Well, this is going to be a long post, I've got quite a lot of information to put into this and I'll probably end up rambling. The way I got interested in this molecule, cinnamolaurine, started out at a gathering in New Mexico about a year and a half ago. I was on a mission to acquire a drum, and met a girl who called herself Vanilla Bean, and after working out a trade with her, she gave me and my girlfriend a white powder that she dissolved in some green tea, and told us it was a "shamanic extract" of sassafras roots, and that it had an ecstasy-like effect only it was much more subtle and chill. That's her description. We drank the tea and tasted a bit of powder on the rim of the glass and it was very bitter. My girlfriend and i were quite surprised to feel within about an hour or so a growing empathy and openness, and only a very slight bit of distorted vision, altogether giving me feelings reminiscent of MDMA only much more natural feeling and totally missing the jaw-clenching stimulant-like activity. In fact, we were able to sleep within about 4 hours of ingesting the powder, and it was very very comfortable.

About 1 or 2 months later, in the woods in Alabama, I stumbled upon a nice-sized sassafras tree, having learned to recognize them by their unique leaves and of course the "scratch and sniff" test of the roots, and being familiar with the smell of root beer. I asked the tree for some roots, tree asked me why, my answer was to address the ills of my spirit, and its response was to tell me how much to take to split with 3 people, myself, my girlfriend, and my mom. This was the most outspoken mental interaction I experienced in working with the sassafras tree other than while feeling its effects, all times I harvested after this I just sorta paused to see if the tree would protest before I collected roots. I always made sure that I was not endangering a colony by collecting roots. Anywho - I chopped up the roots and the root bark, and boiled them in a pot of water with lemon juice added for about 2 hours, drained the tea, boiled for another hour or so and kept on until the tea stopped getting appreciably darker, reduced the tea to approximately 3 1/2 cups, split it into three glasses, added lemon and honey and sugar and other stuff to improve the taste. The effect was nausea within the first hour, and increased empathy in the second hour, visual distortions and noticeable 2D spinning visuals that resembled flowers but were made of stuff that my eyes were seeing (like a superimposed algorithm). The overall feeling and nature of the effects and the subtlety were more or less identical to the extract we had tried previously in New Mexico.

My instict was that the famous ingredient of sassafras roots, safrole, was the responsible agent for this psychoactivity. Thinking along the lines of phenylpropanoid oils, I began to research other plants that contain psychoactive phenylpropanoids, such as nutmeg (has dreamy psychedelic effects, which seem to be similar to the effects of MMDA which causes "brain movies" only minus the amphetamine-effects), and calamus and wild ginger(having psychedelic effects which seems similar to TMA-2), and more recently reading about elemi (having psychedelic effects which could be similar to TMA)....so it made sense that ingesting some extracted form of safrole which is crystalline at room temperature would cause MDA-like effects only of course minus the amphetamine-effect. My reading about safrole however led me to believe that there is no way that it would ever exist as safrole at room temperature and not be a yellow oily liquid that smells very strongly of root beer. The physical properties of the white crystalline bitter-tasting solid which I would eyeball from memory to say it takes around 100-150mg of the stuff to be strongly active are definitely different from the physical properties of safrole. My research into the pharmacological properties of safrole indicate that it is a sedative and an anaesthetic.

So I found a website called Dr. Dukes Phytochemical Database. I browsed through the list of chemicals reported for the plant sassafras albidium, and came up with a number of what I called "substances of interest" among them safrole, 5-methoxy-eugenol, apiole, anethole, asarone, elemicin (all of these are phenylpropanoids), piperonylacrolein (safrole-aldehyde pretty much), coniferaldehyde (3-oh-4-meo-phenylpropaldehyde) both of these also phenylpropanoids and aldehydes, and reticuline (also an opium alkaloid) and cinnamolaurine (the compound that drew my attention when I searched the structures of all these molecules on pubchem and google/wikipedia complex), also thujone. I was surprised by the sheer number of molecules that have been proven psychoactive already (thujone, elemicin), have been speculated to be the psychoactive principle in another plant(thujone, asarone, elemicin) , or simply have a structure that looks like it probably is psychoactive (cinnamolaurine, reticuline, 5-meo-eugenol, safrole).

