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Ethnobotanicals Psychedelic plants, Iboga, Calea, Blue lotus, Ephedra, Sinicuichi, Betel nut, etc.

 
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  #1  
Old 24-12-2010, 16:57
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an exploration of methyl chavicol

Afoaf has been experimenting with psychoactive essential oils lately and here is some info he has found on Methyl Chavicol

Origionally posted by Ron69 on another forum.

Quote:
The Psychoactive Effects of Sweet Basil Oil



There are two varieties of sweet basil essential oil. The useful psychoactive chemotype (abbreviated as ct usually) is high in methyl chavicol (estragole, para-methoxyallyl benzene), and the other variety is high in linalool. When buying sweet basil essential oil, the chemotype is usually listed. The two smell and taste quite different. The methyl chavicol chemotype is usually the preferred chemotype for aromatherapy.



Some sweet basil contains as much as 85% methyl chavicol.



I’ve ingested up to 10 drops of sweet basil oil containing about 70% methyl chavicol. The effects start in about 30 minutes and seem to peak after 90 minutes. Overall the effects last a few hours. It’s mild at that dose. It’s relaxing, mildly euphoric, and mildly psychedelic. Did I type “psychedelic”? Yes, that’s right, at 10 drops for me it is mildly psychedelic. I experienced very mild visuals from it at that dose. This is actually not too surprising. Methyl chavicol (para-methoxyallyl benzene) is very closely related to PMA (also known as para-methoxyamphetamine, 4-methoxyamphetamine, or 4-MA) which is a known psychedelic amphetamine sometimes sold as MDMA.



Apparently methyl chavicol, like elemicin, is metabolized by CYP1A2. With elemicin, it was found that 5+ grams of German chamomile (a potent CYP1A2 inhibitor) greatly potentiates the effects of elemicin, making it both stronger and more psychedelic. It’s possible that German chamomile might have a similar affect with methyl chavicol.



Methyl chavicol doesn’t appear to be very toxic. Here is some LD50 data I found on it:



Oral-Rat 1230 mg/kg

Intraperitoneal-Rat: 1030 mg/kg

Oral-Mouse: 1250 mg/kg

Intraperitoneal-Mouse: 1260 mg/kg



Sweet basil oil is on the US FDA GRAS list, meaning its safe to use as a food flavoring. It’s also not very toxic:



Oral-Rat: 1400 mg/kg



Be careful using basil for psychoactive purposes. As of yet, I know of no one else who’s used it for this purpose. There is very little information out there on its use as a psychoactive. However, people eat basil all the time all around the world, so we know that low doses of methyl chavicol are apparently safe.



Note that there seems to be cross tolerance between the psychedelic effects of elemicin and methyl chavicol, and probably myristicin.
Some info on possible toxicity from wikipedia.

Quote:
Estragole (methyl chavicol) is suspected to be carcinogenic and genotoxic, as is indicated by a report of the European Union, Committee on Herbal Medicinal Products[2]. Several studies have clearly established that the profiles of metabolism, metabolic activation, and covalent binding are dose dependent and that the relative importance diminishes markedly at low levels of exposure (i.e. these events are not linear with respect to dose). In particular, rodent studies show that these events are minimal probably in the dose range of 1-10 mg/kg body weight, which is approximately 100-1000 times the anticipated human exposure to this substance. For these reasons it is concluded that the present exposure to estragole resulting from consumption of herbal medicinal products (short time use in adults at recommended posology) does not pose a significant cancer risk. In the meantime exposure of estragole to sensitive groups such as young children, pregnant and breastfeeding women should be minimized. The Scientific Committee on Food from the Health & Consumer Protection Directorate-General took a more concerned position and concluded that "Estragole has been demonstrated to be genotoxic and carcinogenic. Therefore the existence of a threshold cannot be assumed and the Committee could not establish a safe exposure limit. Consequently, reductions in exposure and restrictions in use levels are indicated.[3]
Terragon oil and sweet basil oil are high in methyl chavicol

Experiences with german Terragon oil (also contains M chavicol.)

Test 1-no german chamomile used.

not really all that remarkable, used 10 drops, experienced slight sedation and very little psychedelic activity, at one point afoaf thought colors where hightened but it was likely placebo.

Afoafs experiences with Sweet basil oil.

Test 1- no german chamomile used

Again just mild sedation, no real psychedelic properties, was even milder than the terragon oil, will attempt to potentiate with chamomile.

Test 2- 5g german chamomile used

There we go, experienced mild CEVs (mainly faint patterns, Colors hightened, mild euphoria, as well as an increased appreciation for music, sedative effects are not really pronounced this time, no obvious OEVs noticed, however there was a very slight breathing of the walls in afoaf bedroom.

will retry the terragon oil with german chamomile


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Extremely interesting and thorough thread!
Good job! Thanks for sharing your research.
  #2  
Old 13-01-2011, 21:52
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

Quote:
Originally Posted by phenythylamine View Post
Test 2- 5g german chamomile used

There we go, experienced mild CEVs (mainly faint patterns, Colors hightened, mild euphoria, as well as an increased appreciation for music, sedative effects are not really pronounced this time, no obvious OEVs noticed, however there was a very slight breathing of the walls in afoaf bedroom.

will retry the terragon oil with german chamomile
Was this test repeated at a stronger dose?

SWIM tried using basil oil (c.t. methyl chavicol) with German chamomile, but this was after using elemicin/isoelemicin. It altered the experience very slightly. I think there is cross tolerance between elemicin and methyl chavicol.

