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General interest in Voacanga africana Options
 
entheogenic-gnosis
#1 Posted : 3/22/2016 5:12:34 PM
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I have had a long standing interest in iboga alkaloids, and was particularly interested in Voacanga africana.

(I also have a good deal of the seeds of this plant in my collection, and wanted to consider growing it, though I would have to do this indoor, and really I'm not sure if this is even a viable indoor species, I doubt it is, but am still interested in its cultivation... )


Quote:
Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the rootbark of the Voacanga africana tree, as well as in other plants such as Tabernanthe iboga, Tabernaemontana africana, Trachelospermum jasminoides and Ervatamia yunnanensis.[2][3][4][5] It is an iboga alkaloid which commonly serves as a precursor for the semi-synthesis of ibogaine.[6] It has also been demonstrated in animals to have similar anti-addictive properties to ibogaine itself -Wikipedia


Major alkaloids reported from Voacanga africana stem-bark include: voacamine (7.2%), voacangine (5.6%), voacristine (4.0%), voacorine (3.7%), and vobasine (1.6%) (Thomas & Biemann 1968 ). Percentages are of the total alkaloids present; total crude alkaloid content was 0.2% by weight. Other researchers have found total crude alkaloid contents of stem-bark as high as 3.5% (Janot & Goutarel 1955).

Many of these compounds are similar in structure to ibogaine, and ibogaine is claimed to occur in trace amounts in this plant.

So, if a person dependant on opioids were to take Voacanga africana seeds, would these iboga alkaloids produce adverse effects? Would it produce anti-addictive effects? Or perhaps all the opioid receptor agonism could greatly ease withdrawal symptoms from opioids?




Glick et al., (96) demonstrated that ibogaine and several iboga alkaloids (tabernanthine, R- and S-coronaridine, R- and S- ibogamine, desethylcoronaridine, and harmaline) reduced cocaine self-administration in rats in a dose-related fashion (2.5-80 mg/kg). For some alkaloids, these effects were seen the day after injection. O-Desmethylibogaine (40 mg/kg) (89) and 18-methoxycoronaridine (97) were also reported to inhibit cocaine self-administration.
Ibogaine dose dependently (2.5-40 mg/kg) reduced intravenous morphine self-administration in female Sprague-Dawley rats immediately after injection as well as on the next day (6Cool. In some animals, a reduced morphine intake was observed for several days; other rats required several doses of ibogaine to achieve a prolonged reduction. Similar effects were demonstrated for other ibogaine-like alkaloids including O-desmethylibogaine (89), tabernanthine, R- and S-coronaridine, R- and S- ibogamine, desethylcoronaridine, harmaline (96) and 18-methoxycoronaridine (97). However, data from another study revealed somewhat different results. Thus, Dworkin et al., (109) found that ibogaine (40 or 80 mg/kg) diminished heroin self-administration in male Fisher rats only on the day it was administered. Moreover, the same study revealed that ibogaine treatment resulted in a 97% decrease in responding for a food reinforcement schedule, suggesting that its effects on heroin self-administration were unspecific.
Ibogaine-induced inhibition of morphine self-administration has been found to be reversed by sequential administration of a kappa antagonist (norbinaltorphine, 10 mg/kg) and an NMDA agonist (NMDA, 20 mg/kg). Neither norbinaltorphine nor NMDA alone were effective in this respect (8Cool.
Ibogaine (10-60 mg/kg) reduced alcohol intake in alcohol-preferring Fawn Hooded rats, without affecting either blood alcohol concentrations or food intake (110,111). The authors concluded that a metabolite could be involved, because ibogaine was effective in this measure when administered intraperitoneally and intragastrically, but not subcutaneously (112). A recent study demonstrated an attenuation of alcohol consumption by the ibogaine congener, 18-methoxycoronaridine in rats (113).