I experimented with tinctures while I was still on the fence about whether I was trying to extract safrole or alkaloids, so therefore used a technique that would theoretically extract both. With this tincture, I experienced what I would call a very mescaline-like mindset and with a bit of physical stimulation and also shortness of breath, but almost totally lacking in visuals. Each time I made the tea, the effect was less, even when using the same amount or more of the root/root bark. I did perform an extraction procedure on some root/root bark while I was still in Alabama, but at the time I had so many projects going on and I have a bad habit of not labelling bottles that the result is that I wound up with a white powder that I tasted and it was bitter and produced low threshhold effects - I used tea, sodium hydroxide, and naphtha, and evaporated the naphtha. I was concerned about possible contaminants because I was also breaking the golden rule of "don't be tripping while doing extractions". Lesson learned, I'm being a lot more careful now. Before I left Alabama, I collected one last batch of sassafras roots, knowing I was returning to california where sassafras trees pretty much never occur.

My interest in this pharmacological mystery continued, and as I researched more and more on the internet, I came across the nexus (you are here) and there was a thread about "is safrole psychedelic?" and in that thread mr. 69ron mentioned, much to my personal feeling of being on the right track, that cinnamolaurine is the most likely candidate for the psychoactive effects of sassafras tea. He also mentioned that heat seems to destroy the active principle, and I took note of that and have respected that in my subsequent research. Also on an interesting sidenote, I was searching for cinnamolaurine about a month or two ago and found text from an e-mail I had sent to a friend of mine posted in a thread titled "is cinnamolaurine from sassafras an active psychedelic?" which was interesting because now I know that I know someone from real life who posts here....anyhow....

I noticed that cinnamolaurine has a striking resemblance to the word cinnamon, and figured it was likely in cinnamon, though Duke's database does not show this compound being present. A google search finally turned up a PDF of three sets of experiments performed on Australian cinnamon species (2 of them) around 1969-1972 which showed that the total alkaloid content of cinnamon bark from australia is 0.01%, the dominant alkaloid is reticuline, and the other alkaloids are cinnamolaurine, norcinnamolaurine, and corydine. All 4 of these alkaloids are benzylisoquinolines. I assume that an extraction procedure that would pull one of the alkaloids would also pull the other 3.

My girlfriend came up with the idea to buy a bunch of cinnamon and perform extractions on it and test the extractions via bioassay. Now we're getting to the heart of the long-ass post I'm making! We were unable to get ahold of the same species of cinnamon tested for alkaloids in australia, so instead we got Cinnamomum Zeylanicum (I think it's an outdated latin name for Ceylon Cinnamon aka "true" or "sweet" cinnamon) and Cinnamomum Cassia ('bastard cinnamon'). Thanks to a shipping error, we received 2 lbs of each. We also got ahold of a pint of D-Limonene, which I chose as a solvent for several reasons - I wanted to know what it was like to do an extraction that smells good, I figured that a solvent that works for mescaline should work for an isoquinoline (I know its a generalization) and I was just curious to try working with a solvent that has no ties to petroleum (nasty) but instead has ties to the orange juice industry (I love orange juice). Also I was inspired by my friend's work with sassafras, which was a d-limonene soak followed by an isopropanol soak. I didn't want to accidentally destroy the alkaloids with NaOH (I'm aware that lysergic acid amides degrade to lysergic acid if treated with lye), so I bought up a bunch of baking soda to convert with an oven to sodium carbonate. And I got a bunch of vinegar, and I drink wine frequently enough to supply myself with glassware.

I began with a cold vinegar soak of 100g C. Zeylanicum, approximately 24 hours, basified slowly with dissolved Na2CO3. The first few times I did this, I created a cinnamon volcano, and the CO2 released would turn the very fatty liquid into an undying foam. These early extractions were frought with difficulty and frustration. My method was that I would add carbonate until the already pinkish liquid turned as dark as possible, then I would add d-limonene, shake, and allow emulsions to drop, allow there to be contact between the limo and water layers for up to 24 hours, separate the limonene, mix it with vinegar, shake, allow to separate, separate the layers, and evaporate the acidic liquid on a plate, then scrape that up and put it into a container. Lately, I've been working on using NaOH having decided that it's worth it to not have to deal with unending foamy emulsions, the possibility of untapped alkaloid potential with those extra pH's not reachable by means of carbonate. So far, I haven't finished my first STB extraction but the yields are looking lower than I had expected, which is sorta the theme of this whole experiment.