Note that methyl chavicol has an isomer called anethol which often occurs along with methyl chavicol. I have reason to believe that its the stronger isomer of the two. Some plants containing high amounts of anethol are alleged to be psychoactive, while plants containing a large amount of methyl chavicol are not generally known to be psychoactive (that doesn’t mean they aren’t though, basil oil is clearly psychoactive).

I’m thinking that possibly the psychoactive effects from basil oil are primarily from the anethol content and that the methyl chavicol (its isomer) is maybe potentiating it but that the methyl chavicol on its own doesn’t really do much.
  #3  
Old 14-01-2011, 21:05
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Re: an exploration of methyl chavicol

afoaf is repeating these tests tonight, well let you all know how it goes, does anyone have a TEK to isolate anethol.
  #4  
Old 15-01-2011, 06:24
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Re: an exploration of methyl chavicol

Anethol? That reminds me of isoelemicin. Anethol has the same kind of relationship to estragole, which is a suspected carcinogen. What kind of research regarding safety of all of these compounds is out there?

Additionally, since these are readily available and double bonds are reactive, what is the possibility of using these as precursors?
  #5  
Old 15-01-2011, 11:06
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

Quote:
Originally Posted by Jasim View Post
Anethol? That reminds me of isoelemicin. Anethol has the same kind of relationship to estragole, which is a suspected carcinogen. What kind of research regarding safety of all of these compounds is out there?


None of these suspected carcinogens, even the notorious safrole, have ever been shown to actually cause cancer in humans. Their human carcinogenicity is theoretical based on lab tests with rats using very large doses of isolated compounds. Myristicin has been shown to help PREVENT cancer, but also shown to cause it. It all depends on the tests used. Basil oil, from what I've read, is not considered carcinogenic because it apparently contains compounds that counteract the potential carcinogenicity of methyl chavicol. It's considered GRAS in the USA, meaning it's safe to use in food, and not a listed carcinogen. I eat basil a lot and I don't have cancer.

By the way, German chamomile greatly reduces the possible carcinogenicity of these compounds by interfering with CYP1A2 metabolism, which is the main cause of their potential carcinogenicity in the first place. So not only does it make them more effective it also reduces the possible carcinogenicity these compounds might have at extremely large doses.

Keep in mind that lab tests showing carcinogenicity do not generally use whole oil, but isolates, and in huge amounts fed to the animals continuously day after day. Humans do not use these oils or their isolates in that way. They take small amounts, and only on occasions, not every day all day for weeks at a time.

I'm sure if all I ate was basil oil all day for weeks I would get sick. I'm sure also, if all I did was drink coffee all day I would also get sick. You need a proper diet to be healthy. Often times in lab tests to help show a compound is harmful, they don't feed the animals properly. There are a lot of tricks like that used in animal tests, so be careful what tests you read. Make sure you understand how the tests are performed. How they feed the animals while performing the tests can greatly impact the tests.

One problem with lab tests is that they can show a compound to be harmful that is actually a beneficial compound. Take vitamin C for example. Vitamin C is very acidic and can cause tissue damage if its concentrated enough. Tests employing concentrated solutions of Vitamin C on lab rats show it causes tissue damage and a bunch of other side effects. Does that mean Vitamin C is harmful? If you force feed a rat a ton of it everyday, the rat will get sick. Does that mean its harmful? No. It simply means the people performing tests are purposefully harming animals to get some sort of negative effects from a compound that is normally beneficial to humans. All compounds, even oxygen and water, are harmful in overdose. Some completely safe compounds become harmful when taken in concentrated form.

Such tests need to be looked at carefully. Results are often exaggerated, manipulated, etc.

I'm not saying these compounds are safe. I'm just saying they've never been proven to cause cancer in humans. Keep in mind that even apples and oranges contain many carcinogens. They are in everything we eat pretty much.

69Ron added 12 Minutes and 10 Seconds later...

Quote:
Originally Posted by phenythylamine View Post
afoaf is repeating these tests tonight, well let you all know how it goes, does anyone have a TEK to isolate anethol.


You can buy isolated methyl chavicol and convert it to anethol by heating it with potassium hydroxide in alcohol. You then wash with water to remove the alcohol and potassium hydroxide. It's very simple.

SWIM tried this German chamomile combo earlier today and is still feeling the effects from it.

He used 18 drops (386 mg) of basil oil (which is about 70% methyl chavicol) taken in a capsule with tea made from 1/4 cup of German chamomile flowers (ground after measuring the flowers).

The effects were VERY NICE and completely different from taking it without the German chamomile flowers.

Effects started at about 15 minutes in and consisted of a mescaline-like pleasant stimulation.

The peak was hard to ascertain, but seamed to happen at about 4 hours.

The effects included mescaline-like stimulation and mild euphoria, mild closed eye visuals, very mild open eye visuals, and an overall uplifting of the mood.

This is a combination SWIM will be trying again at a higher dose. It was definitely mildly psychedelic when taken with the German chamomile, but still on the weak side.

The same dose taken without the German chamomile mostly produced a mild withdrawn effect, some marijuana-like sedation, and extremely mild visual effects. The German chamomile really brought out the psychedelic effects of the basil oil, making it feel like a phenethylamine, and not a sedative.

Incidentally, SWIM has confirmed that methyl chavicol (assuming this is the active in basil oil) is completely cross tolerance with elemicin. The tolerance lasts a few days.

SWIM is going to try this at a higher dose some time in the future. It was quite nice, but still on the weak side.




69Ron added 145 Minutes and 4 Seconds later...

SWIM is still feeling the effects. It's been a good 6 hours and it's still going strong.

This has some elements of pure myristicin, and of elemicin/isolemicin, when they are used with 5 grams of German chamomile. This was a low dose of basil oil so it's hard to really categorize it, but it feels like it would potentiate the effects of these other psychedelics.

