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apothecary

LSA Extraction

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davies_illus1.gif

looks pretty water soluble to me.

quote:


The effects of humic substances on the solubility and mobility of organic contaminants have been the subject of numerous studies. The apparent aqueous solubility of chlordane, DDT, PCBs and chlorodioxins has been observed to increase in the presence of humic substances (Chiou et al., 1987; Johnson-Logan et al., 1992; Webster et al., 1986). This is because the binding of a particular PAH compound by humic substances depends not only on the hydrophobicity of the PAH solute but also on the size of the solute molecule and its ability to fit into hydrophobic cavities in humic substances. An increase in pH and ionic strength was found to decrease the binding of PAHs by humic substances (Schlautman and Morgan, 1993). Hydrophobic organic contaminants (PAHs, benzene, carbon tetrachloride and DDT) can also be adsorbed by dissolved humic substances (Carter and Suffet, 1982; Gauthler et al., 1987; Herbert et al., 1993; McCarthy and Jimenez; 1985; Rutherford et al., 1992). The corresponding Koc values was also found to be strongly correlated with the degree of aromaticity in the humic substances (Gauthler et al., 1987). The mobility of PAHs, PCBs, and chlordane in groundwater systems was observed to have increased in the presence of humic substances (Backhus and Gschwend, 1990; Dunnivant et al., 1992; Johnson et al., 1993; Johnson-Logan et al., 1992). Backhus and Gschwend (1990), concluded that the presence of humic substances (

its not about extracting from plants but shows that in the presence of humic acid organic compounds bind to it depending on particle size. also says aromatic organic compounds bind more readily.

http://www.bioremediationgroup.org/BioRefe...s/HumicAcid.htm

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teonanacatl:

looks pretty water soluble to me.

thats because that isnt humic acid, its simply one of the hundreds of proposed structures for a tiny fragment of humic acids total structure... heres another (at the bottom of the page)... hypothetical segment of the structure of humic acid

Humic acid is insoluable in acidic solutions and virtually insoluable in neutral solutions.

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ahha now thats why it has a good cation exchange capicity. and your right that doesnt look very water soluble.

so let me get this right you perculate acidic water through plant matter then through a collum containing the cation catcher which catches all the goodies, then u dump water and keep resin, basify and there you go.

so if using humic acid couldnt you just make the water acidic so it becomes water soluble and perculate it around with the water, then basify untill the humic acid drops out carrying the goodies with it, seperate layers then basify more so base drops out???

i also did a diagram of what i think would happen when you add some humic acid and mecaline together in acidic water lol (im doin first year chem/biochem so its probably not correct but its good practise to try and do things)

Untitled-1.jpg

you can see the mescaline ion down the bottom left doing its thing with the ionised carboxyl group. the other places i added mesc need to be turned around O- to NH3+. is that what would happen ???

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The alkaloidal extract would have to be acidic to make the alkaloids available, but past a certain point acidic solutions will strip humic acid/humates of all the salts... so a alkaloid probably wouldnt bind to humic acid in 0.1 M HCl... even acetic acid Might be too strong (I dont remember- lol) but I just did a quickie test run with boric acid and borate- sodium tetraborate will react with free humic acid to form a sodium humate solution, and addition of boric acid solution to a solution of ammonium humate (freshly prepared from solid ammonium humate) did not precipitate out humic acid... so in theory if your alkaloid was in aqueous solution as the borate and humic acid was added it might result in the humate of your alkaloid... if the alkaloid humate was Insoluable in water you could filter out the product, baseify, extract with naphtha, and obtain your alkaloid... if your plant extract had say two alkaloids, one of which was unreactive to humic acid or produces a water soluable humate you could make a simple process to seperate the two alkaloids to a large degree.

All theoretical, I havent tried it with anything yet, when I get a break from current projects I might give it a try with quinine or something.

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i was recenty talking to a newly graduated chemist, he was saying that methlybenzine is a better option coz he said it was'nt cancerous, carlslogenic, bad spleeing sorry. but i was asking questions about methods found on the net for extracting mesc.

does this help any??????????

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Carlslogenic...I like that!

Why not Carloslogenic

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"methylbenzene" (heh- he Must have been newly graduated) a.k.a. toluene has mostly replaced benzene in A/B extraction, happened decades ago, and yes- toluene is appropriate for alkaloids of lower polarity such as mescaline but would be unwise for the ergot alkaloids. In the US toluene is as available as cement (solvent section of any hardware store next to xylene, naphtha, acetone, MEK, etc..)- not sure about other countries.

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I think I'll bump this....

My blog contains some data on LSA extraction and analysis. It may be an on-going study.

One of the interesting comments to this point in this thread was that the essential oils of HBWR and morning glory may be the cause of nausea. This would be the basis of performing a non-poplar extraction before attempting an LSA extraction. This can certainly be investigated by performing GC analysis of non-polar extractions of the seeds. The one time I attempted this didn't demonstrate anything that appeared to be of significant concentration, at least in a methanol extraction that showed significant amounts of lysergamides present.

To the point, a methanol extract containing both polyphenolic glycosides and lysergamides by HPLC analysis had very little coming off the GC. This suggests either these compounds are not particularly stable to the over 250 C temperature of the GC inlet and/or chromatograph poorly. This would be the case for underivatized acids and lysergic acid derivatives.

It seems that the primary glycosides that do come out of the seeds are esters of caffeic acid. This can be demonstrated by HPLC analysis of hydrolyzed extracts, where the multitude of peaks observed in the unhydrolyzed extract convert to a single peak in the hydrolyzed extract. The UV/VIS spectra of these species match either chlorogenic acids in the unhydrolyzed extract or caffeic acid in the hydrolyzed extract.

chlorouv.jpg

http://www.cis.biochemj.org/bj/373/0987/3730987.pdf

I find little merit to the cyanogenic glycoside theory of nausea as this would have been much better documented if it was the case. Unfortunately, assays for cyanogenic glycosides require picric acid as a reagent which I don't have. If there is a potential agent of nausea, it could be some other glycoside, for example, a fatty acid glycoside. However, I can find no reference in the scientific literature that describes the determination of cyanogenic compounds in these seeds. I wonder if the discussion of cyanogenic glycosides arose from confusion of the term anthocyanins, as these might be more reasonably found. Just how much of a step would it be to confuse the terms "anthocyanin glycosides" with "cyanogenic glycosides"? In reality, the term "cyanin" doesn't have anything to do with cyanide. It probably has more to do with the color cyan.

http://en.wikipedia.org/wiki/Anthocyanin

What other fundamental questions about LSA containing seeds do you feel are worth investigation? My interest is in determining the composition of extracts of seeds of various sources and species and comparing them.

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I. muelleri is of high interest.

I believe if you look back through this thread someone questioned me on the cyanogenic glycosides and I provided at least something of a reference.

I think the general consensus amongst those who have done the research is that the nausea is caused by an essential oil or similar in the seeds that irritates the stomach, however you will be hard pressed to remove this "myth" from the books.

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having tasted the bittering agent,for a couple hours after a tiny bit,i dont want to repeat it!

cactus,rue,calea are all more pleasant to me!

t s t .

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