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Harmine from Passiflora Caerulea extraction results

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_Trip_

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My country made harmala illegal years ago and as of a few months ago banned Syrian Rue for import. Leaving B. Caapi as the only viable source of Harmala alkaloids. As many live in colder climates B. Caapi isn't the easiest to grow and Syrian Rue itself can be very fussy to grow. This left me reading articles on passiflora as a possible alternative.


According to the study listed below Passiflora Incarnata vs Passiflora Caerulea, harmine was extracted. Passiflora Incarnata yielded .0057mg/g and .013mg/g in the 2 samples making it a poor choice for harmine. However, Passiflora Caerulea produced roughly 10 times the amount at .102% still a poor choice for an extraction. These results were from the flowers and leaf of the vine. This got me thinking as I remember reading somewhere the fruit can contain 4 times the amount of alkaloids in passiflora.

I did a preliminary extraction. I dried 10g of Passiflora Caerulea seeds (the red fruit was also included) and 30g of the outer fruit 'husk' I conducted two extractions using the EA harmala approach. the husks did produce what appeared to be harmala citrate but i decided not to base it and ultimately abandoned it as it appeared at a lower concentration than the seeds produced. The seed extraction was based, filtered and weighed producing .25% of what should be harmine. (Being a small batch, there appeared to be some loss via filtering).

I then conducted a 90g dried seed run (this time washing the red fruit away with a finely grated metal sift (the seeds surfaced was scratched and washed away as well). The idea was to get more dried seeds than fruit in the hope the seeds contained more harmine than the fruit (i was hoping for .5%+). This extraction yielded .25%. Concluding perhaps the fruit contains a bit of harmine (or possible the seeds surface). If it had yielded .5% I would have considered sending it off for lab analysis .

However, I believe the roots still may be worth doing an extraction on, which I hope to do next.

So is Passiflora Caerulea a viable source for harmine? [Edit: NO it is not] I would say possibly if one was desperate and couldn't access B caapi or Syrian Rue. 100g of seeds should get you 1 pharmahusca trip. Whether it is entirely harmine is up for debate without a LC MS test. The EA harmala approach has proven to be very selective with harmine/ harmaline when using Syrian rue and one would assume it should be for passiflora as well.

This however, does leave the door open to other varieties of Passiflora. Or the possibility of selective breeding.

Note: Seeds where harvested in late Summer.
In addition, it would appear the seeds contain double the alkaloids than what the leaf and flowers do (when compared to the study).


Passiflora Incarnata vs Passiflora Caerulea

High speed analysis of harmala alks from passiflora PPM.


Additional information.
In the highspeed analysis study, although PPM don't equate to mg per gram, it does give a good indication of what other varieties maybe viable. Laurifolia L. appear to come out ontop and produced 146 times more (PPM) detection than Passiflora Caerulea for harmine. Meaning it may have a good percentage of harmine in it. However, Laurifolia is a tropical variety.

iu


Edit: It appears another 50mg+ crashed out of the sodium carbonate water. Either it slipped through the filter or took longer to crash. LC MS to follow.
 
I have decided to get a LC MS analysis on the final product, in the hope this sparks interest in other varieties of passiflora.

If the results do come back as relatively pure harmine this could actually be good news. For those who can't access Syrian Rue or B caapi this may be a good interim alternative until something better is found. 400g of seeds (which is harvestable from a medium size bush over spring/ summer) would potentially give 1g of harmine.

But who I think may benefit from this test is those in colder climates Passiflora Caerulea has been known to survive and grow back from 5°F winters (-15°C), other websites state it survives fine down to -10°C (14°F). For those in cold snowy climates with no access to harmala materials this may be worth looking into.
 
Hi nexians,
Some exciting and disappointing news. The exciting news is a LC-MS was carried out by solaris analytical on this extraction, the dissapointing news is it was not favourable or inline with the literature.

The EA harmala approach has been proven to be very selective with rue but not selective as one would of hoped with passiflora.

The LC-MS indicated that the end result pulled contained no harmine but a variety of junk (mainly flavournoids). Basically despite some published articles, passiflora caerulea fruit and seeds did not contain harmine (shame the extraction looked good).

