Is safrole psychedelic?

[Ginkgo]

Thanks a lot for that bioassay, The Traveler! What supplier did your oil originate from? I'm wondering if the sedative effects are caused by elemicin itself or by some other compound(s) in the oil. My guess is that elemicin is a stimulant, whereas one or more other compounds are sedatives.

According to FV, one sample of elemi oil contained:
54.10% Limonene
15.10% alpha-Phellandrene
15.00% Elemol
3.50% Elemicin
2.50% 1,8-Cineole
2.40% Myrcene
1.50% para-Cymene
0.80% beta-Phellandrene
0.60% Terpinolene
0.40% gamma-Terpinene
0.40% alpha-Pinene
0.30% Methyl eugenol
0.20% Carvone
0.30% trans-p-Mentha-1(7),5-dien-2-ol
0.10% Carvotanacetone

I'm guessing one or more of these are sedatives. Elemol strike me as a possible sedative. Perhaps we should work out a tek to obtain more or less pure elemicin? Alpha-Phellandrene is also unwanted, in higher doses it may lead to vomiting and diarrhea.

By the way, FV's elemi oil is considerably cheaper now! Now it is really a great price even compared to the cheapest internet sources.

 

[The Traveler]

Going back to this, at about 0.55 ml (about 20 drops)

The 20 drops I took were a total of about 1 ml, it completely filled the big half of the capsule (the part that is not the cap). Afaik, a OOO capsule is 1.37ml, or am I wrong here?


Kind regards,

The Traveler

 

[69ron]

Today I tried the Elemi oil as well.

After I woke up from a 10 hours sleep, I prepared my Elemi oil by dripping 20 drops into a OOO capsule. I took the cap with a glass of water on an empty stomach. The gelcap popped rather fast in my belly because within a few minutes I burped my first fragrance.

Right after that I took a glass of liquidly porridge (Brinta for those who want to know) followed with a cup of coffee to activate my digestive tract.

Within 10 minutes(!) of swallowing the gelcap I could feel the effects coming on. I could feel a tension build up together with a slight euphoria, pretty much like I have with the onset of LSD. Then, probably because I took 20 drops, a sedation came on, and like 69ron stated it made me feel a little withdrawn. I didn't like to talk to my GF anymore but just wanted to stare in front of me doing nothing. Reading from the screen of the laptop became more difficult because I needed more concentration to read what was on the screen. When I looked at my GF I could see slight visuals surrounding her. With my eyes closed there were visuals too, of the wavy/flickering kind.

Then the sedative effect came more and more into play, pushing away any of the euphoria and energetic tension I had, it also pushed away any visuals. This lasted for about 4 hours with the sedative peak at the 1 hour mark then slowly subsiding.


So to resume: the elemi oil worked but when the sedative effect fully kicked in it was the only thing left. The sedative effect wasn't unpleasant but I couldn't see any use for it either.

Next time I will take just 10 drops and see how that will effect me, if the sedative effects stay away I could see this as a nice compliment of my entheogen use.


Kind regards,

The Traveler

It’s likely at 5-10 drops you won’t notice the sedative effect. SWIM’s oil is not sedating at 10 drops or less. At 20 drops the sedative effect is pretty obvious and SWIM doesn’t like it much.

I would love to know how to remove the sedative component or increase the effectiveness of the elemicin so that a lower dose can be used. At higher doses the sedative component messes it up.

This sedative component could help explain why Elemi oil use as a psychedelic is not widespread.

 

[69ron]

Going back to this, at about 0.55 ml (about 20 drops)

The 20 drops I took were a total of about 1 ml, it completely filled the big half of the capsule (the part that is not the cap). Afaik, a OOO capsule is 1.37ml, or am I wrong here?

I don’t know about the OOO capsules, but the drop size depends on the dropper used and the thickness of that particular batch of oil, and the room temperature. It’s an inaccurate way to count dosage. SWIM is using a pipette now and measuring dosage by ml, and is no longer counting drops. His pipette gives a much higher drop count than his euro-dropper does, for the same quantity of oil. So drop count is a poor way to measure dosage.

 

[Dorge]

Then the sedative effect came more and more into play, pushing away any of the euphoria and energetic tension I had, it also pushed away any visuals. This lasted for about 4 hours with the sedative peak at the 1 hour mark then slowly subsiding.


