Several interesting alkaloids from common plants...

[DL-ark]

Ok, so I have been interested in the concept of a legally owned garden of entheogens and even just well known psychoactive plants. I started this project with a very simple project - Chamomile with some peppermint and spearmint for flavoring the tea. This was just to see how well I could manage an herb garden before spending money on buying other plants. Anyway, I was curious as to what alkaloids were in these plants - I already knew that Menthol was in peppermint, and a quick look at the alkaloids/flavonoids in chamomile revealed that apigenin is responsible for it's relaxing effect (Apigenin is actually a very pharmacologically interesting molecule). Anyway, a search on the alkaloids of spearmint revealed this document: http://journal-phytology.com/index.php/phyto/article/viewfile/11450/5855 . It explains a methanolic extract of Spearmint, and then shows a table of the constituents of such an extract. Now, look at the third 'constituent' - anyone who has knowledge of how psychedelic phenethylamines like DOM and 2-cb work will recognize the formula - It is a DOx analogue. I call it DOMOS (DO - Methoxysulfonyl). It perfectly fits David E. Nichols description of a psychedelic phenethylamine/amphetamine. It's structure seems to pass most drug-likeness/BBB filters. So why haven't we heard of it? The possibility that Spearmint, of all plants is psychedelic is truly spectacular.

I have another plant for you. I live in a region of the universe that occasionally will self-cultivate California poppies. These are already known to be Benzodiazepine receptor ligands, and have also noted activity on the 5HT1 and 5HT7 receptors. This was speculated to be due to the alkaloid N-Methyllaurotetanine - an Aporphine analogue. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=16573
You should be able to see its resemblance to Lysergic Acid, or any other Ergoline. Aporphine itself produces visual enhancement and closed eye visuals.

What do you guys think? Am I on to something or is this all just ridiculously desperate?

 

[sekio]

I'm going to call that an error in their analysis... spearmint doesn't contain amphetamines, that's just the closest match the GCMS could come up with. It also says spearmint contains 0.12% 4-methylamphetamine. Somehow I doubt it.

In fact the analysis is really lazy here. 3-octyne-2-one in spearmint? Excuse me? More like menthone. The authors seem to just report the suggested compounds with no further verification.

The possibility that Spearmint, of all plants is psychedelic is truly spectacular.

It's not, though. People eat mint jelly with their lamb.

Aporphine itself produces visual enhancement and closed eye visuals.

It's also used in veterinary medicine to make animals vomit if they've eaten something they shouldn't. It would otherwise be a good drug for some dopamine related disorders... you're correct that it resembles lysergic acid in that respect. They both share dopamine receptor affinity.

 

[RecoveringPothead]

These are good herbs with medicinal qualities but I'm going to have to agree with sekio.

Of course there are a variety of legal psychedelic plants like morning glory and salvia. Morning glory is very common in fact and is sold at most garden centers as seeds which you can plant.

Then there is kratom which acts like an opiate.

Interesting speculation though.

 

[DL-ark]

I'm going to call that an error in their analysis... spearmint doesn't contain amphetamines, that's just the closest match the GCMS could come up with. It also says spearmint contains 0.12% 4-methylamphetamine. Somehow I doubt it.

In fact the analysis is really lazy here. 3-octyne-2-one in spearmint? Excuse me? More like menthone. The authors seem to just report the suggested compounds with no further verification.



It's not, though. People eat mint jelly with their lamb.



It's also used in veterinary medicine to make animals vomit if they've eaten something they shouldn't. It would otherwise be a good drug for some dopamine related disorders... you're correct that it resembles lysergic acid in that respect. They both share dopamine receptor affinity.

I agree that the study of spearmint looks awful sloppy (typos exist). However what you said about them listing Methylamphetamine as a possible alkaloid - I would like to clarify that beta, alpha - dimethyl phenethylamine (beta methyl amphetamine) is different from N-methylamphetamine (What we call methamphetamine). Although the study notes a chemical called "Phenylethyamine, p, a-dimethyl-" I can only assume they mean phenethylamine, β, α -dimethyl.

As for your mint jelly comment - I don't mean to be overly optimistic but it is possible that the process of extracting the mint flavor from spearmint is performed in such a way which would remove the amphetamines or perhaps the extract is in such a low concentration that effects are not felt (this would be the only explanation since spearmint is so widely used in teas, candies etc). However, as you have stated the study looks very odd now that I look at it again.



So, do you think N-methyllaurotetanine would be more active than aporphine? Is it possible that it's additional structural elements would create a less nauseating effect. I suppose euphoria would be possible aswell with dopamine agonists. I would also like to remind you that Aporphine is a 5HT1A and 5HT7 agonist. Extracts of California Poppies are also 5HT1A and 5HT7 agonists. I think this atleast suggests that N-Methyllaurotetanine is active, what hasn't been tested is this chemical's activity on Dopamine receptors.


I actually posted about California poppies a bit ago: http://www.bluelight.org/vb/threads/719131-discussion-of-California-Poppies-(escholtzia-californica)

 

[DL-ark]

These are good herbs with medicinal qualities but I'm going to have to agree with sekio.

Of course there are a variety of legal psychedelic plants like morning glory and salvia. Morning glory is very common in fact and is sold at most garden centers as seeds which you can plant.

Then there is kratom which acts like an opiate.

Interesting speculation though.

I will certainly be planting morning glories, its actually next on my list. I am waiting to see how I do with my mints since I have heard that Salvia is best treated like a mint.

 

[Synaps3]

I'm not too much of a chemist, but your mention of Apigenin jogged my memory about the similarities to methaqualone I noticed. I mean, it's not that similar, but similar enough that I think some interesting GABA-ergic compounds could be created from possibly sharing certain features from those two.

 

[DL-ark]

I'm not too much of a chemist, but your mention of Apigenin jogged my memory about the similarities to methaqualone I noticed. I mean, it's not that similar, but similar enough that I think some interesting GABA-ergic compounds could be created from possibly sharing certain features from those two.

Whats very interesting is that it may not only agonize gaba a but it also agonizes benzodiazepine receptors AND is a second order positive allosteric modulator. This means it potentiates itsself in theory. I will also say that chamomile tea is somewhat euphoric. More euphoric than alprazolam in my opinion, although benzos arent known for being particularly euphoric

 

[Hammilton]

P is for para, not an error for beta, which is why Sekio referred to 4-methylamphetamine.

 

[DL-ark]

Ah ok, my mistake, I wasnt aware of "para"