Voacangine fumerate

[JAi]

I've been running a few ideas through my head before I consider experimentation.

One hypothetical question I have is when extracting V. africana, T. sananho and other plants containing iboga like alkaloids, would it be possible to get them into fumerate form in the same way DMT is known to?

Also does anyone know if d-limonene will enrich Voacangine in the same way toluene would? Why or why not?

 

[dreamer042]

I extracted a few hundred grams of Voacanga using limonine at one point, salted out to fumerate salt. Worked fine, beautiful yellow tinged crystals. I also converted a bunch of it to freebase.

My labrats and myself never had the courage to bioassay the final product and I'd advise being especially careful with this extract, there is a reason it's traditionally been used as arrow poison. Don't take large doses of Voacanga, it's not like Iboga.

Be safe :thumb_up:

 

[JAi]

Music to my meta ears dreamer042! It's just good hypothetical information, as it may be then converted to de-ester-ficatable form, perhaps after TLC identification. Are you aware of any thread on iboga type alkaloid TLC?

Honestly I think toluene would be the safer move. This is all just hypothetical

 

[pinkoyd]

it's not like Iboga.

So what IS it like? Inquiring pinkoyds want to know...

 

[dreamer042]

it's not like Iboga.

So what IS it like? Inquiring pinkoyds want to know...

I haven't yet taken the opportunity to dance with old man Iboga, so I can't make any first hand comparisons.

In the doses I've taken Voacanga rootbark (ranging from a couple hundred mg to couple grams) it was very similar to what people report with low dose Iboga. Powerful stimulant, very "electric" feeling, very energetic. It's a lot like maca root to the nth degree. Definitely a stamina medicine, one can easily see why it is used for hunting.

Several accounts I've read with larger doses (3-5-10 grams+), both with the rootbark and with the seeds, reported extremely disconcerting cardiac effects (chest pain, dangerously elevated heart rate and blood pressure, numb extremities) and overall unpleasant experiences with little to no psychedelic effect. Needless to say, the descriptions turned me off the idea of exploring this material at higher doses and/or bioassaying extracts. I'm still sooper curious what the effects of vaping the freebase would be, but that's one for labrats with moar gall than myself

 

[JAi]

it's not like Iboga.

So what IS it like? Inquiring pinkoyds want to know...

I haven't yet taken the opportunity to dance with old man Iboga, so I can't make any first hand comparisons.

In the doses I've taken Voacanga rootbark (ranging from a couple hundred mg to couple grams) it was very similar to what people report with low dose Iboga. Powerful stimulant, very "electric" feeling, very energetic. It's a lot like maca root to the nth degree. Definitely a stamina medicine, one can easily see why it is used for hunting.

Several accounts I've read with larger doses (3-5-10 grams+), both with the rootbark and with the seeds, reported extremely disconcerting cardiac effects (chest pain, dangerously elevated heart rate and blood pressure, numb extremities) and overall unpleasant experiences with little to no psychedelic effect. Needless to say, the descriptions turned me off the idea of exploring this material at higher doses and/or bioassaying extracts. I'm still sooper curious what the effects of vaping the freebase would be, but that's one for labrats with moar gall than myself

Maybe don't on the lab rats, as you said it's life or death kind of disconcerting, one of the alkaloids in there is responsible for these effects, as well as the combination of other dimer alkaloids. I wrote out a whole long post about how to separate the various components from this place, as well as tabernamontana sananho which has less different alkaloids, which are all present in V. africana, unfortunately the side document failed to recover as well as the post I was editing when my battery died.

It all just had to do with the relative pKa of each alkaloid, which I learned are possibly more than most single articles mention -so I put a list off all that I found in order by pKa and added Ibogaine and DMT for reference. Ive really gotta draw it all up again, the point is it's fairly simple to separate the Voacangine and also end up with other guinea pig alkaloids, the important thing is TLC and chromatography to begin identifying what may be in a sample. Some people only want Voacangine so they can remove the ester group and turn it into ibogaine. I have to wonder what two other of the alkaloids in the V.africana would be like without the ester group, and if these are also found in other plants in their 'de-estered' form.

 

[dreamer042]

I would incredibly interested in the information on separation via pka, even if just a simple base to this ph to precip this alkaloid , then base to this ph for this one, and this ph for this one, and so on.

I've been hoping for some time that someone would pop up with info that would move us closer to a kitchen chemist level separation and conversion tek. :thumb_up:

 

[downwardsfromzero]

Looking at the efforts over on the harmala precipitation thread, we'd be looking at overlapping curves. Thus separate fractions would require reprecipitating, most probably.