So to resume: the elemi oil worked but when the sedative effect fully kicked in it was the only thing left. The sedative effect wasn't unpleasant but I couldn't see any use for it either.

Next time I will take just 10 drops and see how that will effect me, if the sedative effects stay away I could see this as a nice compliment of my entheogen use.


Kind regards,

The Traveler

SWIM also got the sedative effects but figured he was just tired... that would explain that.

 

[imPsimon]

Elemicin is not an alkaloid so taking harmaline with it is not really going to boost the effects much. It will alter the effects, making it sort of ayahuasca like, but it doesn’t really boost the effects much.

Isn't TMA an alkaloid? If it is indeed converted to tma shouldn't there be
harmaline potentiation?


I tried 30 drops in a gel cap saturday together with some 5 d. stramonium seeds.
No visuals were present but there was some definite effects.
Problem focusing which I have observed on earlier experiments were present.
I became giggly and started laughing for no obvious reason.
Things looked a little different with textures popping out more then usual.
Some sedation were also present.

In a previous experiment I took a book to the park
hoping to do some reading in the sun but as soon as the
capsule kicked in all I could do was listen to music and watch the flowers and the
other people in the park.

I'm going to wait for some elemioil from FV before I do my next experiment.

 

[69ron]

I'm wondering if the sedative effects are caused by elemicin itself or by some other compound(s) in the oil. My guess is that elemicin is a stimulant, whereas one or more other compounds are sedatives.
...
Elemol strike me as a possible sedative. Perhaps we should work out a tek to obtain more or less pure elemicin? Alpha-Phellandrene is also unwanted, in higher doses it may lead to vomiting and diarrhea.

I would tend to believe that most compounds are not going to be very active unless at least 5 mg or more are ingested. So, I’d look at:

* limonene - sedative
* alpha-phellandrene - unknown
* elemol - unknown
* elemicin - stimulant
* 1,8-cineole (eucalyptol) - sedative
* myrcene - sedative

Each test I’ve seen shows quite a big variance in components. But usually elemol, d-limonene, and sometimes alpha-phellandrene are the major components. Sometimes the three main components are d-limonene, elemicin, and elemol. Elemol is usually listed as a main component, with d-limonene nearly always being number 1.

Every reference I’ve seen to elemicin says it’s a stimulant, so I think we can rule that one out.

Elemol is an alcohol. According to several tests I’ve seen there’s often quite a bit of it present. I haven’t really been able to find any detailed information on the effects of elemol. My guess is that this is probably the main sedative in action.

Eucalyptus oil is a known sedative with 5-10 ml producing significant CNS depression. Eucalyptus oil is about 70% 1,8-cineole (eucalyptol). So this is a possible candidate for the sedation.

Look at these quotes:

“As a mild sedative, Lemongrass's myrcene is an effective relaxant that acts as central nervous system depressant”

“Our study showed that citral, limonene and myrcene presented sedative as well as motor relaxant effects”

It looks like pretty much all of the compounds I listed other than elemicin are sedatives. I’m not sure of alpha-phellandrene or elemol. The question is, which one of these known sedatives are active at such a small dose? And how can they be removed?

 

[69ron]

Here’s the XLogP data on some of the compounds present in elemi oil.

- Carvone                  XLogP3-AA 2.4
- Methyl eugenol           XLogP3    2.5 
+ Elemicin                 XLogP3    2.5
+ 1,8-Cineole (Eucalyptol) XLogP3    2.5 
- Terpinolene              XLogP3-AA 2.8 
- gamma-Terpinene          XLogP3-AA 2.8 
- alpha-Pinene             XLogP3-AA 2.8 
+ alpha-Phellandrene       XLogP3-AA 3.2 
+ Limonene                 XLogP3-AA 3.4 
- beta-Phellandrene        XLogP3-AA 3.4 
- para-Cymene              XLogP3    4.1 
+ Myrcene                  XLogP3-AA 4.3 
+ Elemol                   XLogP3-AA 4.4

The ones listed with a + are the ones that appear in amounts likely to be active. The rest appear in very small amounts and are probably of little interest. So I’ll focus on the ones with a +.