Ki-values in μM
Receptor Ibogaine Noribogaine
κ-opioid 2.2 0.61
μ-opioid 2.0 0.68
δ-opioid >10 5.2
NMDA 3.1 15
5-HT2A 16 >100
5-HT2C >10 >10
5-HT3 2.6 >100
σ1 2.5 11
σ2 0.4 19



None of those little yellow faces are supposed to be there, there must have been 8's too close to this " ) "

-eg
 

Good quality Syrian rue (Peganum harmala) for an incredible price!
 
entheogenic-gnosis
#2 Posted : 3/24/2016 11:04:02 AM
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I've read here and there that this plant has potential anti-addictive action similar to ibogaine...

Quote:
Major alkaloids reported from Voacanga africana stem-bark include: voacamine (7.2%), voacangine (5.6%), voacristine (4.0%), voacorine (3.7%), and vobasine (1.6%) (Thomas & Biemann 1968 ). Percentages are of the total alkaloids present; total crude alkaloid content was 0.2% by weight. Other researchers have found total crude alkaloid contents of stem-bark as high as 3.5% (Janot & Goutarel 1955)


Quote:
It [Voacangine] has also been demonstrated in animals to have similar anti-addictive properties to ibogaine itself -Wikipedia ; Voacangine page


I can't find consistent information regarding opioid dependence and this compound, though that's where my interest is...

I have a good deal of voacanga africana seeds, initially I was interested in the conversion of Voacangine to ibogaine (and I still am), though if Voacangine has potential with aiding opioid withdrawal, I may decide to focus a little more on it...

-eg
 
travsha
#3 Posted : 3/24/2016 4:08:48 PM

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It can sometimes be helpful for addiction. Not a magic pill though. I know a friend who microdoses with it daily and it helped her some.
 
entheogenic-gnosis
#4 Posted : 3/25/2016 2:46:41 PM
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I think it's the "magic pill" concept that may actually be very detrimental to the anti-addictive properties of iboga alkaloids, if it was presented as a withdrawal management tool, rather than as an addiction cure, I think it would better serve those seeking this type of help.

There is no "cure" for addiction.

My interest is in withdrawal management.

I've also been looking into harmala alkaloids, as they share structural similarities to iboga alkaloids.

As well as alpha-ethyl-tryptamine:
Quote:
One property has been mentioned more than once in anecdotal reports. It appears to serve well, with short term dosage regimens, as an effective tool in kicking dependency on opiates. In chronic use, there is a rather rapid tolerance built up over four or five days, that allows a dosage escalation to a daily load of a gram or more. There might be some discomfort such as sores in the softer tissues of the mouth, but apparently the withdrawal from heroin is easy and effective. Here is a potential tool in addiction treatment that might warrant closer investigation. Shulgin ; tihkal


I've also read that dextromethorphan May aide in opioid withdrawal as it has very mild agonism at opioid receptors.

Though ibogaine has always been the most promising compound.

voacangine seems promising as well...

I need to do more research here though...

...I just think there may be potential here, initially it regarded synthesis of ibogaine from voacangine, however, if voacangine has similar properties, the voacangine itself may be worthy of investigation.

I randomly obtained a good deal of voacanga africana seeds, and have just begun to research this species, I was interested in attempting to grow it as well, though this may not be a viable option for one reason or another.

I'm really not interested in consuming the seeds, but I'm happy to have them in my collection and am happy to research and learn about another plant tool.

-eg
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Bancopuma
#5 Posted : 11/14/2016 12:42:02 AM

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I shared this in another thread, but it is actually probably more relevant here.

This should be of interest regarding Voacanga africana extraction and ibogaine production, from some of my email exchange with ibogaine expert Dr Chris Jenks.

"In my own studies, acetic acid doesn't remove alkaloids from root bark as fast as dilute HCl does, but I don't know if that matters in extracting alkaloids from solvent. Actually, based on my recent work with Voacanga, I would expect acetic acid to be most likely to leave behind voacangine in the limonene extract because that is the least basic alkaloid. That's not a bad thing since voacangine seems to only cause stomach aches.

