October 3 - Chris Jenks
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Transcript of October 3 - Chris Jenks
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Research on Production of Ibogaine from Voacanga and Iboga
By Christopher Jenks, Ph.D.From Sacramento, California
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Iboga extraction, reviewPowder the barkExtract it with dilute acid (vinegar)Filter out the barkMake the extract basic (ammonia)Filter, dry and powder the TA (Total Alkaloid)
Extract the TA with acetoneFilter out the spent TATitrate the extract with hydrochloric acidFilter and dry the PTA HCl (Purified Total Alkaloid)
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Iboga vs. Voacanga
1 kg Iboga root bark(~3% ibogaine)↓ Extraction
100 g Total Alkaloid (TA)(~40% ibogaine)↓ Precipitation
40 g Purified TA HCl(~80% ibogaine)
1 kg Voacanga bark(~0.35% voacangine)
↓ Extraction115 g Total Alkaloid (VTA)
(~3% voacangine) ↓ Purification ↓ (chromatography?) 3 g Voacangine ↓ Hydrolysis Reaction
Crude ibogaine↓ Purification
2 g Ibogaine HCl
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Advantages/Disadvantages of Voacanga
Advantages Sustainable, takes pressure off iboga Decreasing cost May make ibogaine affordable in poor
countries
Disadvantages Less familiar than iboga derived ibogaine More complicated production requires
central facility
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Ideas to Reduce Costof Voacangine Extraction
● Instead of separating the Voacanga bark, use the whole wood, including the trunk, to save labor.
● Instead of extracting the plant material with organic solvent, use dilute acid (as for iboga).
● Instead of separating the voacangine from the other alkaloids by chromatography, use an extraction process where solvent is recycled.
● Do all this as close to the farm as possible.
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Voacanga Alkaloid Extraction
Extracting Voacanga alkaloid is verymuch like extracting iboga alkaloid.
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VTA (Voacanga Total Alkaloid)
And it produces a similar, solid total alkaloidwhich contains most of the voacangine.
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VTA vs. (iboga) TA
● Iboga TA is useful because it normally contains about 50% of the four main iboga alkaloiods, ibogaine, ibogaline, ibogamine and tabernanthine.
● Voacanga TA (VTA) contains only about 3% voacangine and, unlike TA, seems to be useful only as a stable intermediate on the way to isolating voacangine.
● Since the voacangine is isolated from VTA by extraction of the VTA, there may be no need to isolate VTA as a solid at all.
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What I Wish Had Worked
This would have made purification so easy and cheap,if it had worked. But no ibogaine was detected at the end.
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The Mystery of the High Rf
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Why Voacangine is an Especially Weak Base
In general, a compound which moves higher on the chromatogramis considered less polar, since it interacts less with the polar silica.But voacangine moves higher than the other iboga alkaloids.
Why?
Because it is less basic, due to the ester group.Silica is not only polar – it is also slightly acidic.
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Voacangine Refinement (Step 1)
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Extract VTA with Straight Vinegar
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Filter the VTA Extract
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Extract the Filtrate with Toluene
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By Mixing and Waiting and Draining
(Warning: This and subsequent steps get repeated 3-6 times)
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Wash the Toluene Emulsion with Water
The alkaloids in the water washes are precipitatedwith base and added to the next batch of VTA.
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And Extract the Emulsion with 1% HCl
The toluene emulsion gets reused to extract the VTA vinegar extract again.
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Add Ammonia and … Oops!
Suspended toluene makes PVTA come out as an oil.It looks the same after filtering as before,With little being filtered out.
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Extract the HCl with Petroleum Ether
This removes suspended toluene and clarifies the extract.The petroleum ether can be reused many times and eventually recycled.
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Now the Precipitate Filters Nicely
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The Filtrate is Nice and Clear
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This is How Three Runs Look
Dried PVTA, ~20% voacangineStable intermediate. Spots are:
SV: Spent VTA RV: Recovered VTA W1 – W3: Water washes 1-3 H1 – H3: PVTA from HCl extracts 1-3
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Voacangine Refinement (Step 2)
Voacangine, being weakly basic, has more relative stability inunprotonated form in acetone than the rest of the alkaloids.
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Extract the Dried PVTA with Acetone
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Add HCl and Filter
Unlike with iboga, there is less voacangine inthis alkaloid salt mixture than was in PVTA. It canbe recycled with the next batch of VTA.
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Distill Most of the Acetone
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And Evaporate the Rest
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Until Dry
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Dissolve this up in Water
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And Precipitate with Ammonia
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Filer and Dry to get 86% Voacangine (VRA)
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Shows the Enrichment of PVTA to VRA
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VRA is 86% Voacangine by NMR
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Hydrolysis Requires Hydroxide
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VRA Hydrolysis
Hydrolysis of voacangine by KOH in 50% refluxing isopropanolfor 20 hours gives promising results.
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Decarboxylation Results
Voacangine
Ibogaine
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Another Promising Decarboxylation Method
From: Renner, U.; Prins, D. A. and Stoll, W. G. "[Alkaloids from Conopharyngiadurissima Stapf. Isovoacangine, conopharyngine, conodurine, and conoduramine.]",Helvetica Chimica Acta, (1959), 42(5), 1572-1581 (German)
Translation:Ibogaine from Voacangine - with hydrazine hydrate: 7.36 grams of Voacangine, 40 mL of absolute ethanol and 40 mL of hydrazine hydrate were heated under reflux for 48 hours. The onset of crystallization on cooling was completed by careful addition of water and ice-cooling. After aspirating, 5.13 g ibogaine was collected, mp 144-146. After recrystallization from methanol, the product was pure, mp 149-151.
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Scaling Up...
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Very Complicated Factory Plan
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Very Sophisticated Computerized Controllers
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And Space-Age Sensors!
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All Ready to Go!
● After months of planning...● After buying all anticipated equipment and
chemicals...● After remodeling a house into a laboratory...● After arranging all our lives around this big event...● All we need is the 50 kilograms of Voacanga bark
in the other bag...
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WHAT IS THIS?!THIS BARK IS ROTTEN!!!
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Still Good as Mulch...
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So We Repurposed the Equipmentto Extract Iboga Instead
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A Robot Servo Controller Automates the Pumps
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Using Custom Software
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Though Grinding Root was Still Tedious
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And I Tested What I Could
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And Learned Some Strange Lessons
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For Our Voacanga Factory Someday
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Thank You for Your Attention
Please contact: email: [email protected] facebook: chris.jenks.129 skype: chris_jenks cell: (916) 317-2222