The huge difference in polarity between that of limonene, alpha-phellandrene, myrcene, and elemol from that of elemicin shows that they should be easy to separate using the right solvent mix.

The eucalyptol and elemicin will not be easy to separate this way.

Elemicin boils at 146 C.

Eucalyptol boils at 176 C.

Eucalyptol and elemicin can be separated by careful distillation. But this is not an option for a lot of people.

 

[69ron]

Elemicin is not an alkaloid so taking harmaline with it is not really going to boost the effects much. It will alter the effects, making it sort of ayahuasca like, but it doesn’t really boost the effects much.

Isn't TMA an alkaloid? If it is indeed converted to tma shouldn't there be harmaline potentiation?

Yes, TMA is an alkaloid. If elemicin does convert to TMA as has been theorized, then harmaline potentiation is a possibility. But SWIM tried taking harmaline after the peak and didn’t notice much of a boost. There was a slight boost, but more of an alteration to the effects were noticed, rather than a boost. The combination is nice, but very different from elemi oil alone. It’s sort of ayahuasca like, as would be expected. Maybe a smaller dose of harmaline, or maybe using THH or harmine instead would provide more of a boost than an alteration of effects?

Are then any other compounds that might boost the effects of elemicin?

 

[Dorge]

SWIM still thinks people might wish to start thinking about isolating the elemicin from the elemi oil with a simple extraction using formic acid. Formic acid is easy to buy from apiary shops suppliers.

"Elemicin (4-allyl-l,2,6-trimethoxy benzene), C12H1603, constitutes the principal constituent of Manila elemi oil, in which it was discovered by Semmler1) who also gave it its name. It is found in fraction 277 to 280° of elemi oil.2) In order to isolate elemicin, the fraction in question is boiled for half an hour with formic acid. As Semmler has demonstrated by experiments made on anethol and safrol, allyl compounds remain unchanged, whereas propenyl compounds are destroyed."

not a hard thing to do... if people where working with pure elemicin we might be seeing better and more consistent results.

 

[69ron]

...not a hard thing to do... if people where working with pure elemicin we might be seeing better and more consistent results.

At some point SWIM might try that isolation tech. I’m sure pure elemicin is much better.

Here’s the XLogP data on some of the compounds present in elemi oil.

- Carvone                  XLogP3-AA 2.4
- Methyl eugenol           XLogP3    2.5 
+ Elemicin                 XLogP3    2.5
+ 1,8-Cineole (Eucalyptol) XLogP3    2.5 
- Terpinolene              XLogP3-AA 2.8 
- gamma-Terpinene          XLogP3-AA 2.8 
- alpha-Pinene             XLogP3-AA 2.8 
+ alpha-Phellandrene       XLogP3-AA 3.2 
+ Limonene                 XLogP3-AA 3.4 
- beta-Phellandrene        XLogP3-AA 3.4 
- para-Cymene              XLogP3    4.1 
+ Myrcene                  XLogP3-AA 4.3 
+ Elemol                   XLogP3-AA 4.4

The ones listed with a + are the ones that appear in amounts likely to be active. The rest appear in very small amounts and are probably of little interest. So I’ll focus on the ones with a +.

I found the following data about some of these compounds from: Page not found

Elemol: Antiacetylcholinesterase, Anticheilitic, Anticoronary, Antidementia, Antidepressant, Antigingivitic, Antiglossitic, Antigout, Antiinfertility, Antimetaplastic, Antimyelotoxic, Antineuropathic, Antiperiodontal, Antiplaque, Antipolyp, Antipsychotic, Antiulcer, Cancer-Preventive, Hematopoietic, Immunostimulant, Uricosuric, Xanthine-Oxidase-Inhibitor

D-Limonene: Anticancer (Gastric), Antimelanomic, Antitumor (Gastric), Apoptotic, Chemopreventive, Differentiator, Insecticide, Insectifuge, Litholytic, Nephrotoxic, P450-2B1-Inhibitor

Alpha-Pinene: Antiacne, Antifeedant, Antiinflammatory, Antiseptic, Antistaphylococcic, Insecticide, Insectifuge, Insectiphile, P450-2B1-Inhibitor, Sedative, Tranquilizer, Transdermal