You can extract powdered Voacanga bark with a non-polar solvent and remove most of the more basic alkaloids with weak acid like dilute acetic acid, then remove the weak bases like voacangine with a strong acid like HCl. Bob Sisko uses toluene for the initial extraction of root bark, showing that this is feasible. However, on the scale needed to make a difference in the market it would be much more economical to extract the bark with strong dilute acid and recover them by precipitation with base - or make the extract less acidic and extract out voacangine directly. The only other thing I would like to emphasize, although it is covered in the above presentation, is that these extractions need to be repeated to be efficient, just as the extraction of iboga bark with dilute acid is best repeated at least six times."

...so selective use of solvents may produce a cleaner alkaloid profile from the Voacanga.

A link here (which needs updating), but it might be worth contacting Chris about this:

https://www.ibogainealli...ogaine-production-guide/
 
entheogenic-gnosis
#6 Posted : 1/6/2017 5:00:47 PM
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Notes on the related species Voacanga thouarsii:
Quote:

Voacanga thouarsii
In pharmacology indole alkaloids are by far the most important compounds of Voacanga spp., including Voacanga thouarsii. The main alkaloids of the root bark are dimers of the corynanthean-ibogan class dimers, chiefly voacamine, but also voacamidine and voacorine; vobtusine (a dimer of the plumeran-plumeran class) is an important alkaloid from the root bark. In the stem bark, voacamine and congeners predominate, while vobtusine is often also present. Voacangine and voacristine (= voacangarine) are also major constituents. The leaves contain mainly dimeric alkaloids of the corynanthean-ibogan and the plumeran-plumeran classes, but ibogan monomers, including ibogaine and voacangine, are also found. The alkaloid composition of the seeds is similar to other Voacanga species, and consists almost exclusively of the plumeran-class tabersonine (1.6–1.8%). Voacamine, vobtusine and voacangine have hypotensive, cardiotonic and sympatholytic activities. The leaves of specimens from Madagascar were shown to contain the flavonoid-glycosides rutin and kaempferol-3-glucoside. Callus grown in vitro from leaf material containing 0.9% alkaloids produced 0.3% alkaloids (0.2% in the tissue and 0.1% excreted into the medium). Tabersonine was the only alkaloid isolated from the culture; it was not a constituent of the leaves.
The wood is reddish brown, tough and difficult to saw. It does not plane smoothly because of picking up of grain.

Prospects:
Many of the indole alkaloids found in Voacanga thouarsii and related species display very distinct and interesting pharmacological activities. Some of them have potential as candidates for lead compounds in the development of future medicines.
In some regions the extensive harvesting of fruits and the cutting of trees to gather fruits to fulfil the demand for seeds of large pharmaceutical companies are causing rapid disappearance of Voacanga thouarsii from the wild. Domestication and the development of adapted agronomic practices are needed to counteract this development. In the meantime, local authorities should be vigilant in stopping the destructive harvesting to preserve the species for the future

http://www.prota4u.org/p...sp?p=Voacanga+thouarsii


-eg
 
entheogenic-gnosis
#7 Posted : 1/10/2017 5:19:26 PM
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Some remaining interests on this topic:

·Total alkaloid extraction from voacanga africana seeds
·Isolation of voacangine from total alkaloid extracts
·Technical work-ups regarding conversion of voacangine to ibogaine
·Potential ability of voacangine or other alkaloids from V. Africana to aid in opioid withdrawal, functioning in an analogous manner to ibogaine when used for this purpose.
·Nootropic potential of voacangine, voacamine, vobtusine, amataine, akuammidine, tabersonine, coronaridine and vobtusine derived from voacanga africana. The seeds and bark of voacanga africana were long used as a stimulant and as a hunting aid, it is claimed to improve vision, hearing, concentration, endurance, and so on, all of these properties make me feel that perhaps there might be some nootropic potential to voacanga africana seeds and bark and the compounds contained within them.
·Review of bioassays and anecdotes
·Use of voacanga africana seeds as an admixture to ayahuasca

Misc. Related links
https://www.ncbi.nlm.nih.gov/pubmed/9365804
https://www.ncbi.nlm.nih.gov/pubmed/19652504