My reasoning for doing this research is basically to determine whether or not the alkaloids that are in common between cinnamon and sassafras (reticuline and cinnamolaurine) are responsible for the psychoactive effect of sassafras. My girlfriend's reasoning was to find out if an extract of cinnamon would be a reasonable substitute for an extract of sassafras, or really to find out if cinnamon is viable as an alternative (cheaper) plant as a source of a naturally-occurring empathogen. The results are thus far inconclusive due to the ridiculously low yields, though bioassays have occurred. My yields have been, by weight, about 30 times higher than those reported by the austalian researchers, averaging to around 0.3%, however I think that this weight of material is due to contaminants in my samples (fats from the plant that are extremely difficult to keep out of the way), and that the actual alkaloid content is either no higher or not much higher in the available species than in the australian species. It's a very messy plant extraction, lots of emulsions all the time, fats everywhere.

After several extractions on both Zeylanicum and Cassia had been performed, I performed the same process on combined sassafras root/root bark (about 35g bark to 65g root), yielding a similar amount of material that besides having a similar physical appearance, also had a very similar smell. Here's all the info I have on our bioassays:

C. Zeylanicum, 100g plant = 0.3g extract, which after a couple weeks weighed 0.2g. 0.1g put into each capsule, we each consume about 100mg extract. Unfortunately though I am interested in science and certainty, a friend came over with a blunt and fogged our results. from the notebook: "Basically our appx 100mg bioassay was heavily fogged by the hitting of a blunt. (girlfriend) could perceive no effect. I felt only a minor stimulant effect that was only very close to the threshold of the type of effect that I can imagine I feel, it was only between 1 and 2 1/2 hours after ingestion. The cassia extract has also changed mass, from 0.4g to 0.3g"

C. Cassia, 100g plant = 0.4g extract, changed mass to 0.3g - split into halves, encapsulated and split between my girlfriend and myself. "1h20m: I kinda feel a non-caffeine stimulation. 5h10m I feel that there is a mood-elevation effect. I am more able to express myself. Today is tinged with a slight discoordination in motor skills. (girlfriend) felt threshold effects as well. Cassia produced slightly more alkaloids per 100g than zeylanicum, and the total effect from 100g cassia compared to 100g zeylanicum leads me to believe cassia contains either a more favorable alkaloid profile or just plain more alkaloids."

S. Albidum, 100g plant = 0.4g extract. Split into 2 0.2g capsules, girlfriend and I each eat one. "1h20m: feels similar to cassia extract and I have the "tripping" feeling in my teeth. 2h40m: at the store I began to have mild hallucinations and motion distortion - wiggly lines - a feeling similar to a low dose of mescaline or psilocybin."

C. Cassia, 200g plant = 0.4g extract (yeah I was surprised). Split into 2 0.2g capsules, girlfriend and i each eat one. "5h - we are noting nothing."

I don't know what was up with that last one, why extracting twice as much plant material produced the same amount of extract which produced less effect than 100g plant material. I know it's still too early to draw any certain conclusions, but I do believe that cinnamon contains psychoactive alkaloids as well, just much less of them than sassafras, and I do think that the similarities between the extracts of these two plants in smell, appearance, taste, and effect, indicates (but does not yet fully confirm, as I have yet to all the way feel like "this is it" with cinnamon extracts) that at the very least cinnamolaurine and reticuline are each likely responsible for some aspect of the psychoactivity of sassafras.

I have one more big extraction planned with 600g c. cassia, going to do 3 vinegar soaks, basify with NaOH, extract each of these pulls twice with d-limonene and twice with naphptha, extract each of these sets of solvent twice with vinegar, and then the leftover plant material from those three vinegar soaks I'll soak in a strong lye solution a-la-STB and extract twice with limonene and twice with naptha. This should be thorough enough to bring out greater yield totals than 0.2g. Then I'll do a nice big bioassay and hopefully not die...although I have totally been working my dosage up very slowly mostly due to the amount available to me at bioassay time. Well, I hope this is enough information, I know there's more stuff, I'm willing to answer any questions, and I'm also willing to take advice on extraction procedures. Maybe I should post this in the "general extractions help" page, though I think I'm working my way through pretty well here.

