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How to isolate Telepathine aka Norharman & Harmalol?

Migrated topic.
My understanding is that telepathic was the name originally given for an alkaloid mixture that was later identified to contain two distinct alkaloids which became named harmine and harmaline.

Norharman and harmalol are found in decent amounts in Russian olive, in Tribulus the amounts are so low that it is not worth pursuing. Isolating them can be tricky, they are alcohol soluble but might not be accessible using AB and Manske methods.
 
iirc "telepathine" was the name they gave harmine after using it via ayahuasca in the amazon... until they realized the chemical was the same one that had already been identified in other plants as harmine
 
en.wikipedia.org

Harmala alkaloid - Wikipedia

en.wikipedia.org en.wikipedia.org
Wikipedia said:
Telepathine was originally thought to be the active chemical constituent of Banisteriopsis caapi, a key plant ingredient in the preparation of ayahuasca; a sacramental beverage from the Amazon. This isolated chemical was so named because of the reported effects of Ayahuasca among the indigenous users, including: collective contact with and/or visions of jaguars, snakes, and jeweled birds, and ancestral spirits; the ability to see future events; and as the name suggests, telepathic communication among tribal members. It was assumed to be a newly discovered chemical at the time, however, it was soon realized that Telepathine was already more widely known as "harmine" from its previous discovery in Peganum harmala (Syrian Rue).
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Alkaloids of Banisteria caapi and Prestonia amazonicum said:
Three name, telepathine, yageine (yajeine) and banisterine were assigned to the alkaloids isolated by early workers.
...
We have recently had occacion to examine this plant anew
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In our hand Banesteria caapi "Ayahuasca" has yielded harmine (I) as its major alkaloid. We have found in addition lesser quantities of harmaline, and a third alkaloid, previously undescribed
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Tetrahydroharmine appeared to be the only likely alternate structure
...
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Kind regards,

The Traveler
 
AlbertKLloyd said:
My understanding is that telepathic was the name originally given for an alkaloid mixture that was later identified to contain two distinct alkaloids which became named harmine and harmaline.

Norharman and harmalol are found in decent amounts in Russian olive, in Tribulus the amounts are so low that it is not worth pursuing. Isolating them can be tricky, they are alcohol soluble but might not be accessible using AB and Manske methods.
Click to expand...

I drove 4 hours last summer to camp at s pot and harvest a big bag of russian olive. The usual precipitation teks did not yeild any usable ammount of harmalas at all. I know a handful of others who have had success with brews and alcohol extracts and said the potency was at least on par with caapi leaf for the leaves..and that bark was comparable to vine..

So I would def try a differet tek from manske or base precip. I used all my stash with that one tek and then gave up and left it in the fridge for too long. Oh well, Im going back this year for more. And I was smart enough to harvest seed :) The only russian olive I have seen near in my area is on private property so that sucks.
 
jamie, if there was no manske or base-precipitation evident with the russian olive tree chances are there wasn't much to begin with in your material.

I think the most prudent think to do is to check some extract (aqueous, alcoholic whatever) under UV; I believe it to be almost impossible for harmalas to be there and not fluoresce.
 
If you take a look at the literature I attached in the E. umbellata workspace you'll see that the %alk is incredibly low. Like sub 1% for the total alkaloid content (consisting of like three or four main alkaloids iirc), with each alkaloid being somewhere around .2-.3%. I did not get any results until I started working with much larger quantities of material. Additionally, it is worth noting that there is no harmine/harmaline, afaik, in E. umbellata or E. angustifolia.
 
Harmalol.svg


I think due to the hydroxide group in harmalol, it's going to be quite water soluble, so it will probably stay behind when precipitating harmalas, but yeah as others said it seems to be in very low amounts. Also, harmol and harmalol are formed in the body when consuming harmine and harmaline (source: jordi riba talk at psychedelic conference in amsterdam)
 
The real issue here is it's has a dipolar ion state just like bufotenine. Base treat-ment will deprotonate that arylhydroxyl group forming a phenolate like ion. Best bet would be column chromatography to obtain a sample and see if it can be worked with in other ways.
 
For reference I am looking specifically for norharman/harmalol, primarily due to norharman's KYNA metabolite inhibiting effects (kynurenic acid).

It's a very good target for nootropic cognition enhancement.


Thanks guys, this info is very good, exactly the kind of stuff I'm looking for.
 
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