There comes a point where chromatography might seem a better approach for cost, time and effort.

 

[JAi]

I would incredibly interested in the information on separation via pka, even if just a simple base to this ph to precip this alkaloid , then base to this ph for this one, and this ph for this one, and so on.

I've been hoping for some time that someone would pop up with info that would move us closer to a kitchen chemist level separation and conversion tek. :thumb_up:

Yes, I can do that again soon. Essentially you'll be seeing a straight to toluene from vinigar technique, though the original extract process I read uses HCl and extracts THAT HCl extract with vinegar because he says the vinegar won't extract enough alkaloids on its own - this statement has likely not been put to the test and may be effected by heat and exposure times. Due to lack of experimentation (and chromatography comparison) I don't know if limonene will enrich Voacangine the same way toluene does.

I was considering a parallel extraction to compare TLC results (toluene vs limonene). If I were to do both of the extractions with only vinegar as the starting acid and got nothing or very little, it would confirm that it was a wasted route of extraction to start from vinegar, and the plant material could still be extracted with HCL from there, and parallel extractions carried out again, probably a good recovery step anyway, especially after removing the 'enriched' (or not so in this second recovery parallel extraction) and basifying to pull the additional Guinea pig alkaloids.

Thermosensitivity and Voagangine

Antimicrobial activity of extracted mesocarp of V africana
Anti Ulcer Activity

Chinese study showing 8 alkaloids with chromatography
RESULTS: Eight alkaloids were isolated and their structures were elucidated as voacangine(1), voacangine hydroxyindolenine(2), 19R-epi-voacristine(3), epi-ibogaine(4), vobasine(5), 19-epi-heyneanine(6), vobtusine(7) and voacamine(8 ).

CONCLUSION: Compounds 2-4 and 6 are isolated from this plant for the first time.

An article on V africana extract dated 59 years to the day of this repost edit note this shows 10 alkaloids and that there is a blue UV response.

Here are 2 new alkaloids extracted via cell suspension cultures

Suggests some genotypes of V africana produce mostly tabersonine

aspidosperma-type bisindole alkaloids 1–4 were isolated from the seeds and root bark of Voacanga africana This one reminds me of the macro molecules I've seen elsewhere on the nexus.

11 Alkaloids mentioned The major alkaloids include voacamine, voacangine, vobasine, and ibogaime. Others include voacristine, voacamidine, voacarine, voaphylline, vobtusine, voalfolidine and tabersonine.

 

[JAi]

Of the above searches for bioactive constituents there are a few alkaloids that may or may not be present in the simple extraction process SWIMmers might to do. These are the 2 new alkaloids extracted via cell suspension cultures, "Compounds 2-4 and 6 isolated using a specific chromatography method, I didn't see the whole article, the method to extract aspidosperma-type bisindole alkaloids is unknown to me as well, maybe a cold extraction on fresh material.

This leaves 5 of the 8 here to look at for the time being, until something questionable comes up on a TLC test. Of which the 1958 paper adds voacaminine, voncorine (probably same as voacaline), voacamidine,* voacristine1 and voacangarine, Voacafrine and Voacafricine.

Making the list, see next post for edited version:
voacangine
{19R-epi-voacristine (same as voacristine? )}
vobasine
vobtusine (extracted in week base partition in 1958 )
voacamine (same as ~oacanginine~) (extracted in week base partition in 1958 )
+
voacaminine
voncorine (probably same as voacaline)
voacangarine
Voacafrine
Voacafricine
+
ibogaine
voacamidine
voacarine
voaphylline
voalfolidine
tabersonine
+
alkaloids not being considered at this time
+ I'll add
Heyaneane
Coronaridine
3-HO-Coronaridine



This article below, which I've added more to the list from, suggests some of these other alkaloids may be in the minority:
11 Alkaloids mentioned The major alkaloids include voacamine, voacangine, vobasine, and ibogaime. Others include voacristine, voacamidine, voacarine, voaphylline, vobtusine, voalfolidine and tabersonine.

An article on V africana extract dated 59 years to the day of this repost edit note this shows 10 alkaloids and that there is a blue UV response.

This is very interesting, it has isolation methods included, and we have to wonder what has changed in 59 years, are the names of these molecules even all the same?