Holy SHYTE this is a long post, maybe I should break it up into seven smaller posts?

The activity of these compounds is largely speculative. Sure nutmeg gets you high and apparently sassafrass gives people a buzz too. But none of the extract procedures outlined are in any way selective for single compounds or groups of compounds so although your research may lead to an extract that has some psychoactivity you won't be able to know what compound(s) are causing it.

Your are also putting yourself at risk by making such speculative extractions of compounds. Sure cinammon is not toxic and sassafrass in low doses is not toxic but concentrating completely unknown extracts and ingesting them isn't a good idea as it may lead to adverse toxic effects.

Plus its important to note that safrole and related compounds with terminal methylene groups are all potentially carcinogenic.

So this is interesting... now I'm about to argue that something's safe, where burnt is cautioning that it may be toxic (we used to take the opposite stances back when I first introduced limonene to this forum)... heh heh.

The procedures outlined above -should- not extract much if any safrole or other oils, as they're not really water soluble enough to make it into the vinegar layer during the last step of the procedure.

True, large doses of safrole can cause liver cancer in mice, but there's no evidence to indicate that the tiny amounts of safrole that are water soluble enough to make it into the livers of occasional drinkers of sass tea cause any problems. The only thing mentioned above that would concern me is the tincture approach, as this may concentrate potentially harmful levels of safrole, but he's no longer doing that nor suggesting that anyone else do so either.

As for the alkaloids themselves, of course one can never know anything for sure I suppose but they seem harmless enough. When you consider their source, their structure, and the (albeit limited) bioassay reports out there, there is absolutely no indication of toxicity. I say this perhaps a bit more assuredly than one would have cause to speculate based solely upon the limited evidence, as I have personally bioassayed extracts of sass and felt no toxicity whatsoever, and I'm usually pretty good at noticing toxic crap. Thanks to being hypersensitized from extensive work with the right plants (harmala, aya, cactus, etc.) I can detect synthetic additives in food, things like artificial flavorings and hydrogenated oils set off a "toxicity alarm" in my perceptual mechanisms... I can also feel when a person on the couch next to me has a cell phone in their jacket pocket and gets a text message, and have demonstrated such on more than one occasion... and while yes this is all subjective, I personally detect NOTHING dangerous or toxic about the alkaloids in question (with respect to my ingestion of sass extracts, and also my frequent habit of consuming large amounts of cinnamon, which I find to be incredibly medicinal).

That having been said, of course one is right to caution would-be experimenters when navigating uncharted territory. It would suck if someone went out and died cuz they were careless and ate 2.3 grams of sass extract cuz SyZyGyPSy said it was safe! But given what info we do know, I'd still be much more concerned about consuming toxic residue from petroleum solvents than anything naturally occurring in "sass" or "cinn" that might be extracted by the above procedures (tincture method excepted).

That having been said, as far as extraction tips, the more I think about it, the more I'm thinking one would be better off using CaOH, ala 69ron's limo cactus tek. First off, it's s'posed to be the best as far as not making fatty emulsions be such a pain in the arse, hence why it's used on cactus. Second, NaOH may generate enough heat to destroy alkaloids that are heat sensitive, unless it is reacted with water and allowed to cool first.

Everything else outlined above looks good. I like the idea of trying limo pulls followed by petrochem pulls (from a scientific standpoint, at least), though if you're gonna do it, you might as well use toluene in my opinion, as it's more of an "omnisolvent" than naptha, hence more likely to get anything that the limo might have missed (though I've yet to see anything tolly pulls that limo doesn't).

Don't get me wrong, I hate encouraging anyone to use petroleum for anything, but in this case it would be nice to have the data when it comes back and shows there's no need for it, that the limo got everything (which is what I'm predicting...).