I'm envisioning that there exists a combination that produces a complete psychedelic state like that produced by LSD, including visuals, mental psychedelic effects, etc.

So far SWIM has obtained very good visuals from pure elemicin/isolemicin (when used with German chamomile), as well as a cheaper extract. These are full blown visuals like that of mescaline/LSD, but somewhat unique. At such a dose there is virtually no effect on the mind other that visual effects. (For those wondering, the dose SWIM uses for full visual effects is about 200 mg of pure elemicin/isoelemicin with 5 grams of German chamomile. Others may need a larger or smaller dose.)

With myristicin, effects are more like MDMA, and SWIM is not that interested in it. But a small dose does go well with elemicin, adding some mental psychedelic effects, but at higher doses, SWIM doesn't like it much. Methyl chavicol seems nicer than myristicin, so far.

SWIM has also played with methyl eugenol. He's got a light Psilocybe azurescens like body feel from it, and a feel that its about to be psychedelic, but so far no psychedelic effects have been felt from it. It does however potentiate the effects of elemicin, making it a little more like DMT, and it seems to prolong the effects. Again all of these tests are using 5 grams German chamomile in addition to the oils.

Eugenol also potentiates the effects of elemicin, but its easy to use a little too much. It's extremely potent with just a few drops being good and a few more drops ruining the trip. This is only good at 4 drops or less. Eugenol does add a slight LSD-rough edge to the elemicin trip. I think this might be useful at a few drops in a super mix of these psychedelic oils, but the dose has to be very low.

My idea is to have SWIM try a mix of primarily elemicin/isoelemicin (for visuals), a good portion of methyl chavicol (for the body feel), a good portion of methyl eugenol (for a slight DMT-like twist), and a tiny bit of eugenol and myristicin (for LSD-like mental effects). Of course all taken in capsules with the tea of 5 grams of German chamomile. There's no point testing without the German chamomile. Without it, sometimes these oils do nothing at all. I think that's why a lot of people don't know these things work. Taking them without German chamomile is almost like taking DMT orally without an MAOI. At this point I consider German chamomile a requirement when taking these oils if you want any decent effects from them.

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Great experience report, and helpfull information regarding isolating actives from oil, +6

Last edited by 69Ron; 15-01-2011 at 11:11. Reason: Automerged Doublepost
  #6  
Old 15-01-2011, 21:20
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Re: an exploration of methyl chavicol

Sleep paralysis while trippin (an experience with high dose basil oil and woodrose.)

Dose: 40 drops sweet basil oil + german chamomile tea, as well as 10 drops german chamomile oil added
Ingestion time: 12:00

1:00: afoaf is feeling mild stimulation building, similar to small dose of mescaline.

2:00: mild CEVs similar to low dose of mescaline, mostly closed eye patterning, not very much definition though.

3:00 feeling stronger effects now, subtle euphoria as well as mild tracers, vision seems to be lagging a little.

3:15 seems to be peaking, definite CEVs and OEVs although very mild, walls seem to be breathing a little bit, colors are enhanced, notable music appreciation.

3:30 begin chewing 5 hawaiian baby woodrose seeds seeing as how elemi oil potentiates them (at least in my experience, thanks 69ron for the idea lol,) seeds are chewed for about 30 minutes and sit under tounge for another 30 minutes.

4:30 seed mush is spit out, dont want to swallow these mother fuckers as nausea is already apparent (something that really doesent happen using HBWR alone even in much larger doses.)

5:00 something is really really off, its like my eyes cant possibly keep up with my vision, music sounds very very very loud even though master fader on afoafs console is almost all the way down. afoaf decides to kill the music, turn fader all the way down. WTF music is still playing for about 10 seconds after music should have stopped, either afoafs experiencing technical difficulties or he is trippin balls lol.

6:00 still going strong, amazing euphoria, feels like a good dose of MDMA now with mescaline like visuals, waves of color, fractal patterns, ect. afoafs HBWR trips are usually not very visual, however it seems the sweet basil oil potentiated it greatly.

stopped keeping track of time, strange afoaf feels kinda sleepy now, even though he felt stimulated earlier, must be the woodrose.

effects begin to subside maybe about a few hours later, afoaf decides to call it a night and go to bed early, very very vivid dreams. being in a dark room brought the trip back substancially as well.

now this is when something really really weird happened. afoaf was falling into REM sleep, when his phone alarm went off, fuck he forgot to turn it off, but when he tried to get up to turn it off he couldent move, his chest tightened and he saw the most amazing bright light he has ever seen, it was as if "god" was reaching down trying to pull afoaf up towards heaven, he even felt what he described as the hand of god on his shoulders lifting him out of bed, keep in mind afoaf does not believe in god, after being "pulled out of bed by god," afoaf woke up in his bed with a jolt and a scream, he was drenched in sweat. afoaf having had experience with sleep paralysis before quickly knew what happened, so after a few moments of alarm he settled back down and drifted off into a very lucid dream of flying over a city, much like the movie enter the void.

anyways just wanted to share this report with you guys on a little known combination, this might actually deserve a thread of its own, if you guys feel thats the case please move it.


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Great info and trip report.
  #7  
Old 15-01-2011, 23:21
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

What a cool and inspiring trip report Phenythylamine!

It seems like basil oil (when taken with German chamomile) is a decent experience for more than just SWIM. It's good to see someone else performing these tests and getting similar results.

It amazes me that something as common as basil oil is psychedelic when combined with German chamomile. SWIM's take is that the experience is as good as a low dose of mescaline. Very positive. There were no side effects like you can get from some elemi oil. SWIM's oil is about 70% methyl chavicol. You can legally buy pure methyl chavicol in most parts of the world. SWIM will try pure methyl chavicol eventually so he can be sure just what exactly is producing these beautiful effects.

