Vasicinone, Vasicine and Deoxyvasicine

[endlessness]

What do we know about them? (this first post will be edited as new information comes in)


Vasicine

XlogP3: 0.4


Vasicinone

XlogP3: 0.4

Deoxyvasicine

XlogP3: 1.0



Phytochemistry:

Appart from the Harmaline and Harmine, Syrian Rue (Peganum harmala) also contains a significant amount of Vasicine and Vasicinone (and Desoxyvasicine/peganine). How much is there in the seeds? Can we find exact numbers?

Pharmacology/Toxicology



These quinazoline compounds are generally considered as "unwanted" alkaloids in rue extractions because they do not show MAOI activity and they are known uterotonic, oxytocic (can facilitate childbirth by increasing uterine contractions) and abortifacient (for examples source 1, 2) therefore specially for pregnant women they should definitely be avoided.

But appart from this uterotonic effects, and for women that are not pregnant and men, are they really unwanted?

Shulgin has said that we should avoid it (his gut feeling, not hard data), but I couldnt find any more negative studies about it. I can see it is a bronchodilator and relaxant (source 1, which might even be interesting in some cases (maybe diminishing the effects of bufotenin's bronchoconstriction ?). What else can we find out about their effects and toxicity? Maybe if someone can find the original of this paper it also helps


Separation

We do know that they can be separated from harmine and harmaline by doing a manske salt precipitation. The sources for this is both burnt (a nexus member) analytical tests with crude manske extracts showing only harmala alkaloids, but also I remember that shulgin had analyzed a salt-precipitated harmala sent by someone that also did not contain the quinazoline compounds, but I cant find the source where I read this, will keep looking for it and post here when I do. Appart from that, another publication describing an extraction of harmalas with a manske step in the middle also failed to show the presence of quinazolines (Phytochemical Studies of the Alkaloids from Peganum Harmala. Applied Chemistry ,Vol. 12, No. I, May 2008, 101-104, attached to this post)


For some reason the hydrochlorides of these substances do not precipitate in a salt saturated solution. Why? What chemical explanation is there for this?. So far this seems to be the only reliable way to make sure they are not present in harmala extractions. Is there any other way? Are they really unwanted?

 

[burnt]

SWIM did not observe them in the salt precipitations. SWIM is not sure how amendable these compounds are to GC however.

However SWIM did do a diethylether extract of a basic salt solution once and observed a range of compounds. If we could get a list of the masses and if available the mass spectra SWIM could compare them with the compounds SWIM observed.

SWIM can post the images later on.

 

[burnt]

Potential detection of vasicine and deoxyvasicine.

Ok so a long time ago in a galaxy not so far away SWIM made a diethylether extract of an aqueous basic solution (pH 9.7) of p harmala after harmaline and harmine precipitation. SWIM was curious what compounds were not precipitating and if more alkaloids could be detected. SWIM analyzed this material by GC-MS.

SWIM is going to make a number of replies with pictures to make this easier to explain. First SWIM shows the general chromatogram with some labels. Harmaline is the major alkaloid with harmine and THH (yes its THH) present in lower amounts. Also a number of unknowns are present which will be discussed below.

 

[burnt]

The first unknown may be deoxyvasicine. Its mass it 172 and there is a 172 peak. The base peak (largest peak) is 171 which would represent M-1 (m being molecular mass). The 143 peak could represent the loss of CH2 and CH3 perhaps from the carbon atoms of the left hand side of the molecule especially if the ionization occurs at either nitrogen. 143 - 129 is 14 which would represent a loss of nitrogen. So yes perhaps this fragmentation pattern makes sense but one should explain more ions to be sure.

 

[burnt]

The second unknown may be vasicine. The mass is 188 and a 188 peak is present. Again the base peak is M-1 187. Again there is a loss of CH2 and CH3. There is also M-16 17 etc which would represent loss of oxygen from the hydroxyl group although this ion is small its there. So again the fragmentation pattern would make sense. But again as with deoxyvasicine this spectra should be compared to a literature report.

 

[mumbles]

A lot of useful lit values in the book The Alkaloids: Chemistry and pharmacology Volume 29 By Arnold Brossi, page 114 onwards. The googlebooks preview is incomplete and I haven't been able to find that particular volume elsewhere. The Alkaloids: Chemistry and Pharmacology

 

[imPsimon]

Bump!

I really cant see any reason to call these "unwanted" chemicals since they seem
to hold very good properties...except if your a pregnant woman.

"It has been used as an antispasmodic, bronchodilator, and mucolytic agent in asthma and other respiratory conditions."
(Justicia adhatoda - Wikipedia)

The plant Adhatoda Justicia (syn, Adhatoda vasica) has been used as a medical plant for a long time in
Asia and it's main working chemicals are vasicine and vasicinone.
I have one myself and it's incredibly hardy, grows enormous leaves in a small pot and
the leaves wont loose color or wilt when left to dry for a bit.
Eventually Orchid-like flowers will pop out as well making it an very nice ornamental.

Review & Future Perspectives of Using Vasicine, and Related
Compounds

http://iglobaljournal.com/wp-content/uploads/2011/02/RACHANA-ET-AL-9.pdf

So how do we separate these chemicals from our "rue" extractions and how do we
extract these chemicals in an easy homebrew way from our adhatoda plants?