Anywho, props to lysurgeon on some fantastic, gound-breaking experimentation. And of course, kiddies, do not try this at home... but that having been said, the above teks still seem safer to me than 69ron's reports of CWE of sass (less potential for safrole), which no one berated him for.

And as for selectivity of compounds, the above procedures (please correct me if I'm wrong) are pretty selective for ALKALOIDS, which narrows it down, then when you combine the fact that two plants with common alkaloids are being tested, well, similarity of effects would indicate possibility of common alkaloids being involved, no? Granted, nothing conclusive... but a good place to start, right? It's a long way from speculation to proof, and one has to start somewhere...

Also worth mentioning that certain groups of "hippies" have been consuming "sass" for some time now, and while many things have probably been dispensed by that name, I've yet to hear a bad report about natural sassafras alkaloids - again not conclusive, but my gut feeling tells me moderate research with this stuff is safe... MUCH safer than crap like MDMA for instance, which I'd LOVE to see sass alkaloids turn out to be a natural replacement for. Swim can't stand molly's amphetamine jitters and serotonin depletion, but feels quite healed during and after ingestation of naturally occuring sass alkaloids. IMO if this replaced molly at the festival scene, you'd have a lot less bickering on the last day of the festival from kids with depleted 5ht systems, and a lot more genuine exchange of intellectually and emotionally RELEVANT information than the ramblings of "psychedelic tweakers" that currently dominate too many campfire circles for my own personal taste... just my .02 USD.

Now, speaking of ramblings, I'm going to end mine for the time being

And brother burnt, much love to you... haven't argued safety or metaphysics with you for some time, and am realizing I've quite missed it

I don't think chowing on cinnamon is any way unsafe. Even sassafrass roots at the doses normally taken seem fine according to the limited data available in humans.

But taking 1-kg of roots form any plant and extracting it down to 1mL of a semi unknown substance and then eating that substance because one follows an "alkaloid" extraction procedure thinking its automatically safe is not always true.



No offense but this has nothing to do with legitimately determining toxicity. Sorry I ain't gonna let that slide

I have a bottle of cinnamon zeylanicum oil, and the one time I had some sublingually I did feel a very mellow mescaline like effect..this was a very low ammount of cinnamon oil that was added to water as a mouthwash...

Kathlene Harrison has a talk called "spirit in nature" or something like that where in one part she mentions that the mazatecs she worked with always use cinnamon tea after mushroom ceremonies and they continue to drink it for the next day due to something like its warming or opening effects...this is very interesting, since it is not a traditional plant of that region..they adopted it's use...

I have much more directions I've looked into regarding the activity of these compounds. I looked into benzylisoquinolines and found that some are used medicinally, such as papaverine (also an opium alkaloid), tretoquinol (one that somebody was clearly inspired by mescaline's structure to invent) - also, protopine (another opium alk) is not necessarily a benzylisoquinoline but it contains mostly the same structure, and Laudanosine (another opium alk) is a benzylisoquinoline which apparently lowers the seizure threshold, therefore can induce seizures if taken in sufficient quantity. Each of these compounds has a different pharmacological effect, which seems to be a staple of the isoquinolines, extremely variegated pharmacology for a single class of molecules. Considering the possibility that Corydine, the only cinnamon alkaloid that seems to have any pharmacological research behind it, can cause "strychnine-like" convulsions leading to death in rats, has kept me from jumping up the dosage. Believe me, I am under no such illusion that what I am doing is safe. I'm fully aware of my own canary-in-a-coal-mine-ness. I am also under no fear-induced belief that what I am doing is inherently dangerous. I'm also not recommending that anyone else do what I do. However, if anyone out there does do what I do, I'd like to hear about it.