Alpha-Phellandrene: Antistaphylococcic, Dermal, Emetic, Insectiphile, Laxative

Beta-Phellandrene: Expectorant, FLavor, Fungicide, Perfumery, Topoisomerase-II-Inhibitor

Limonene: AChE-Inhibitor, Acaricide, Antifeedant, Antiinflammatory, Antimutagenic, Antiobesity, Antiseptic, Antitumor, Antitumor (Pancreas), Apoptotic, Chemopreventive, Fungiphilic, Histaminic, Insecticide, Insectifuge, Lipolytic, Myorelaxant, Nematicide, Ornithine-Decarboxylase-Inhibitor, Ozone-Scavenger, Sedative, Transdermal

P-Cymene: Antibacillary, Antirheumatalgic, Insectifuge, Laxative, Sedative

Myrcene: ACE-Inhibitor, Aldose-Reductase-Inhibitor, Anticonvulsant, Antimutagenic, Antioxidant, Chemopreventive, Insectifuge, Myorelaxant, P450-2B1-Inhibitor

Elemol is not a sedative, if that data is correct, but actually an antidepressant, so it’s probably not responsible for the sedation at higher doses.

Alpha-phellandrene is also not listed a sedative so we can probably scratch that one off the list of sedatives.

P-Cymene is mentioned here as a sedative as well as many other sources. So this is a very possible candidate for the sedation.

Myrcene is not listed as a sedative here but is elsewhere.

Limonene is not listed as a sedative here but is elsewhere.

Eucalyptol is not listed here. It is a sedative, but the dose needed is 20 drops or more of pure eucalyptol for sedative effects, so it’s probably not the cause of the sedation. The Elemi oil doesn’t contain enough eucalyptol for it to do much at 20 drops. So it’s off the list.


So that sort of narrows it down a little. Likely candidates for the sedative effects are limonene, myrcene, and possibly p-cymene if its potent enough.

 

[Ginkgo]

Great work, ron! I have taken d-limonene supplement in rather large doses and have not noticed any psychoactive effects, so I really doubt it is responsible. But some other compounds in the oil could of course potentate the sedative effect of d-limonene.

I found this weird patent... Extracting elemicin from banana peels! :shock:

 

[69ron]

What dose of limonene causes sedation? I keep reading that it's a "known sedative", but I'm having trouble finding a dose of it that's sedating. Since it usually makes up about 50% of Elemi oil, then taking 20 drops of Elemi oil is like taking 10 drops of limonene. Is that enough limonene to cause sedation?

 

[Ginkgo]

What dose of limonene causes sedation?

I have taken 1 gram a day for extended periods of times without noting any kind of psychoactive effects. I usually feel even incredibly small doses of most compounds, so I very much doubt d-limonene alone is sedating in any amount possible to ingest from elemi oil.

 

[polytrip]

I think eucalyptol is a sedative in far lower amounts.
I once ate a bit too much of a candy that had eucalyptus in it and as a result i became a bit drunk. I wanted to experiment with it to see whether eucalyptus had some possible alcohol substitute in it (i was 13 years old then) and took some drops of eucalyptus-oil. The effects where identical. The only thing is that eucalyptus contains hydrogen-cyanide besides other stuff, so i don't know if that could have something to do with it as well. Oh, and a few drops too much of eucalyptus oil is definately unpleasant. It causes nausea and is NOT a good alcohol substitute.

 

[69ron]

What dose of limonene causes sedation?

I have taken 1 gram a day for extended periods of times without noting any kind of psychoactive effects. I usually feel even incredibly small doses of most compounds, so I very much doubt d-limonene is sedating in any amount possible to ingest from elemi oil.

That's kind of what I thought. I know a lot of people take limonene supplements and I never heard them say it was sedating. So the dose needed must be very high.

So that helps to narrow it down. We can scratch limonene off the list of sedatives. That leaves us with myrcene, and possibly p-cymene, as likely causes of the sedation, unless some of the other compounds present in very small amounts are super active.

Still, it’s possible that elemicin itself is causing this sedation. Some compounds are stimulants at low doses and then sedatives at higher doses. But still, all the references I’ve seen list it as a stimulant or antidepressant, not a sedative, so I’m more inclined to believe something other than elemicin is causing the sedation at higher doses.

