Is cinnamolaurine from sassafras an active psychedelic?

[69ron]

Is cinnamolaurine an active psychedelic? This is an alkaloid found in sassafras. In doing tests with sassafras that has the safrole removed, SWIM found the effects are more psychedelic. He removed the sassafras by washing the sassafras with MEK. Cinnamolaurine is an alkaloid, likely as a salt in the root, and should probably not be soluble in MEK, so sassafras washed with MEK is likely to have the safrole removed but not the cinnamolaurine.

Does anyone have any detailed information about cinnamolaurine?

I’ve attached a picture to this post showing the following and how they related to each other:

* PMA (an active synthetic psychedelic alkaloid)
* Tyramine (a non-psychoactive alkaloid found in San Pedro and other similar mescaline bearing cacti)
* Cinnamolaurine (one of the few alkaloids found in sassafras)
* Norcinnamolaurine (one of the few alkaloids found in sassafras)
* MDMA (an active synthetic psychedelic alkaloid)
* Safrole (the main volatile oil sassafras)

As you can see, cinnamolaurine is almost like MDMA or safrole with tyramine or PMA attached to it at the other end.

 

[69ron]

Here are some XlogP numbers:

PMA has an XLogP3 of 1.8
Tyramine has an XLogP3 of 1.1
Cinnamolaurine has an XLogP3-AA of 3.2
Norcinnamolaurine has an XLogP3-AA of 2.8
MDMA has an XLogP3 of 2.2
Safrole has an XLogP of 3.0

PMA (4-methoxyamphetamine) is able to enter the brain and is hallucinogenic at doses of 50 mg or more. This appears in TiHKAL as “#97 4-MA”.

Tyramine is said not to be able to enter the brain because of its low XlogP, and so it only produces bodily effects.

Cinnamolaurine found in sassafras root bark looks like a possible hallucinogen to me. The high XLogP3-AA suggests that it will cross the blood brain barrier easily.

Norcinnamolaurine found in sassafras root bark also looks like a possible hallucinogen to me. The high XLogP3-AA suggests that it will cross the blood brain barrier easily.

MDMA (3,4-METHYLENEDIOXY-N-METHYLAMPHETAMINE), more commonly called ecstasy, is hallucinogenic as doses of 80 mg or more. This appears in TiHKAL as “#109 MDMA”.

Safrole is not an alkaloid, and should not produce hallucinogenic effects despite its high XlogP. It may however get converted in the body to an active substance (this is debated).

I have searched and searched and cannot find anything talking about the effects on man of cinnamolaurine or norcinnamolaurine. If anyone has any details about the effects of either, I would love to know about it.

 

[burnt]

This compound is found in cinnamon (hence the name). Never heard of anyone getting high off cinnamon...

But maybe looking into cinnamon as a source would lead to something interesting. Most people consume cinnamon in low doses or cooked so the compound wouldn't be present in significant concentrations.

 

[69ron]

Yes, cinnamolaurine was originally isolated from cinnamon. The molecule looks unstable to me, and probably doesn’t withstand cooking. If this is an active alkaloid in sassafras, SWIM’s test showed sassafras was pretty inactive if heat was used to make tea form it, indicating that the actives in it are either not heat stable or vaporize away easily.

I’ve never heard of people consuming large amounts of cinnamon. I also don’t know how much cinnamolaurine is present in cinnamon. It may be too small to be of any significance. Or maybe there’s a ton of it and it’s simply inactive.

Cinnamon is extremely unpleasant if eaten in large amounts causing extreme nausea, so I doubt people would ever use large doses of it to test for activity. At about 1 tsp, it makes you seriously nauseated.

I once saw a thread of people betting each other they could eat a teaspoon of cinnamon and keep it down. No one could do it. They all puked. So I just can't imagine people using larger doses to get effects from it if they could. But maybe someone has tried it. I just can’t find such a report anywhere.

 

[۩]

A tsp of cinnamon? I consume about that or more with breakfast with no nausea what-so-ever.

 

[69ron]

I like cinnamon. I love cinnamon toast. I never tried 1 tsp at once though. But I think I could probably eat that much too. Maybe I remember the thread wrong. Maybe it's 1 tablespoon at once and not 1 teaspoon? I'll have to try to find the thread again so I can get more accurate details on it.

Considering the possible psychoactive impact of cinnamon, I saw this quote on another forum talking about using cimmanom to enhance the effects of calamus!

That's what I get, with light color shimmering, when I smoke a not so freshly dried root from the local pharmacy. It's even better to add a some clove. Asrone+eugenol is great . One can also add cinnamon, but I find it to be just like clove in its effects, and clove is more tasty.

 

[narmz]

In doing tests with sassafras that has the safrole removed, SWIM found the effects are more psychedelic.

Could SWIY go into some detail about these tests? What were these psychedelic effects? What were the effects when the safrole was not removed?

 

[69ron]

Here's the eating pure cinnamon link. As I read it again, it’s unclear as to the exact dose that makes you purge.

http://forum.ebaumsworld.com/archive/index.php/t-66824.html

 

[69ron]

In doing tests with sassafras that has the safrole removed, SWIM found the effects are more psychedelic.

Could SWIY go into some detail about these tests? What were these psychedelic effects? What were the effects when the safrole was not removed?

Before the safrole was removed, the effects of a cold water extract were like that of a sedating but mild MDMA experience. After a good portion of the safrole was removed by washing with MEK, a cold water extract produced effects that were stimulating, and similar to 50 micrograms of LSD. There seemed to be light visual effects at the peak when 20 grams of root was used.

The effect is long lasting, about 20 hours. Tolerance to the effects builds up pretty rapidly though. So you need to ingest the cold water tea in one shot, not spread throughout the day. As SWIM is extra sensitive to things like this, others might need 40 grams or more to feel it. For SWIM 20 grams is very obviously mildly psychedelic. I’m using the term “psychedelic” loosely though. The visual effects were very mild. The main effects were stimulation, euphoria, tingling sensations, special awareness alterations, etc.

For more details see this thread:

Sassafras a hallucinogen? Really?

 

[burnt]

the essentials oils in cinnamon are probably what causes the nausea some report after ingesting too much. these could again be removed by gentle distilling (which might destroy other compounds) or maybe those washes too.

But yea its not worth going further unless we can find the concentration of the alkaloids. it might be too low...

 

[lysurgeon]

Antimalarial benzylisoquinoline alkaloid from the rainforest tree Doryphora sassafras - PubMed

Mass-directed isolation of the CH(2)Cl(2)/MeOH extract of Doryphora sassafras resulted in the purification of a new benzylisoquinoline alkaloid, 1-(4-hydroxybenzyl)-6,7-methylenedioxy-2-methylisoquinolinium trifluoroacetate (1), and the known aporphine alkaloid (S)-isocorydine (2). The...

www.ncbi.nlm.nih.gov

Cinnamolaurine, at least conjugated with trifluoroacetic acid, possesses antimalarial properties, and was tested for toxicity on human liver cells. Looks good. I don't know about any of you, but I have personally noticed that a few MAOIs are antimalarial - syrian rue and methylene blue come to mind - and I also experienced taking a sassafras tincture with some morning glory CWE (trying for the scarce aldehydes) and experienced a two-fold increase in duration of morning glory. MAOI activity is something I could see happening here. And it would account also for the mild psychedelic effects I have also experienced from cinnamolaurine-containing plants.