 

[JAi]

pKa

+ I'll add these three for reference as well, as some iboga relatives contain them
9.3 Heyneanine
also note 8.68 DMT as we are all familiar
8.05 ibogaine
7.89 Coronaridine


7.4 (40% aq methanol); 5.73 (33% DMF) voacamine (same as voacanginine~)
6.95 vobtusine (extracted in week base partition in 1958 )
6.4 voacorine (probably same as voacaline)
5.9 tabersonine - precursor to other medical drugs
5.77 voacangine (also reported 5.6)
Nexus quotes broken Merck link showing voagangine with voacamine's pka, confusing... pKa: 7.4 (40% aq methanol); 5.73 (33% DMF) (Merck Index)

Also not voacangine is bonded with voacamine, though acid may break the bond. "Cleaved by acid catalysis to voacangine." Would anyone know if acetic acid would be enough to break this bond, and at what strength?





+
alkaloids not being considered at this time, including 3-HO-Coronaridine and others which I have not yet found pka info on: voaphylline, voalfolidine, vobasine, and the 50's compounds:
Voacafrine (50's compound never again mentioned as far as I know)
Voacafricine (50's compound as above)
voacamidine (isomer of voacamine)(extracted in week base partition in 1958 )

Also 6.06 19-Epi-Voacristine Hydroxyindolenine {if that's even the same?)
and voacangarine/Voacristine (possibly different than above) - you'll see why it's probably not important based on what should happen at that pka.
note {19R-epi-voacristine (same as voacristine? )}





Vinposetine (obtained from tabersonine) is also mentioned on the interwebs. This looks like a nootropic alkaloid.

Tabersonine pka ref
google book pka ref

Voacamine and Voacorine pka ref 1964
voacorine and vobtusine pka ref
Voacanine pka
Voacristine
Coronaridine pka ref
Heyneanine

As we know from the Nexus Wiki: The pKa is equal to the same number as the pH when 50% of the alkaloid is in salt form and 50% is freebased. The pH and pKa at which this occurs for DMT is 8.68. Also

9.67 - 5-HO-DMT (bufotenine)
9.3 - 5-MeO-DMT
8.68 - DMT
8.47 - 4-HO-DMT (psilocin)

I found this on Voacangine Biological activity from Dr Duke

So using vinegar it may be possible to get the voacangine and many other alkaloids into solution, more if HCl is used, though I'm thinking less could be more in this situation. Once in solution most of these will not go into a non polar solvent until a base is added, except we know Voacangine will, and that's how we enrich the solvent with Voacangine. This may have something to do with xlogp values if anyone wants to add those to the list that would be an awesome time saver. We pretty much know this has worked for someone already, now how can we tweek the process. I'm thinking it's possible to percolate hot vinegar after letting the root bark sit in vinegar for quite a while, then putting the solvent right on there, and getting Voacangine fumerate. The solvent can also be recycled. From there more alkaloids can be separated by basifying and using the spent solvent again for new alkaloids, though any fumerate salting of this part is getting into questionable territory. I could see trying it with limonene while opting to dry up the toluene. It may be possible to re extract the dried spent root bark with a stronger acid afterwards if there is low to no yield from the acetic acid extract.

 

[JAi]

So I believe what will happen with a solution obtained from acetic acid 'reflux' in a percolator (after soaking plant material a while first, and running it another time or two with new dilute acid and water) is that due to the pka of alkaloids now in the acidic water (which would ideally be concentrated to lower volume) these alkaloids;

6.95 vobtusine (extracted in week base partition in 1958 ),
6.4 voacorine (probably same as voacaline),
5.9 tabersonine - precursor to other medical drugs, though itself is likely responsible for toxic effects (major abundance in the seeds), and
5.77 voacangine (also reported 5.6) (likely the most abundant in root bark)

may actually come across into an added non-polar layer of toluene or d-limonene when added, without any basification step being done.

Therefore when a basification step is done after enriching the solvent with voacangine (possibly mostly), other alkaloids can be separated in a new fraction which will also get a TLC test. This fraction removed by basification would theoretically also include the things on the list with higher pKa.

Even in the paper from 59 years ago the author reports 2 similar fractions, as you can read in the paper.

After TLC, steps can be taken using solvents that would dissolve various components but not others.

I'm about ready to begin experimentation, because it's so easy, not that I have the time to do it just yet, materials yes. I'm open to any potential input before I go through it and post results.

 

[Kash]

Sounds really interesting... did anything ever come of this JAi?

 

[JAi]

Sounds really interesting... did anything ever come of this JAi?

Hey,

I haven't had the time or space but I'll get around to it eventually.