-eg
 
entheogenic-gnosis
#8 Posted : 1/14/2017 5:27:23 PM
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Quote:
These results further reveal that the Voacanga africana extract has one-hundredth the activity of ibogaine in depressing synaptic responses. Thus, ibogaine and Voacanga africana extract may produce their central effects by altering dopaminergic and glutamatergic processes.https://www.ncbi.nlm.nih.gov/pubmed/9365804


Quote:
Abstract
Ibogaine is a natural alkaloid of Voacanga africana that is effective in the treatment of withdrawal symptoms and craving in drug addicts. As the synaptic and cellular basis of ibogaine's actions are not well understood, this study tested the hypothesis that ibogaine and Voacanga africana extract modulate neuronal excitability and synaptic transmission in the parabrachial nucleus using the nystatin perforated patch-recording technique. Ibogaine and Voacanga africana extract dose dependently, reversibly, and consistently attenuate evoked excitatory synaptic currents recorded in parabrachial neurons. The ED50 of ibogaine's effect is 5 microM, while that of Voacanga africana extract is 170 micrograms/ml. At higher concentrations, ibogaine and Voacanga africana extract induce inward currents or depolarization that are accompanied by increases in evoked and spontaneous firing rate. The depolarization or inward current is also accompanied by an increase in input resistance and reverses polarity around 0 mV. The depolarization and synaptic depression were blocked by the dopamine receptor antagonist haloperidol. These results indicate that ibogaine and Voacanga africana extract 1) depolarize parabrachial neurons with increased excitability and firing rate; 2) depress non-NMDA receptor-mediated fast synaptic transmission; 3) involve dopamine receptor activation in their actions. These results further reveal that the Voacanga africana extract has one-hundredth the activity of ibogaine in depressing synaptic responses. Thus, ibogaine and Voacanga africana extract may produce their central effects by altering dopaminergic and glutamatergic processes
https://www.ncbi.nlm.nih.gov/pubmed/9365804


-eg
 
entheogenic-gnosis
#9 Posted : 1/15/2017 6:18:52 PM
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216g voacanga africana seed.
(I apologize that the picture appears upside down)

-eg
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entheogenic-gnosis
#10 Posted : 1/18/2017 3:03:05 PM
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Quote:
Chris Jenks, Ph.D., recently self-published a guide to the semi-synthetic production of ibogaine hydrochloride via voacangine extracted from the Voacanaga africana tree. This document improves on previous Voacanga ibogaine production methods by reducing the cost, level of technology and amount of training required and improving the scalability and environmental friendliness of the process.

There are four documents, each outlining a phases of the extraction process.

Phase 1: Isolation of Total Alkaloids http://www.puzzlepiece.o...tion_manual_phase_1.pdf

Phase 2: Separation of voacangine from more basic alkaloids http://www.puzzlepiece.o...tion_manual_phase_2.pdf

Phase 3: Final purification of voacangine http://www.puzzlepiece.o...tion_manual_phase_3.pdf

Phase 4: Production and Purification of Ibogaine http://www.puzzlepiece.o...tion_manual_phase_4.pdf

https://www.ibogainealli...gaine-production-guide/


I see the above information as a fairly good find, I'm beginning extraction and conversion projects as well as bioassay projects involving the plant matter as well as extracts. I prefer to review everything I can before I begin, and am nearly finished compiling information.

Again, these are my main concerns:

Quote:
·Total alkaloid extraction from voacanga africana seeds
·Isolation of voacangine from total alkaloid extracts
·Technical work-ups regarding conversion of voacangine to ibogaine
·Potential ability of voacangine or other alkaloids from V. Africana to aid in opioid withdrawal, functioning in an analogous manner to ibogaine when used for this purpose.
·Nootropic potential of voacangine, voacamine, vobtusine, amataine, akuammidine, tabersonine, coronaridine and vobtusine derived from voacanga africana. The seeds and bark of voacanga africana were long used as a stimulant and as a hunting aid, it is claimed to improve vision, hearing, concentration, endurance, and so on, all of these properties make me feel that perhaps there might be some nootropic potential to voacanga africana seeds and bark and the compounds contained within them.
·Review of bioassays and anecdotes
·Use of voacanga africana seeds as an admixture to ayahuasca

-eg


Any anecdotes, advice, research, comments, etc...would be appreciated.