Note to others reading this thread. There are two kinds of basil oil generally available. One is high in linalool and the other high in methyl chavicol. I believe you need the variety high in methyl chavicol. It usually says what kind it is on the bottle. Don't bother trying it without German chamomile. If you do, chances are you'll get sedative effects and not psychedelic effects. It's not very interesting without the German chamomile.

Another way of looking at this is that CYP1A2 enzymes maybe make these oils sedating and non-psychedelic. CYP1A2 enzymes are normally the primary enzymes to attack these oils. But when CYP1A2 is inhibited these oil are instead attacked by something else in the body, but instead of inactivating them, this other process causes them to be psychedelic and no longer substrates of CYP1A2. This is just my theory.

The reason I think this is because after the mescaline-like effects kick in for these oils, you can cause yourself to be high in CYP1A2 by drinking a lot of coffee, or smoking, eating burnt meat, etc., and that no longer causes the basil oil to be sedating and uninteresting. It's as if once the effects start when CYP1A2 is inhibited, afterwards CYP1A2 can no longer metabolize these oils when it's levels go back to normal. It's like a change to these oils is made, rendering CYP1A2 ineffective against them.

It's like this:

elemicin + CYP1A2 = sedative
myristicin + CYP1A2 = sedative
methyl chavicol + CYP1A2 = sedative

But inhibit the CYP1A2 and it's like this:

elemicin + other enzyme = psychedelic
myristicin + other enzyme = psychedelic
methyl chavicol + other enzyme = psychedelic

Normally what happens when you inhibit one enzyme is that another enzyme takes over the job of metabolizing the compound, when possible.

From what I understand CYP1A2 is primarily responsible for the potential carcinogenicity of things like safrole (taken in massive doses for weeks at a time), by altering it into a possible carcinogen. With CYP1A2 inhibited, things like safrole should be much safer. If safrole is taken with a CYP1A2 inhibitor will you get a decent experience from it like that produced from these other oils? This can be tried with sassafras. You can brew a strong cup of sassafras and take it with 5 grams of German chamomile. I'll bet it's effects will shift from being a boring mildly sedating tea to being almost just like MDMA. SWIM hasn't tried this but is willing to bet that it works.

I'll bet acorus calamus is also better when taken with 5 grams of German chamomile. This is something SWIM is a little nervous about trying after he once overdosed on acorus calamus a while back (it caused horrible non-stop nausea and vomiting that lasted about 8 hours straight!).

Last edited by 69Ron; 15-01-2011 at 23:27.
  #8  
Old 16-01-2011, 03:07
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Re: an exploration of methyl chavicol

yeah afoaf is getting real into exploring essential oils after reading a few of your posts, he finds the synergy with HBWR to be amazing. Didnt expect the sleep paralysis though, shouldent have even added the woodrose concidering afoaf was meaning to test this alone, desire to strengthen effects got the best of afoaf.
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Old 22-01-2011, 04:46
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

The combination of German chamomile and methyl chavicol is a GREAT ANTIDEPRESSANT!

I think a good test is to use methyl chavical, elemicin/isoelemicin, and German chamomile simultaneously. I’ll bet the methyl chavical and elemicin/isoelemicin will greatly boost each other’s effects. I imagine using methyl chavical as a booster will work in much the same way as HBWR works to boost elemicin’s effects.

Note that I’ve not heard of large doses of methyl chavical being used. There may be undesirable side effects as the doses increase. So far SWIM has not felt any. But be careful. This is a pretty uncharted area of herbal science.
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Old 27-01-2011, 09:35
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Re: an exploration of methyl chavicol

Cigarette smoking causes a great increase in CYP1A2. This theoretically leads to the creation of cancer causing substances in the body. For health reasons its generally considered best to avoid things that increase CYP1A2 enzymes.

In women with breast cancer, studies have shown these women tend to be higher in CYP1A2. Smokers with lung cancer are also higher in CYP1A2 than the rest of us.

One study concluded that
Quote:
increased CYP1A2 function may be associated with increased risk for breast cancer
If you smoke regularly (even marijuana does this) you will have a high level of CYP1A2 and you are at a much greater risk for developing cancer. That’s what a lot of studies seem to suggest anyway. Burnt particles in the smoke cause a rise in CYP1A2 enzymes. It has nothing to do with tobacco or marijuana. Smoking anything pretty much does this.

German chamomile reduces CYP1A2 levels dramatically. When taking safrole or sassafras, German chamomile should greatly reduce the potential carcinogenicity of safrole. CYP1A2 is known to metabolize methyl chavicol into a potential weak carcinogen. In one study CYP1A2 inhibition completely blocked the potential carcinogenicity of methyl chavicol. The study focused on basil oil, and determined that the mild CYP1A2 inhibitors present in basil oil were enough to prevent methyl chavicol from metabolizing into a potential weak carcinogen.

An excerpt from another study,
Quote:
This is exemplified by aristolochic acids (AAs) in Aristolochia spp, which undergo reduction of the nitro group by hepatic CYP1A1/2 or peroxidases in extrahepatic tissues to generate highly reactive cyclic nitrenium ions. The latter can react with macromolecules (DNA and protein), resulting in activation of H-ras oncogene and gene mutation in renal cells and finally carcinogenesis of the kidneys. Some naturally occurring flavonoids (e.g. quercetin) and alkenylbenzenes (e.g. safrole, methyleugenol and estragole) can undergo metabolic activation by sequential 1-hydroxylation and sulfation, resulting in reactive intermediates capable of forming DNA adducts and finally genotoxicity.
CYP1A2 is not good to have an abundance of when taking alkenylbenzenes like safrole, methyl eugenol, methyl chavicol (estragole), elemicin, or myristicin. Pretty much all of the psychedelic oils should not be taken without a CYP1A2 inhibitor.