Leaves, flowers and roots still may have potential, but it is looking more doubtful. I was hoping to spark interest in other passiflora varieties and find a few with decent harmine alkaloid percentages.

"Such is science".
 

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The parent ion in several injections was 572 m/z, which corresponds to a luteoline dimer....looking at the luteolin(e) structure (the prominent flavonoid present in passiflora spp.), it's evident where dimerization can occur....there is a carbonyl and hydroxyl on the lower part, which is a hydrogen donor, and acceptor, respectively....a second luteolin can bind those with the double hydroxyls at the far right.


1024px-Luteolin.svg.png
 
Sorry benzyme just revisiting this, I'm not the best at reading the results i believe i have a very basic understanding of the abundance vs molecular weight but I'm not as good at understanding cleaved function groups, dimers etc. I think i understand the dimer at 572, so its basically 2 luteolin molecules combined.

Is there a way to estimate luteolin(e) percentage? Or am I getting this wrong and LCMS results can't accurately gauge this based of too many factors.

I only ask because after a bit of research luteolin appears to be a MAO-I. A fair few flavornoids are, apparently.

So maybe there was some success here?

And maybe luteolines and other flavornoids are responsible for people reporting MAO inhibition with ayahuasca brews, when passiflora is used as an alternative or adjunct?
 
benzyme said:
There was also a constant in all the injections...an oligomer pattern, where the difference between peaks was 68 mass units.
On the face of it, this mass corresponds to a isoprenoid subunit, C5H8 - which is of course ubiquitous in nature. However, when viewed at a higher resolution it seems to be just over 68.6 mass units and this doesn't seem to line up so well: (5×12.011)+(8×1.0079)= 68.118-ish

Could we still be seeing some prenylated derivatives? As an example, bergamottin is a prenylated furanocoumarin with powerful inhibitory effects on CYP3A4. [Just as a 'what if' - perhaps some prenylated luteolin derivative could have a stronger action as a MAOI and some of the variation in efficacy of passionflower preparations might result from this.]

Quite a lot comes up with a search for 'prenylated+flavonoids'.

Any thoughts?
 
Interesting observation and theory DFZ, a bit above my pay grade and knowledge though.

I guess one way to find out if it has MAO inhibitory effects, might be to do a a bioassay with DMT.

Getting dose right might be tricky if it even works.
 
After a bit more research my worry with a bioassay is that passiflora could contain cyanide and cyanogenic glucosides.

The extract results don't seem to contain any cyanide, dhurrin, amygdalin, prunasin, linamarin, lotaustralin, simmondsin or vicianin. And the process would likely eliminate these chemicals/ sugars, I'm tipping.

So it may appear safe to bioassay, there's a wide spectrum of molecules in that sample though.
I looked at the E book and couldn't find any other flavornoids listed in there that matched the lab results so it's unknown what flavornoids or alkaloids where pulled.
 
Just an update attached is the current (but not limited to) compiled list of flavornoids, alkaloids found in P. Caerulea.


According to the literature there is still a chance the leaves contain harmine. And perhaps one of the flavornoids pulled acts as a MAOI as some do, whether its pyschoactive in the way of harmala is another story. In anycase, it is unlikely the fruit and seeds are of much use for harmine alkaloids.


downwardsfromzero said:
benzyme said:
There was also a constant in all the injections...an oligomer pattern, where the difference between peaks was 68 mass units.
On the face of it, this mass corresponds to a isoprenoid subunit, C5H8 - which is of course ubiquitous in nature. However, when viewed at a higher resolution it seems to be just over 68.6 mass units and this doesn't seem to line up so well: (5×12.011)+(8×1.0079)= 68.118-ish

Could we still be seeing some prenylated derivatives? As an example, bergamottin is a prenylated furanocoumarin with powerful inhibitory effects on CYP3A4. [Just as a 'what if' - perhaps some prenylated luteolin derivative could have a stronger action as a MAOI and some of the variation in efficacy of passionflower preparations might result from this.]

Quite a lot comes up with a search for 'prenylated+flavonoids'.

Any thoughts?


Wouldn't the base compound (potentially) be at 229.1 and then something is adding 68 mass units to the others each peak 297.1, 366, 434.4,502.8,571.5?

I might not be fully understanding the results here, DFZ.
 

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