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extrememetal43
#1 Posted : 7/22/2008 8:59:20 PM
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When an alkaloid is in it's salt form it's seems it will always attach itself to whatever acid it is dissolved in right? ex. DMT acetate, DMT fumerate, Cocaine HCL, Mescaline sulfate etc. OK, now when these things are in there base form are they attached to anything? would they become DMT hydoxide or carbonate or anything like that or is that where they get the term freebase...so can you only get pure alkaloids in there base form?

 

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adrian89987
#2 Posted : 7/22/2008 9:17:38 PM
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That's where it gets the term freebase.

"Freebase (chemistry), the standalone basic form of an amine, usually an alkaloid natural product, as opposed to its water-soluble salt form."
 
Infundibulum
#3 Posted : 7/23/2008 5:30:11 AM

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Agree with adrian89987, alkaloids are called as such because they have alkaline (basic) properties. And this is because they contain nitrogen atoms, which, in organic chemistry can act as bases. Alkaloids are very weak bases and according to dissociation equilibria they are going to provide OH- only when there are sooo little OH- in water (i.e. under acidic conditions).

As an example, if one considers one of DMT's nitrogens (let's take the one with the two methyls attached) its behaviour in solution is going to be:

N + H2O <-> NH+ + OH-

In a very basic solution (pH>10) there are plenty of OH- around and the reaction will be shifted towards the left hand, giving you non-ionized nitrogen. So, you have the freebase form in basic solutions

In acidic solutions (pH<5) OH- concentration is very low and DMT's nitrogen feels the need to supply some OH- to the solution, so the reaction is shifted to the right. By doing that however, your nitrogen is ionized (it gets a positive charge!) In this state it can associate with the negative ions of the acid that made the acidic solution (be it HCl, citric acid, carbonic acid etc) to give you the respective salt form. It is the exact same thing with almost all the rest alkaloids.

Hope that makes sense


Need to calculate between salts and freebases? Click here!
Need to calculate freebase or salt percentage at a given pH? Click here!

 
shopdropper
#4 Posted : 7/24/2008 4:23:01 AM
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yay random chemistry question thread ! heres a question unrelated to the one above.

Someone i know just ordered 500 g of Peruvian Torch cactus to preform a mesc extraction. The Teks he has read say to use Xylene. then someone said that said that Toluene gave a cleaner product. this friend cant find Toluene(ANYWHERE!?!?), but has stumbled upon Methyl Ethyl Ketone! can this be used in place of the Xylene-Toluene? what are some other good uses for MEK its a list 2 chemical for a reason!
 
benzyme
#5 Posted : 7/24/2008 4:27:33 AM

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it's an alternative reagent used to synth amphetamines, and is more polar than either toluene or xylene

stick to aromatics (or an aliphatic) rather than a ketone, for your non-polar solvent. xylene only differs from toluene by one methyl group
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Noman
#6 Posted : 7/24/2008 8:55:47 AM

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Yeah MEK won't work at all for extraction though some say that one can recrystalize mescaline HCl with it.
In my friend's experience, toluene and xylene are pretty much the same for pulling mescaline since you're salting out the alks anyway.
 
 
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