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Do Alkaloids Evaporate in Water? Options
 
Nibs
#1 Posted : 5/16/2020 8:14:25 PM

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My question is specifically relating to harmala alkaloids, but it could be applied to any kind. When boiling plant manterial is it possible for alkaloids to become trapped in water vapor? My initial thoughts are no, because when you do reductions they become more concentrated in the water, also in many traditional ayahuaaca brews they are boiled for hours.

If a brew were to be almost completely boiled off, is it possible that with little water left to be soluable in, could harmalas be evaporated off, or would they convert back to solid form and remain with the plant material?
 

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gogamoga
#2 Posted : 5/16/2020 8:17:41 PM

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Harmalas get evaporated with the steam, but in trace amounts. (Based on my own observation while using soxhlet extractor on rue seeds and UV light)
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Brennendes Wasser
#3 Posted : 5/17/2020 3:52:49 PM

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Normally when performing a steam distillation on plant material you would only get essential oils, and these are called "oils" for the reason of not being an Alkaloid, having no base and therefore not existing as an Ion inside of the material.
Common stuff that can be extracted are Terpenes and these are all either just Hydrocarbons or maybe carry an alcohol or ketone.
Altogether they dont have an ionic form in physiological environment and so they can migrate over when a plant soup is heated at boiling temp.

Quote:
Harmalas get evaporated with the steam, but in trace amounts. (Based on my own observation while using soxhlet extractor on rue seeds and UV light)


But regarding alkaloids, they should not be vaporizing at all, so it wonders me how you saw it with UV light - did you place a UV source behind the vapor and it was slightly glowing? Normally I would just except them to do so in solution. But still then this may be indeed a hint that there would be some in the vapor phase, but normally I would strongly say alkaloids wont ever migrate to the gas phase.

But more precise on your question you are totally good to go to just reduce you soup to whatever amount. You will not loose any amount of the Harmalas - or at least not noticable. Cooking the seeds 2x for 2 h is totally no problem.
But if you want to be super safe, just boil them at 80 - 90 °C.

But regarding concentration:

Why do you even want to concentrate them quite much? Is it for a brew or do you just want to perform a regular Harmala extraction?

In the later case just basify to 11+ and then decant as much water as possible, then filling up with new water and let the Harmalas settle down. Repeat until you have practically clear water above the light tan alkaloids and also a pH of around 7-8. That would be a very easy way to get good Harmalas, the back-salting step to precipitate them as *HCl or *OAc is not even needed and just increases time + decreases yield.
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gogamoga
#4 Posted : 5/17/2020 3:55:41 PM

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The UV glow appeared inside the condenser column above the soxhlet. I was surprised myself. I am pretty sure there was no contamination.
Harmalas sublimate, so maybe this is the reason?
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Mindlusion
#5 Posted : 5/17/2020 11:38:59 PM

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most definitely sounds like sublimation, harmalas are certainly capable of this, especially the less polar harmine
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downwardsfromzero
#6 Posted : 5/18/2020 1:54:06 AM

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Oh, harmala alkaloids - at first I was thinking, "Well, coniine might a little bit, but who would want to be playing around with that?"
(Coniine is the main toxic compound in hemlock, for all you non-phytochem folks out there.)

It's easy to imagine harmine being steam-volatile because it is fully conjugated and thus fairly reminiscent of naphthalene, which is definitely steam-volatile.
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Mindlusion
#7 Posted : 5/18/2020 1:56:32 AM

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downwardsfromzero wrote:


It's easy to imagine harmine being steam-volatile because it is fully conjugated and thus fairly reminiscent of naphthalene, which is definitely steam-volatile.


my thoughts exactly
Expect nothing, Receive everything.
"Experiment and extrapolation is the only means the organic chemists (humans) currrently have - in contrast to "God" (and possibly R. B. Woodward). "
He alone sees truly who sees the Absolute the same in every creature...seeing the same Absolute everywhere, he does not harm himself or others. - The Bhagavad Gita
"The most beautiful thing we can experience, is the mysterious. The source of all true art and science."
 
Nibs
#8 Posted : 5/18/2020 7:19:31 AM

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Brennendes Wasser wrote:
Why do you even want to concentrate them quite much? Is it for a brew or do you just want to perform a regular Harmala extraction?


I've seen people talk about over reducing or nearly completely boiling off their acid baths, and i have come close to doing this myself by mistake. Assuming a reduction wasn't cooked until it was dry and have the harmalas destroyed, i was curious what would happen if they ran out of water to be suspended in. Would they would be completely lost when the broth reached that threshold?
 
 
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