And as SyZyGyPSy said, the process that I'm putting the plants through should protect against the oily constituents ending up in the extracts. First, a compound must be in the plant I'm extracting from. That eliminates most matter in the universe. Second, a compound must be soluble in acidic water. Once again, much material is eliminated just by this step - oils like cinnamaldehyde (the main aromatic/oily constituent of cinnamon) are not soluble in water or acetic acid, so if they end up in the next step then it's due to my failure to separate the plant material from the liquid extract, or some oil manages to escape the plant and hang out as a small floating layer on top. Third, a compound must not as soluble in basic water as it is in a nonpolar solvent. Fourth, a compound must be more soluble in acidic water than a nonpolar solvent. So altogether, the compound has to be in the plant, soluble in acidic water, less soluble in basic water than a nonpolar solvent, and more soluble in acidic water than in a nonpolar solvent. Pretty much, the compound has to be an alkaloid or an alkaline substance. In my STB experiment, the solvent turned very yellow, and smelled strongly of cinnamon and solvent. I'm pretty sure that cinnamaldehyde is soluble in naptha and limonene due to this experiment. And the acid extract from these solvents, when dried, smelled not of cinnamon, nor solvent, nor vinegar. The smell of cinnamon is a dead giveaway that you have cinnamaldehyde, just as the smell of root beer is the dead giveaway that you have safrole.

Thank you for your responses, all of you! And to tie up a little loose end, I may or may not have explicitly stated this, but the idea behind the experiments is to find out if an a/b/np/a extract of cinnamon will produce similar effects to an a/b/np/a extract of sassafras, being that they both contain the speculated upon molecule cinnamolaurine. My main concern is that cinnamon might contain high enough concentrations of corydine compared to cinnamolaurine, norcinnamolaurine, and reticuline, that doses that approach the psychoactivity of sassafras might also introduce problems such as I've read being attributed to corydine. But I do believe that I have felt something at a threshold level that is indeed similar to a threshold level of sassafras, I am pretty much just doing one more experiment to take a high enough dose to feel more certain about the results. And I'll be doing that carefully.

I love you all.

what about a methanol or ethanol extract? I don't mind consuming safrole. Would either of these grab the goods?

I know of someone who did a d-limonene soak to remove the safrole, then an isopropyl alcohol extract to pull the alkaloids, resulting in some material that required at least 1g per person to experience what were still mild effects. I think that just way too much stuff is soluble in alcohols for them to be an efficient means of extracting alkaloids from such a compound-rich plant as sassafras or cinnamon. I'm interested in doing a nice big-amount-of-plant-material acid/base/nonpolar/acid extraction with sassafras roots. Maybe someday. I've got that 600g cassia extract going, I'll be doing the first xylene pull (I settled on that solvent for this experiment, which is a nasty smelling carcinogenic and petroleum-industry-supporting decision I know better than to make now...limonene is the way!) I will post more info when that extraction is complete.

Well, it has been quite a while since I did any experimentation with this plant. By now my last tests were about 10 months ago. I have previously had success using very dilute naoh/koh with naphtha to yield freebase solids. Every other time using hydroxides resulted in failure to extract. And thanks to the discussions here in response to a thc extraction I posted, I came to understand the nature of phenyl rings bearing hydroxyl groups relative to strong alkaline agents.

I also had problems working with psilocybe alkaloids and hydroxides, and I have read through anadenanthera extractions and observed people dealing with similar problems. Compounds bearing a hydroxyl group on an aromatic ring generally will form water-soluble salts with sodium ions, especially with sodium hydroxide.

Having had a nearly zero extraction result from working with sassafras and sodium hydroxide, things remain consistent. I have had success using sodium carbonate with sassafras and with cinnamon. In all these cases the solvent was d-limonene. I think the tek that has been worked out for anadenanthera may well work for other phenol-bearing alkaloids. Certainly next time I acquire any quality sassafras roots, I will try extraction using carbonate, acetone, citric acid, etc. I also have heard about a method of selective crystallization of sassafras alkaloids from 95% ethanol solution. I will also try this someday.

Reference anyone?

Another thing to try would be, should you have pruned a bay tree (Laurus nobilis), strip the bark off the branches and twigs (much easier when fresh!), dry, powder and do as you will. Definite stimulating/euphoric effects have been noted at surprisingly small doses.

DO NOT CUT THE BRANCHES OFF ANY OLD BAY TREE JUST BECAUSE YOU'RE LOOKING FOR FREE DRUGS! At least have the decency to caringly prune a tree you're looking after.



Bay bark will of course also be toxic given a large enough dose so proceed with caution if you decide to explore this relatively unknown area. As a spice it's a bit like cinnamon but considerably more stimulating.