Myrcene (XLogP3-AA of 4.3) should be easy to remove. It’s far more non-polar than elemicin is (XLogP3 of 2.5). Water should be able to dissolve elemicin far better than myrcene.

I wish I had detailed solubility information for elemicin. I tried to find it. I can’t find it anywhere. It’s XLogP3 is 2.5 which is the same as that of DMT. DMT is often said to be insoluble in water, however you can absorb freebase DMT into water if enough is used because it is slightly soluble in water. That’s why you can’t precipitate DMT easily in water.

It’s possible that methanol or DMSO can be used to separate myrcene from elemicin. These are polar enough that they should have a harder time dissolving myrcene.

Heptane is insoluble in methanol. Heptane has an XLogP3 4.4, which is very similar to myrcene, so it’s likely that myrcene is insoluble in methanol.

DMSO is insoluble in heptane (XLogP3 4.4), ethyl ether (XLogP3 0.9), and xylene (XLogP3 3.2). So it’s very likely that myrcene is completely insoluble in DMSO. But elemicin (XLogP3 of 2.5) might also be insoluble in DMSO or have difficulty dissolving in it. However DMT (XLogP3 2.5) is highly soluble in DMSO, so who knows.

A mix of water and ethanol at the right ratio can probably dissolve elemicin without dissolving myrcene.

By using methanol, I’m pretty sure para-cymene, myrcene, and elemol will either not dissolve at all in it or dissolve very poorly in it. That would knock of a considerable amount of the oil.

 

[69ron]

I think eucalyptol is a sedative in far lower amounts.
I once ate a bit too much of a candy that had eucalyptus in it and as a result i became a bit drunk. I wanted to experiment with it to see whether eucalyptus had some possible alcohol substitute in it (i was 13 years old then) and took some drops of eucalyptus-oil. The effects where identical. The only thing is that eucalyptus contains hydrogen-cyanide besides other stuff, so i don't know if that could have something to do with it as well. Oh, and a few drops too much of eucalyptus oil is definately unpleasant. It causes nausea and is NOT a good alcohol substitute.

How long did the effects last? Did it come on fast?

 

[polytrip]

I think eucalyptol is a sedative in far lower amounts.
I once ate a bit too much of a candy that had eucalyptus in it and as a result i became a bit drunk. I wanted to experiment with it to see whether eucalyptus had some possible alcohol substitute in it (i was 13 years old then) and took some drops of eucalyptus-oil. The effects where identical. The only thing is that eucalyptus contains hydrogen-cyanide besides other stuff, so i don't know if that could have something to do with it as well. Oh, and a few drops too much of eucalyptus oil is definately unpleasant. It causes nausea and is NOT a good alcohol substitute.

How long did the effects last? Did it come on fast?

It took about the same time as strong alcoholic beverages take, to start to work. The peak was at the beginning and the duration was dependant on the dose. At larger nauseating dose, the peak lasted for more than 30 minutes but in small amounts it was just 15 minutes. Then it started to fade, but there was a lingering sense of sedation, a sort of very slight hangover feeling, not like with alcohol but more like a numb sleepy feeling, that lasted for more than an hour. I don't exactly remember how long, but i remember it didn't last all through the day.

 

[69ron]

Here's a clip on eucalyptus oil side effects:

Can cause depression of conscious state, drowsiness, unconsciousness, vomiting or ataxia. Ingestion of eucalyptus oil caused significant morbidity in infants and young children. Significant depression of conscious state should be anticipated after ingestion of 5 mL or more of 100% oil. Minor depression of consciousness may occur after 2-3 mL.

It's stating you need 2-3 ml of it to cause minor depression. Eucalyptus oil is normally 70% eucalyptol while elemi oil is only 2.5% eucalyptol. Assuming that information above is accurate, there’s just not enough eucalyptol present in elemi oil at 20 drops if 2-3 ml of pure eucalyptus oil are needed for "minor depression".

I know you're saying less than that is needed. Perhaps you're right and that info above is not. I don't know. I have never used eucalyptus oil internally.

 

[Ginkgo]

Remember that a 13 year old might be way more susceptible to the effects than adults. Considering 2 mL of 70% eucalyptol is sedating and elemi oil only have 2.5%, one would need 56 mL of elemi oil to induce the sedating effects of eucalyptol.