02-09-03 07:07
No 405958
Hello!
I was just wondering if the tryptamines in plants(especially Phalaris) are in their freebase form or in their salt form. I guess that depends on the pH of the citoplasm and the pKa of DMT/5MeODMT.
I had quite some succsess with the extraction of THC witl butane and was wondering if it would work with Phalaris.
Another question is about salvinorin - is it soluble in butane ?
(Hive Bee)
02-09-03 07:16
No 405959
Theoretically, alkaloids will be present in a watery solution which means in their salt form. But dissolved salts become ionic (table salt in water breaks up in Na+ and Cl- ions). But as I said this is the theory. I have no idea if some plant alkaloids are present in not watery tissues. Perhaps there are some weird natural freebases.
But at the moment you extract the alkaloids in a very low pH they will be in their ionic forms.
SVA is very poorly soluble in butane (AFAIK).
bibliopharmacophile
(Moderator)
02-09-03 09:24
No 405978
The plant cytosole is slightly acidic, something like pH 5.5 (?), so the tryptamines are protonated. But they do not form a (homogenous) salt. The counterions are a complex mixture of all deprotonated acids inside the cell.
(Hive Bee)
02-09-03 16:04
No 406078
So, does this mean that if one soaked some dried plant material, properly ground, in a non-polar solvent, that the weak nature of the acidification would release the alkaloids?
SWIM thinks it needs a bit of a base kick to get it fully out, so he is trying out using turpentine and ~pH 12 water together to get the alkaloids out of a plant. However, an experiment he did previously, pre-extracting the plant material with ethanol, then dissolving the extract into a solution with one part demineralised water and the other part naptha, orange went into the water, green stuff went into the np, the orange had nothing in it, but there was mild activity in the stuff taken out of the np fraction. does this disagree with what you have said? It is possible that SWIM didn't treat the h2o part properly though. Further experiments need to be done at some point. Me and SWIM are intent on finding the most effective and OTC methods of extraction that take the least time and result in the cleanest possible alkaloids. A/B works, but other things may work too. A/B makes messy large volumes of aqueous extracts which are hard to work with and don't yield their goodies as quickly as other chemistry experiment results that SWIM has seen, so having successfully A/B'ed meth from rp/i/e reaction, but not from plants, he wants to see if there is better ways that aren't so goddamn messy.
I know naaaathing.
(Hive Bee)
02-09-03 16:26
No 406084
I don't know if this applies to DMT in phalarys, but I know that in most plants the alcaloids are in the state of salts, N-protonated, and the anion comes from tannines. There are two kinds of tannines, the hydrolizables and the not hydrolizable ones. The tannines are phenolic compounds. The hydrolizable ones are di-galloil-esthers of glucose and in hot water they release gallic acid. The non hydrolizable ones are polimers made of glucose and catechine. One of the phenolic H+ protonates the aminic N. Tannines can be eliminated as their Ca++ insoluble salts adding CaCO3 during the extraction. I know this is the procedure for caffeine, atropine and opium. For DMT I don't know.
(Moderator)
02-10-03 04:30
No 406177
My god, it doesn't matter in which state they are in the plant or what counterions they have there. It's just a STATE and it's the extractor's job to modify that state by adjusting the pH.
(Hive Bee)
02-10-03 04:54
No 406180
Yes, this is why I thought an acid/base extraction was necsarry to get the alkaloids from plant matter.
(Moderator)
02-10-03 06:46
No 406197
You probably can't extract protonated tryptamines and Salvinorin with butane. Even tryptamine bases will have a very poor solubility in butane.
(Hive Bee)
02-25-03 20:44
No 411790
So if calcium carbonate is added to the simple water extract of a plant, the tannin drops out. That would leave the alkaloids as freebase right?
In the case of acacia alkaloids, one primary advantage of making the pH to (the figure I think is good for eliminating gak) 4, is not to 'bring the alkaloids into salt', rather it is to alter the pH of the liquid so that less gak dissolves in the water and thus reducing gak in the base part of the extraction. Would calcium carbonate also alter the pH upwards? One of the things about basifying the acid extracts of acacia is at over pH 12 a lot of gak precipitates. This is using sodium. Would potassium work better? Ammonia? If calcium carbonate causes tannins to precipitate would that be more effective than the normal procedures with respect to likewise causing other undesirables (sugars mainly) to stay out of the nonpolar fraction. Is there a way to make sugars precipitate?
Where does calcium carbonate come from OTC? Does making the solution acidic induce the exchange of the alkaloids from tannates to acetates (or citrates/hydrochlorides, depending on the acid used)? What induces such ion transfers? Is there a way to determine whether this is happening (stochimetrically)?
a lot of questions huh.
I know naaaathing.
(Chief Bee)
02-26-03 16:42
No 412096
Where does calcium carbonate come from OTC?
Chalk.
(Moderator)
02-27-03 10:36
No 412328
Isn' that gypsum?
(Chief Bee)
02-27-03 15:25
No 412393
No, Gypsum is hydrated Calcium Sulfate (the anhydrous form is commonly known as Plaster of Paris).
(Moderator)
02-27-03 16:38
No 412409
Blackboard chalk is gypsum afaik. The common name for calcium carbonate is lime or limestone
(Chief Bee)
02-27-03 16:56
No 412414
See http://webexhibits.org/pigments/indiv/ov
(Moderator)
02-28-03 00:35
No 412501
Let's continue at the Couch
