe should be active, which it isn't.

    The study regarding people drinking thujone/ ethanol concoctions rated their attention performance in a clinical environment. I'm not so sure that's going to be very revealing. I can focus and perform any sort of normal task while drinking absinthe (I won't drive because of the ethanol). I want to drift off but I don't have to. It's comparable to a small amount of cannabis for me, like one puff. I can focus on the high or I can do anything I could normally do without the high hindering me.

    I think a good test would be for people to rate images while intoxicated on absinthe. I bet images with heavy interplay of light and shadow would be preferred to images with more uniform light exposure. But rating pictures in terms of pleasantness is already getting into uncomfortable grounds for science...

    There are still a lot of good questions about absinthe and its constituents that need to be answered, hopefully this thread can do some help! I'm glad you started it. I find these topics very interesting, however sometimes I'm just too busy enjoying my absinthe to bother about why it's doing what it's doing!

    I've heard DF member Yail Bloor may have had some pretty good luck with absinthe...ya hear me Yail? Care to chime in?

    Here's the study I was mentioning. Just google it, I'd rather not post a link.

    Absinthe: Attention Performance and Mood under the Influence of Thujone


    A. Dettling, H. Grass, A. Schuff, G. Skopp, P. Strohbeck-Kuehner, H.-Th. Haffner
     
  8. PowerfulMedicine

    PowerfulMedicine Silver Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    The theory behind predosing with anethole to activate methylchavicol is based on the similarity of these compounds. Methylchavicol is an allylbenzene while anethole is a propenylbenzene. The only difference between these two chemicals is the position of the double bond in the tail.

    In anethole, the double bond is in the center of the tail as opposed to the end. This makes it less reactive and prevents it from being metabolized into the aldehyde version of the molecule. This step is believed to be necessary in order to from the psychedelic metabolite and this is why anethole is not psychedelic.

    The similarity of these compounds means that they should be metabolized in nearly the same way. Anethole has been found to inhibit generally the same major Cytochrome P450 enzymes as methylchavicol in scientific studies. But research on the metabolism of these compounds is limited, so its effects on other enzymes are unknown.

    What do you mean by wormwood? Artemisia vulgaris or Artemisia absinthium?

    I have a whole bunch of A. vulgaris that I recently picked and I was planning on using some to make a sort of "absinthe" and was wondering how it would compare to absinthe made using A. absinthium.

    Perhaps the dreamy effect is from methylchavicol. I have definitely noticed a dreamy sort of effect from this compound.
     
  9. rawbeer

    rawbeer Gold Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    By wormwood I mean A. absinthium. I've thought many times about using A. vulgaris, mainly as sub for A. pontica in the coloring step of absinthe making, but I've never gotten around to it. My next batch I may use it. It's defintiely less bitter - I've eaten both absinthium and vulgaris and vulgaris is palatable, absinthium not (at all!) You may be able to use it without distilling. I don't know how the effects would compare...

    I actually was ready to use vulgaris (which I know as Mugwort) but I realized I had picked Ambrosia (ragweed) by accident! They look prety similar.

    I need to go buy more pastis and compare it to absinthe...methycavicol does seem like a good candidate for the dreamy effects. When I drink pastis I tend to just drink it with little regard to "bioassaying" the effects but this thread has gotten me curious.
     
  10. DextromethorFan

    DextromethorFan Silver Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    Dex ingested 4 shots of his homemade sage "absinthe" (20% ABV, basically 2 shots of regular liquor) and felt a pleasant uplift/ pinpoint pupils/ slight euphoria/ clarity that had a noticeable difference from alcohol alone (2 shots would do nothing normally). He is unsure if common sage has the same chemical makeup as wormwood, though he doubts it. This seems to disprove the above quote, perhaps?
     
  11. usernamefield

    usernamefield Newbie

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    this was written on a bottle of absinthe i afoaf found in a river:

    Alpha-thujone is a moderate strength CYP2A6 inhibitor

    fennel contains L-lysine, limonene, anethole
    -Limonene inhibits CYP2A6 strongly, induces CYP2C9
    -anethole induces CYP2C9
    -L-lysine is broken down into piperidine by the stomach takes ~1 hour, this is likely why its best to take a shot every15-30 minutes for 1-2 hours to get the effects to show themselves

    artimisia species contain CYP2C9 inducers

    the sugar (glycerin) is a weak aldehyde dehydrogenase inhibitor

    the ethanol is a weak alcohol dehydrogenase inhibitor, weak enough to flick the enzyme and quickly it recovers in fact the second and further shots alcohol dehydrogenase would become tolerant to inhibition via ethanol and would reverse into induction.

    the only thing i see missing witch is likely from not digging enough is CYP2D6 and CYP1A2 inhibition, other than that the 3 herbs make a very decent methyl chavicol activator.
     