In reality, these oils have a low risk of carcinogenicity, so there’s not much to worry about, but since they are more psychedelic when CYP1A2 is inhibited and their potential carcinogenicity should be greatly reduced, why bother taking them without German chamomile?


AFOAF has tried taking sassafras with German chamomile and guess what, the effects are totally different as was theorized. Instead of a mild sedative effect he normally gets, he experienced pretty good stimulation, an increase in sensitivity to touch, his body felt warmer, etc. It was a totally different experience with the German chamomile. My guess is that with CYP1A2 inhibited, the body cannot convert safrole into a sedative, and is instead converting it to a stimulant. There were some possible psychedelic effects, but they were too weak to be certain they were not placebo. The stimulant effects were absolutely NOT placebo. It was pretty strong. He felt strong tingling sensations in his body as well. All of the effects felt were effects that can be attributed to a dose of MDMA, except there was no increase in euphoria or empathy felt, which might just mean the dose was too small.

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Last edited by 69Ron; 28-01-2011 at 19:09.
  #11  
Old 12-02-2011, 21:19
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Re: an exploration of methyl chavicol

A while ago, the goodly knight Sir Marhaus, the King’s son of Ireland was forced to imbibe basil essential oil (ocimum basilicum) by the evil sorceress Morgan le Fay. He told me that the sorceress first prepared a brew of 5g of german chamomile tea. He consumed the tea and shortly after that, 1ml of basil essential oil in a drained fish oil capsule. And nothing much happened. He said he felt some mild stimulation and maybe—maybe—the walls were somewhat breathing but that could have been his imagination.
Could it be that Morgan le Fay used the wrong type of oil (I see sweet basil oil here, Sir Marhaus makes no mention of the oil being sweet basil…) or used it in not enough quantity?
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Old 13-02-2011, 00:17
phenythylamine phenythylamine is offline
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Re: an exploration of methyl chavicol

both elemi and sweet basil oil have been pretty mild at the doses afoaf attempted, but both seem to be potentiated by the addition of LSA.
also some people just dont get much off of these oils, or maybe a higher dosage needs to be consumed, or more likely the oil used was low in the actives.
  #13  
Old 13-02-2011, 03:58
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

Contact, the oil dose is probably too small for that individual, or it might be low in methyl chavicol. Some basil oil is almost void of methyl chavicol and simply won't work. Make sure the basil oil is the kind high in methyl chavicol. It should say on the bottle or in the add that it’s the methyl chavicol chemotype. Not all sweet basil is high in methyl chavicol.

Some people are notoriously insensitive to these oils, requiring massive amounts for effects. That individual might be such a person.

Also, methyl chavicol is made inactive by both CYP1A2 and CYP2A6. If a person is high in either enzyme they will NOT TRIP AT ALL. The same is apparently true for elemicin. German chamomile only inhibits CYP1A2. However, cinnamon oil inhibits CYP2A6.

To be sure of proper enzyme inhibition it’s advised to use both German chamomile and cinnamon oil. I know of one person who doesn’t get effects if German chamomile is used but does get effects if cinnamon oil is used. Every one is a little different and even on different days one’s enzyme levels change. The key is to inhibit both enzymes. This also apparently applies to elemicin as well.

Last edited by 69Ron; 13-02-2011 at 04:11.
  #14  
Old 25-02-2011, 01:59
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

About 1 hour ago, AFOAF took the following all in one size 000 capsule:

12 drops (285 mg) pure methyl chavicol
3 drops (59 mg) German chamomile essential oil
6 drops (169 mg) cinnamon bark essential oil
22 drops (709) vegetable oil (as a filler)

Before taking it, the capsule was shaken vigorously. It was taken with 1/2 cup of water on an empty stomach.

At this point, about 1 hour later, the effects are obvious, but they are a MIX of sedative effects and psychedelic effects.

Apparently it's NOT a good idea to mix everything and take it all at once in a capsule. The CYP1A2 and CYP2A6 inhibitors didn't have enough time to do their job this time and so instead of a good decent trip, he's got a mix of sedation and psychedelia, which is not so good.

Does anyone know the proper amount of time for the German chamomile oil and cinnamon bark oil to inhibit CYP1A2 and CYP2A6?
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Old 25-02-2011, 06:36
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Re: an exploration of methyl chavicol

Quote:
Originally Posted by 69Ron View Post
Does anyone know the proper amount of time for the German chamomile oil and cinnamon bark oil to inhibit CYP1A2 and CYP2A6?
The attached study found by SWIM may indirectly help SWIY with finding the right timing and method of consumption of Cinnamon oil.

Figure 1 on page 5 shows the peak times when the compound Coumarin is present in the subjects plasma. One would think it could be a good assumption to correctly time when CYP2A6 is fully inhibited...

Peak presence of Coumarin range anywhere from 30-60 minutes depending on vehicle of consumption

Hope this helps for now, SWIM will look for CYP1A2 later if SWIM can.

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File Type: pdf cinnomon_effects_timed.pdf (198.4 KB, 9 views)
  #16  
Old 25-02-2011, 09:31
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

Everyone gets cassia confused with cinnamon. A lot of studies on "cinnamon" are actually studies done using cassia unfortunately. As is the case in that document you attached.

ElusiveMind, that document is helpful for people using cassia bark oil for its coumarin content, but doesn't apply much to true cinnamon bark oil.

By your action of posting that document, I'm prompted to point out the differences between cassia and true cinnamon, which is a good thing for our readers out there to be aware of.