-eg
 
RhythmSpring
#11 Posted : 1/18/2017 3:07:25 PM

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e-g, I believe there are a few ibogaine treatment centers out there that boast the use of ibogaine HCl made from Voacanga. Have you tried seeking them out and asking them for information?
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pinkoyd
#12 Posted : 1/24/2017 5:31:42 AM

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Cultivation of Voacanga as an indoor plant is entirely feasible. A friend of mine has maintained one for years in his apartment in San Francisco. Last I saw, it was about three feet tall in a two gallon pot. A dwarf compared to mine that are in the ground, but it seems to be a fairly hardy and adaptable plant.
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dreamer042
#13 Posted : 1/24/2017 3:52:03 PM

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entheogenic-gnosis wrote:
Any anecdotes, advice, research, comments, etc...would be appreciated.

I had a kilo of root bark at one point. I tried a few different extraction procedures and ended up with a pretty decent yield (2% ish iirc) of both fumarates and freebase. I never had the courage to bioassay the extracts, nor was I able to talk any of my labrats into it. The whole "this may be the best drug you've ever tried, or it may kill you, you should smoalk it" pitch didn't exactly instill confidence. Laughing

I did work with small doses (a gram or two) of the root bark and found it very stimulating and electric, similar to the LSD onset, quite long lasting as well. I never pushed it higher than very low doses due to other reports of it causing disconcerting heart/bloodpressure issues.

I think I still have a couple hundred grams kicking around. I'd been waiting for a good conversion tek, but last I checked it was still a bit outside the realm of the average kitchen chemist to perform the voacangine->ibogaine conversion. Perhaps I'll try fiddling around with it again at some point.
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Aum_Shanti
#14 Posted : 2/3/2017 9:59:36 AM
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Frome the article mentioned above by entheogenic-gnosis:
Quote:
Ibogaine is a natural alkaloid of Voacanga africana


??? I thought there is no Ibogaine in Voacanga, except maybe in trace amounts ???

What would be the advantage of growing Voacanga instead of Iboga?
I mean the total yield is much smaller, if you want to get Ibogaine in the end. And the extraction and conversion is much much more complex.
Does Voacanga grow faster or is less problematic to grow?

As far as I understood it, the idea of the conversion is mainly to get the pressure off from the natural Iboga plants.

@dreamer.
AFAIK the conversion voacangine to Ibogaine isn't that difficult, but to get the separated voacangine is the hard part. Basically to get rid of all the other alkaloids.
Those who do it commercially do this with a column.
I claim not that this is the truth. As this is just what got manifested into my mind at the current position in time on this physical plane. So please feel not offended by anything I say.
 
entheogenic-gnosis
#15 Posted : 2/3/2017 3:43:24 PM
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Aum_Shanti wrote:
Frome the article mentioned above by entheogenic-gnosis:
Quote:
Ibogaine is a natural alkaloid of Voacanga africana


??? I thought there is no Ibogaine in Voacanga, except maybe in trace amounts ???

What would be the advantage of growing Voacanga instead of Iboga?
I mean the total yield is much smaller, if you want to get Ibogaine in the end. And the extraction and conversion is much much more complex.
Does Voacanga grow faster or is less problematic to grow?

As far as I understood it, the idea of the conversion is mainly to get the pressure off from the natural Iboga plants.

@dreamer.
AFAIK the conversion voacangine to Ibogaine isn't that difficult, but to get the separated voacangine is the hard part. Basically to get rid of all the other alkaloids.
Those who do it commercially do this with a column.


My understanding is that ibogaine is not present in any significant quantity.