Picture of my recently replanted adhatoda. It was the same size in a pot about a quarter the size of the one in the picture

 

[ouro]

I don't think burnt is around anymore... but that is the gcms from *after* extracting the harmalas? meaning that even after removing the majority of the harmalas, there is still a 4x concentration of harmaline compared to the next biggest impurity? It sounds like the concentrations of vascicine etc are extremely low in peganum harmala seeds.

 

[endlessness]

Yeah as I mentioned in my first post, there seems to be some positive aspects to these alkaloids, bronchodilator etc etc. But then there are the problematic aspects if you are a pregnant woman (or maybe a woman in general, the uterotonic effects can be unpleasant?)

In any case, a simple A/B should do the trick in getting these alkaloids out, evene in that plant you have (it should also get any other alkaloids that are present, are there any other?). And to separate from harmine/harmaline in rue, just do a manske, then when the precipitated alkaloids (harmine/harmaline) are filtered, add a base, which should precipitate the vasicine/vasicinone/deoxyvasicine

By the way, im attaching the following publication:

Laakso, Into
(1990) Determination of vasicine and related alkaloids by gas chromatography-mass spectrometry Journal of chromatography. 505 2 p.424-428

 

[imPsimon]

Yeah as I mentioned in my first post, there seems to be some positive aspects to these alkaloids, bronchodilator etc etc. But then there are the problematic aspects if you are a pregnant woman (or maybe a woman in general, the uterotonic effects can be unpleasant?)

In any case, a simple A/B should do the trick in getting these alkaloids out, evene in that plant you have (it should also get any other alkaloids that are present, are there any other?). And to separate from harmine/harmaline in rue, just do a manske, then when the precipitated alkaloids (harmine/harmaline) are filtered, add a base, which should precipitate the vasicine/vasicinone/deoxyvasicine

I'm in the middle of a rue extraction right now and is about to filter out the harmalas with a coffee filter.
You're talking about after I have salted out the harmalas later, correct?

Yesterday I made tea from 2g of dried leaves to treat my very nasty cold and I drank about 1g when when I decided to leave the tea project until I get some more gelcaps since it tasted horrible.
Not your Earl Grey cup of tea.
The amount I ingested really cleared up my lungs and made my breathing easier.
Placebo is a strong effect however so more experimenting is required.

I cant seem to find the active dosage for these compounds, it might be hidden within that
iglobal pdf from my last post but I'm not trained in chemistry so it's a lot
of gibberish to me.

 

[embracethevoid]

Vasicine and its derivatives are found in Peganum Harmala (Syrian Rue) and Adhatoda Vasica (Zeylanica)/Justicia Adhatoda (Acanthaceae)

Review & Future Perspectives of Using Vasicine, and Related Compounds (Jan 2011)

This paper shows that vasicine and derivatives have the following properties:

* Antioxidant and anti-inflammatory activity
* Genoprotectivity (DNA protection)
* Hepatoprotective activity (liver protection)
* Antitussive and bronchodilatory activity
* Muscle stimulant activity (smooth muscle - uterus, trachea)
* Abortifacient activity (pregnant women beware!)
* Anti-diabetic activity
* Anticestodal activity (kills off intestinal parasites)
* Antileishmanial activity (protects against certain protozoa)
* Anti-helminthic activity (kills off parasitic worms)
* Anti-bacterial activity: anti-mycobacterial activity
* Anti-ulcer activity

This is one sweet ass "toxic" chemical methinks! I do believe that in light of this it is clear that the community has assuredly greatly misunderestimated this potent healing agent. Not so sweet for the womb but otherwise absolutely magnificent for the lungs, guts, brain, bloodstream and DNA.

 

[Hyperdimensional Cuttlefish]

I like the feel of the vaporized full spectrum Rue freebase vs the Manske separated freebase IMO. Found the same stuff as you, so no more Manske for me. Only the Gibran tek in the wiki....besides it's dead simple and less potential loss.

 

[jamie]

I really like rue as it is as well. I brew rue tea and it's great. I like manske teks as well but mostly I just work with the tea when I am taking a full dose. I use the manske xtals for sublingual microdoses.

I never found rue toxic.

 

[nen888]

..hey that's great thanks embracethevoid
..to me whole syrian rue has a healing power different to b. caapi..it is more demanding of diet..i really like it for this..
.

 

[InMotion]

Yes, syrian rue is a very powerful, affordable, medicine. I don't mind syrian rue brews, however I prefer alkaloid extractions. Granted the manske is reported to remove a lot of the vasicine.

I have noticed a pink/red precipitation from basifing manske water. Though I don't have much to add, it's hard for me not to make a fan post when it comes to this plant material .

 

[universecannon]

Very interesting, thanks for this info

I've been taking rue or rue harmalas almost daily for the better part of a year and i really love it.. The past month or two i've been adding about half a gram to every fruit smoothie i make..it actually adds a nice element to the flavor, and has been very blissful and interesting

 

[BecometheOther]

I love syrian rue, I always grind up the whole seeds and ingest the whole lot

 

[dondonaldson]

Very interesting, thanks for this info, :thumb_up:

 

[Silly(c)One]

Anyone knows if the effects of the vasicine work when smoked (in changa) ?

Looks like the miracle component from rue...
Makes it look like Ayahuasca...
Any idea if those properties exist in caapi, and from which molecule ?

What makes us purge, both in Caapi and rue ?

 

[SnozzleBerry]

Makes it look like Ayahuasca...

How do you mean?

As far as the purge, probably a combination of harmalas and tannins, as both can cause nausea.