Coumarin is not in true cinnamon bark oil except as a trace element in some varieties, and not present in the oil AFOAF is using.

It's cinnamaldehyde and not coumarin in cinnamon bark oil that's responsible for it's potent CYP2A6 inhibition.

Coumarin is found in cassia bark oil in substantial quantities, on average about 63 times more than is found in true cinnamon. Cassia is commonly known as Chinese cinnamon in the aromatherapy world. AFOAF doesn't have that kind of oil and is not interested in it because of the high coumarin content.

In the aromatherapy world, the distinction between cinnamon and cassia is made very strongly. They have somewhat different therapeutic actions because cassia contains quite a bit of coumarin while true cinnamon contains either no coumarin or only traces of it. While they taste similar and can pretty much be used as spices interchangeably, that doesn't exactly apply when using them for therapeutic purposes.

Cinnamon bark oil contains mostly cinnamaldehyde. That's pretty much the only active present in it in normal doses. But cassia bark oil contains enough coumarin to get effects from it at normal doses.

With the doses AFOAF is using (3-10 drops) there is no effect at all from the coumarin. At up to a maximum of 0.45% coumarin, true cinnamon only contains at most about 4.5 mg per ml, some contains NO coumarin (the kind AFOAF is using doesn't contain it), while cassia contains up to 50 mg per ml. 10 drops of oil weighs 266 mg, at up to 0.45% coumarin, a 10 drop dose contains up to 1.197 mg of coumarin. That's not enough to do anything at all.

5.6 mg per day of coumarin is considered SAFE by the European Food Safety Authority. 46 drops of true cinnamon oil contains up to 5.6 mg of coumarin (but some varieties contain no coumarin). Cassia contains a lot more. 4 drops of cassia oil contains up to 5.6 mg of coumarin.

So if you're using cassia oil and you want to stay within the safety guidelines defined by the European Food Safety Authority, then 4 drops per day is the highest dose you should use. For true cinnamon, 46 drops per day, unless its the kind free of coumarin (like what AFOAF is using), which in that case this coumarin information doesn't apply.


Considering the peak concentration time of coumarin is 30-60 minutes, even though it's not in AFOAF's oil, and not the compound of interest, it does at least give some rough estimate as to the possible peak concentration of cinnamaldehyde after ingestion. It's probably something similar. The German chamomile's oil azulene probably has a similar peak time. I wonder if inhibition of the CYP1A2 and CYP2A6 enzymes follow this peak time or not?


It's been AFOAF's observation in his own body that using German chamomile tea to swallow a capsule of methyl chavicol always works. However, taking German chamomile oil in the capsule with methyl chavicol is iffy. I think this is because the tea is more rapidly absorbed, while the capsule sits around for a while in the stomach before opening, so the inhibitors in the tea are already active before most of the methyl chavicol comes out of the capsule. But if the inhibitor oil is in the capsule with the methyl chavicol then they come out at the same time, so it's less effective sometimes.

This probably also applies to elemicin. AFOAF is going to have to test this timing thing out more. Taking the inhibitor oils in a capsule with the psychedelic oil is not a good idea. AFAOF is going to start tying a 30 minute pre-dose using the inhibitor oils. Hopefully that makes a difference.

Last edited by 69Ron; 25-02-2011 at 09:38.
  #17  
Old 25-02-2011, 12:48
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Re: an exploration of methyl chavicol

Hi all!

A frog ordered from a web shop thoses oils in order to experiment with different combinations.

She got confused when it was about chosing the cinnamon oil.

Here is what's written on the web site: (yes the frog can read french)

Composition Cinnamomum cassia :
Principaux constituants biochimiques -

Chromatographie phase gaz du lot(batch) LE129 :

Aldéhydes : (E)-cinnamaldéhyde (78.84%), (Z)-cinnamaldéhyde (0.36%)
Sesquiterpènes : béta-caryophyllène (0.37%), alpha-copaène (0.28%)
Alcools : alcool-(E)-cinnamyle (0.18%)
Esters : acétate de cinnamyle (3.19%), benzoate de benzyle (0.07%)

The frog also asked them the amount of courmarin and styren

- coumarine non détéctée

- styrène 0.13%

Chromatographie phase gaz du lot(batch) LE318 :

Aldéhydes : (E)-cinnamaldéhyde (85.51%), (Z)-cinnamaldéhyde (0.19%)
Sesquiterpènes : alpha-copaène (0.19%)
Alcools : alcool-(E)-cinnamyle (0.043%)
Esters : acétate de cinnamyle (0.89%), benzoate de benzyle (0.06%)
- coumarine 0.861%

- styrène 0.104%

Composition Cinnamomum verum (bark)
- Chromatographie phase gaz du lot LE054 :

Monoterpènes : béta-phellandrène (2.36%), para-cymène (1.46%), alpha-phellandrène (1.31%), limonène (0.60%), alpha-terpinène (0.56%), alpha-pinène (0.47%), béta-pinène (0.23%), camphène (0.20%), terpinolène (0.18%), myrcène (0.12%)
Monoterpénols : linalol (3.39%), alpha-terpinéol (0.52%), terpinène-4-ol (0.25%), alcool (E) cinnamyle (0.11%)
Aldéhydes : (E)-cinnamaldéhyde (68.69%), (Z)-cinnamaldéhyde (0.42%)
Esters terpéniques : acétate de cinnamyle (4.35%), benzoate de benzyle (0.82%)
Phénols : eugénol (2.62%)
Sesquiterpènes : béta-caryophyllène (6.33%), alpha-humulène (1.08%), alpha-copaène (0.71%)
Oxydes : 1.8 cinéol (0.12%)

From what she understood, the first batch of cassia would be the best of the three oils?