  12. usernamefield

    usernamefield Newbie

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    all according to afoaf's recollection of the bottles writing
     
  13. 69Ron

    69Ron Titanium Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    I think absinthe was the very first "Oilahuasca". It appears that enzyme inhibition was probably the key to successful effects from it.

    During its heyday absinthe was controversial though. It wasn't made well enough to work in everyone. It was said to work great in some people but was said to be just like regular alcohol for others. There was a lot of skepticism surrounding it, just as there is with elemicin, myristicin, etc.

    Also, I think some of the original historical data on its active ingredients was likely corrupted by the marketplace of that time period. It's been the case that during the heyday of absinthe that some portion of the herbs and essential oils being sold were not always the real deal. Sellers would sell similar oils as popular in demand oils to get a higher price for them. Oils like fennel and basil would be mixed together and sold as pure fennel oil to the unsuspecting. Some herbs were also sold like this. This kind of practice still occurs today, but is much less frequent because ingredients can be tested more readily these days.
     
  14. rawbeer

    rawbeer Gold Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    ^^^ With all due respect I do not agree. If enzyme inhibition was the key, why would absinthe work on the first glass? Wouldn't several be necessary? Absinthe takes effect very quickly, in only a few minutes.

    Or perhaps you mean that only some people will get effects...but I don't really agree there either. I've given homemade absinthe (properly distilled, well made) to a few people and it works on everyone. It's just that some people aren't very good at detecting subtle highs. Even the people who didn't seem to think it was doing much got effects from it. They just didn't seem to think much of those effects. This phenomenon is true with any drug - some people just don't "get" it.

    I do agree with your comments about adulterated herbs and oils fully. If you look at chemical analysis of vintage absinthes you'll see that their thujone content varies widely - from nearly 50mg/L to almost nothing, even for the same brand, Pernod Fils. The bottles analyzed have been from the end of absinthe's heyday - post 1895. One would assume the demand for absinthe herbs was sky high by this point and low quality or fraudulent herbs led to inconsistencies in the product, hence inconsistencies in the same brand even, and one of the most highly regarded.

    Absinthe's effects are subtle and are attributable almost entirely to wormwood, in my experience. I have written an extensive series of posts on it in my thread here:

    https://drugs-forum.com/threads/169904?highlight=absinthe

    So I won't repeat myself, read if you're interested.

    The mystery of absinthe comes from a combination of many historical factors - adulterated herbs during the Belle Epoque, anti-absinthe hysteria, hyperbolic artists and writers taking considerable poetic license in describing the effects (and there is a confusion of personal reflections with pharmacological effects in modern readings of these accounts - because a man imagined tigers after drinking absinthe doesn't mean the absinthe made him see tigers) and finally the modern absinthe "revival" that is much more concerned with making $$$$ than telling the historical truth.

    I am currently sipping a glass of absinthe made in strict accordance with an 1855 recipe. I usually add extra wormwood, as well as some fresh wormwood and other stuff but this is straight-up 1855 style Absinthe of Pontarlier. The wormwood was grown in my garden, was totally dry but freshly so, only a few weeks after I harvested it. It has the same effects as my other homemade batches have had, although decidedly less pronounced (which isn't bad actually - my last batch was pretty stupefying and I don't like feeling stupid). No modern mass-produced absinthe has given me these effects - a couple have done something interesting but the real absinthe high is unmistakable and is not present in legal modern absinthe.

    The problem is not entirely solved but I really believe it is the wormwood, it must be quality. Pastis doesn't have the effect but a plain wormwood liquor does. But is it thujone? Who knows? But modern absinthe has unhistorically low thujone levels and an unhistorical lack of effect. I think it is made with very old wormwood, or someone has somehow figured out how to otherwise limit it (low-thujone strains? Ted Breaux's assertion that thujone "stays in the pot" during distillation is a flat-out lie).

    Once I've tried more of the 1855 recipe stuff, and more of my wormwood liquor that isn't ready yet I'll add my observations to the absinthe thread I started. I really think I'm pretty close to sticking a fork in this whole issue, and I have nothing to gain from it but reputation points on this site so why would I be making this stuff up? I don't need to lie for good rep.

    When it's all said and done I want to send all my research off to Ted Breaux and see if he'll respond. The guy's apparently a serious chemist and absinthe fan. But I think above all he's a serious businessman. In the meantime I would advise anyone who wants absinthe to not waste their money on store bought stuff. Make it yourself or buy Chartreuse, modern absinthe is a scam.
     
  15. abigail48

    abigail48 Mercury Member

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    Re: Difference in effects of absinthe constituents (thujone/anethole/estragole/fencho

    rawbeer: there are apparently 180 varieties of artemesia, & it grows wild in the western us