As far as the reasoning behind modern interest in converting similar alkaloids into ibogaine, I feel the excerpt from TIHKAL helps explain the situation:

Quote:
SYNTHESIS : There have been three total syntheses of ibogaine reported in the chemical literature. The first of these was a thirteen step process published about 30 years ago. The chemistry lab can serve a fine function for both isolation and purification of ibogaine from plant sources, but in the real world, there is no practical way to start from a bottle of nicotinic acid and actually prepare useful amounts. The parent ring system contains two chiral centers, neither of which is amenable to easy manipulation. Because of these two separate and largely inaccessible chiral centers there are, in theory, four distinct isomers of ibogaine which are difficult to resolve. When the term "synthetic" is used in regard to ibogaine in the scientific journals, it usually applies to the resynthesis of the parent alkaloid from the demethylated metabolite. For reference purposes, here are the finger print number from the infrared spectra: For the free base: IR (in cm-1): 741, 799, 830, 1037, 1111, 1148; mp 152-153 °C. For the hydrochloride salt: IR (in cm-1): 638, 810, 832, 925, 1031, 1149; mp 299-300 °C (dec). -shulgin/TIHKAL


-eg
 
Aum_Shanti
#16 Posted : 2/3/2017 3:53:43 PM
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Quote:
As far as the reasoning behind modern interest in converting similar alkaloids into ibogaine, I feel the excerpt from TIHKAL helps explain the situation:


Yes, this I know. But I personally e.g. cannot understand when people start growing Voacanga to get Ibogaine in the end. If I would grow something, I would grow Iboga.
Or is it much easier to grow Voacanga, or does it grow much faster?
I claim not that this is the truth. As this is just what got manifested into my mind at the current position in time on this physical plane. So please feel not offended by anything I say.
 
entheogenic-gnosis
#17 Posted : 2/3/2017 3:58:31 PM
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dreamer042 wrote:
entheogenic-gnosis wrote:
Any anecdotes, advice, research, comments, etc...would be appreciated.

I had a kilo of root bark at one point. I tried a few different extraction procedures and ended up with a pretty decent yield (2% ish iirc) of both fumarates and freebase. I never had the courage to bioassay the extracts, nor was I able to talk any of my labrats into it. The whole "this may be the best drug you've ever tried, or it may kill you, you should smoalk it" pitch didn't exactly instill confidence. Laughing

I did work with small doses (a gram or two) of the root bark and found it very stimulating and electric, similar to the LSD onset, quite long lasting as well. I never pushed it higher than very low doses due to other reports of it causing disconcerting heart/bloodpressure issues.

I think I still have a couple hundred grams kicking around. I'd been waiting for a good conversion tek, but last I checked it was still a bit outside the realm of the average kitchen chemist to perform the voacangine->ibogaine conversion. Perhaps I'll try fiddling around with it again at some point.


Thank you for the information, it is much appreciated.

Good information in this area is hard to come by.

As far as chemistry goes, I think I'm well prepared, and while I'm still gathering information (any pointers or tips appreciated) my informational aspirations on this topic have shifted more towards general research and experiential phenomena.

I've also heard of voacanga seeds being used as an ayahuasca admixture, but again, I have found very little useful information in this area.

I got sidetracked with some projects involving phenethylamines and have neglected my interests on this topic since, however as I wrap up higher priority research I will be able to resume work here, until then, I apologize if I seem slow to respond or disorganized when it comes to this particular thread.

-eg
 
entheogenic-gnosis
#18 Posted : 2/3/2017 4:02:15 PM
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Aum_Shanti wrote:
Quote:
As far as the reasoning behind modern interest in converting similar alkaloids into ibogaine, I feel the excerpt from TIHKAL helps explain the situation:


Yes, this I know. But I personally e.g. cannot understand when people start growing Voacanga to get Ibogaine in the end. If I would grow something, I would grow Iboga.
Or is it much easier to grow Voacanga, or does it grow much faster?


I can't comment on cultivation as I have never grown voacanga or iboga.

I'm guessing for most legal issues would be a motivating factor.

...though, other than that, I'm really not sure.

-eg
 
 
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