She's planning to ingest several drops (following 69ron's previous posts)
of cassia oil with Matricaria chamomilla's oil .

Wait 20 min and then few drops of Ocimum basilicum with this

Monoterpènes : (E)-béta-ocimène (1.29%), béta-pinène (0.40%), limonène (0.29%), myrcène (0.28%), alpha-pinène (0.24%), sabinène (0.19%), para-cyménène (0.13%)
Monoterpénols : linalol (0.86%), terpinène-4-ol (0.32%)
Phénols méthyl-éthers : méthyl-chavicol (85.32%), méthyl-eugénol (0.43%)
Oxydes : 1,8-cinéole (3.31%)
Sesquiterpènes : (E)-alpha-bergamotène (2.46%), gamma-cadinène (0.45%), béta-élémène (0.29%), béta-caryophyllène (0.17%)
Sesquiterpénols : épi-alpha-cadinol (0.58%)
Cétones : camphre (0.43%)
  #18  
Old 26-02-2011, 00:27
ElusiveMind ElusiveMind is offline
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Re: an exploration of methyl chavicol

Thanks 69Ron for the long explanation on Cassia vs True Cinnamon. SWIM did not know there was that much of a difference in Cassia cinnamon. The difference between them can be confusing as they supposedly taste very similar too. Heck, the store that SWIM usually goes to for essential oils even told SWIM the cinnamon bark oil they had was "true cinnamon" (while giving SWIM a weird look ). Since they were only selling it as "cinnamon bark essential oil", SWIM asked them to look up the species of cinnamon they were selling and low and behold, it was Cassia cinnamon... not True cinnamon

Interesting yafohi! has posted with percentages of cinnamaldehyde.... Cassia species showing that it does consist of a higher concentration of cinnamaldehyde than SWIM thought.... ..... so... does Cassia species really contain that high of a percentage or does the (E) and (Z) in front of the cinnamaldehyde mean it is different than regular cinnamaldehyde??

confused.....
ElusiveMind
  #19  
Old 26-02-2011, 02:25
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

Cassia essential oil is cheaper, so beware: some places sell cassia as if its true cinnamon, even putting the wrong botanical name on it on purpose to make extra profit.

Even some big time oil retailers get ripped off once in a while when they purchase true cinnamon essential oil in bulk and are given cassia oil instead. This is a known problem in the aromatherapy world. It’s sad. But reality.

69Ron added 43 Minutes and 40 Seconds later...

Quote:
Originally Posted by ElusiveMind View Post
does Cassia species really contain that high of a percentage or does the (E) and (Z) in front of the cinnamaldehyde mean it is different than regular cinnamaldehyde??

confused.....
Yes, it is confusing.

The (E)-cinnamaldehyde is the typical form found in these oils. That’s the potent CYP2A6 and CYP2E1 inhibitor.

Some companies post GCMS data, but keep in mind that in reality that only applies to one batch. Every single batch will differ. True cinnamon normally contains little or no coumarin, while cassia usually contains a lot. That’s one major difference between the two. But not all cassia contains a lot of coumarin. Some is very similar to true cinnamon and can fool even the pros. True cinnamon usually contains more (E)-cinnamaldehyde than cassia, but not always.

Coumarin is really the main thing that separates true cinnamon from cassia. Look here:

Quote:
What true cinnamon and cassia do not have in common is their coumarin content. Coumarins are naturally occurring plant components that can have strong anticoagulant properties. Because our blood needs to maintain its ability to coagulate in times of injury, excessive intake of coumarins over a prolonged period of time can pose health risks. While the level of naturally occurring coumarins in Ceylon cinnamon appears to be very small and lower than the amount that could cause health risks, the level of naturally occurring coumarins in the cassia cinnamons appears to be higher and may pose a risk to some individuals if consumed in substantial amounts on a regular basis. For this reason, organizations like the Federal Institute for Risk Assessment in Berlin, Germany have recommended that large amounts of the cassia cinnamons be avoided.
I personally think the risk is way overblown. These health organizations find health risks in almost everything. But I feel people should be aware of this. If you are worried about this, choose true cinnamon over cassia. Or possibly try to find another good CYP2A6 inhibitor that doesn’t also inhibit CYP2D6 or CYP3A4. I don’t know of one that is as selective as cinnamon oil. If anyone does, please post it!

69Ron added 22 Minutes and 18 Seconds later...

Quote:
Originally Posted by yafohi! View Post
From what she understood, the first batch of cassia would be the best of the three oils?

She's planning to ingest several drops (following 69ron's previous posts)
of cassia oil with Matricaria chamomilla's oil .

Wait 20 min and then few drops of Ocimum basilicum with this
That first oil is a very good cassia oil. That should work well.

The doses I outlined work for AFOAF. He knows the amount of inhibitor oils that work for his body. Each person is different and will need a different amount of inhibitor oils. If one gets a mild sedative effect and that’s all, the inhibitors were not effective. Next time try doubling the inhibitor dose. It’s safer to up the German chamomile dose than the cinnamon dose, because German chamomile is extremely safe. One can easily take up to 18 drops without any issues. That’s the amount of oil in 30 grams of German chamomile flowers, which is a safe dose.

I don’t know the maximum safe dose of cinnamon oil, but there is a known case of a child taking 60 ml of cinnamon oil. He experienced "vomiting, diarrhea, and loss of consciousness", but the child recovered. 60 ml is about 2250 drops. That's 375 times the 6 drop dose AFOAF is usually using and he’s an adult.

The inhibitor dose AFOAF uses for methyl chavicol also works well for elemicin. So once one establishes their inhbitor dose for methyl chavicol it should also apply to elemicin, safrole, and most of the other similar oils.

Last edited by 69Ron; 26-02-2011 at 02:25. Reason: Automerged Doublepost
  #20  
Old 21-04-2011, 18:10
Dorge Dorge is offline
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Re: an exploration of methyl chavicol

This is all very interesting stuff. Afoaf tried the Elemi oil his own and it had slight effects for him and his compariates...
What's interesting is this new development with the German chamomile.
Does it have to be German chamomile or will any ol chamomile due?

I distill essential oils. And it's rather easy for essential oils to be distilled into alcohol by macerating the herbs first then distilling the menstrum. This is how absinthe is traditionally made, it is also how anisettes like Raki and Ozo are made.
It makes me wonder...
Could chamomile be added to traditional absinthe recipes to increase the effects of the essential oils in absinthe? Could an absinthe like drink be made by adding the basil oil and the chamomile?
I know that Elemi oil is far too strong tasting at the proper dose range to be added to a beverage. But could an extracted elmicin or the methyl chavitol be added to a chamomile infused liquor?

Absinthe is basically an alcoholic beverage infused with essential oils and then slightly flavoured with a slight infusion of herbs for taste and color.
Typical ingredients for absinthe
Worm wood... Source of Thujone
Lemon balm
Mint
Hyssop
Fennel
Licorice
Anise
Star anise
Calmus root

All high in essential oils.

Are the oils in anise possibly altered with the addition of chamomile? Would Thujone be altered by the addition of chamomile in it's effects?

The possibility of creating new essential oil infused (through distillation) beverages like absinthe and raki and Ozo is a really exciting notion.
Chamomile and sweet basil can be dry or fresh and placed in 190 grain or grape ethanol. This can be soaked in a cool dark place for weeks then strained and a 1:1 ratio of water to menstrum can be combined. The menstrum can then be distilled and one will have a lovely clear slightly blueish hued beverage.
Yes that's right blueish! Chamomile oil when distilled properly can appear blue. Neat huh!
This alcohol can then be further diluted in a glass with Ice water producing the ever popular louche effect. The oil particles will micro particle/separate and the beverage will turn a lovely milky color.
A foaf distills a purple raki or Turkish anisset made with black mission figs and anise that's to die for.
Lots of experiments here. How exciting!

Dorge added 25 Minutes and 48 Seconds later...

I did a little home work. Eygeptian chamomile is the same species as well as going by other names.

Matricaria recutita, Hungarian chamomile or wild chamomile, Camomilla, Camomille Allemande, Chamomile, Chamomilla recutita, Echte Kamille, Feldkamille, Fleur de Camomile, Kamillen, Kleine Kamille, Manzanilla, Matricaire, Matricaria recutita, Matricariae Flos, Pin Heads, Sweet False Chamomile, True Chamomile.

The roman variety also known as the English variety is Anthemis nobilis

Last edited by Dorge; 21-04-2011 at 18:10. Reason: Automerged Doublepost
  #21  
Old 25-04-2011, 05:34
psilocybechild psilocybechild is offline
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Re: an exploration of methyl chavicol

German chamomile is a potent CYP1A2 inhibitor. It'll only have an effect on the thujone or any of the other essential oils if their constituents are broken down by the CYP1A2 enzyme.
  #22  
Old 19-05-2011, 04:45
69Ron 69Ron is offline
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Re: an exploration of methyl chavicol

One could make an absinthe like drink using sweet basil oil, German chamomile oil (chamomile blue), and cinnamon bark oil. In order to make it pleasant tasting (if that’s even possible), one is going to need to dilute it quite a bit.

Dorge, I think absinthe was one of the original oilahuasca’s. There were several kinds made, and some were absolutely psychedelic if you read the history on it. I have often read that one needed to drink it a few times before the psychedelic effects kicked in. One serving, no matter the size would just make you a little drunk. But taking it a few times in a row produced psychedelic effects. This indicates that enzymes are inhibited with the first few glasses of absinthe, and then if one continued drinking it, the psychedelic oils would be properly metabolized.

The problem is that a lot of the good recipes are lost, and often times the oils used were not actually the oils they were sold as. Imported oils were sometimes similar cheaper oils or oils adulterated with other oils. This issue of essential oil adulteration continues even today.
  #23  
Old 27-05-2011, 07:06
Shanty Shanty is offline
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Re: an exploration of methyl chavicol

Swim looked all over this thread. Where is methyl Eugenol from?

Swim has experienced mild DMT like effects from Calea zacatechichi while in a waking state. Perhaps this is worth some side investigation.
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Old 27-05-2011, 16:29
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Re: an exploration of methyl chavicol

Quote:
Originally Posted by Shanty Finn View Post
Swim looked all over this thread. Where is methyl Eugenol from?

Swim has experienced mild DMT like effects from Calea zacatechichi while in a waking state. Perhaps this is worth some side investigation.
Methyl Eugenol is found in Mexican Allspice (pimenta officinalis), along with some other plants in that genus and possibly outside it too. In fact some of the pimenta essential oils contain quite a mixture of chemicals.

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Good, quick answer. To the point.
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Old 15-06-2011, 07:23
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Re: an exploration of methyl chavicol

afoaf has some estragole but no scale to measure out a dose between 200 and 400mg as is recommended. she found that its solubility in water at room temperature is around 178mg per liter. would it be reasonably safe then for her to eyeball the dose into say 1.5 liters of water and mix it up until solids begin to settle, then consume the water leaving behind whatever concentration of estragole has settled at the bottom of the container?

Apparently it is also soluble in ethanol and dmso. the ratio is unknown to her though...

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