KemicallyImbalanced
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N,N-Dimethyltryptamine as fumarate salt
I'm trying to make the 2:1 fumarate salt of a well known tryptamine that has a molecular weight of 188.27 and since I will be using one gram of this
tryptamine in this experiment would an equimolar amount of fumaric acid be ~300mg? This is what I plan to do:
Add 1gm of the tryptamine and 300mg of fumaric acid in 10ml 95% EtOH with stirring until it's dissolved. Then 100ml of naphtha is added and the flask
is placed in the freezer for three days to precipitate the crystals.
How does that sound?
[Edited on 20-8-2006 by KemicallyImbalanced]
<sub>Edit by Nicodem: Changed title after thread merging.</sub>
[Edited on 25/3/2008 by Nicodem]
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Nicodem
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According to my calculation you would need 310 mg of fumaric acid or 320 mg to assure some equivalency. Using naphta to force crystallization is a
very bad idea according to experience. You can get it to crystallize, perhaps, but more likely you can get two phases, a paste or no crystallization
at all. Not to mention that the product would be contaminated with high boiling alkanes and smell like gasoline. Diethyl ether is normally used for
this purpose. If you can’t get ether than you can dissolve the 1 g amine in 5 ml acetone and add a solution of 320 mg fumaric acid in 5 ml acetone.
The fumarate salt should crystallize out if insoluble in acetone. You can then vacuum filter and dry. If soluble you should let the solution evaporate
to form crystals and then wash them with ether.
I hope you understand that it is absolutely necessarily that the salt exists in crystalline form in order to crystallize from any solution at all.
N,N-dimethyltryptamine (MW = 188,27 g/mol) does indeed form a fumarate salt so this should not be a problem if we talk about this compound. The
impurities can sometimes interfere with normal crystallization of amine salts.
Now, if you are determined to make the fumarate in order to purify the product you should also know that N,N-dimethyltryptamine is more easily
purified by recrystallization from petroleum ether. Also the free base form of N,N-dimethyltryptamine is the only useful form for the normal routes of
application (the fumarate is only useful for IM use, which is pretty scary to even consider and besides offer no advantage but many risks instead).
[Edited on 20-8-2006 by Nicodem]
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unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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KemicallyImbalanced
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What happened when naphtha was used to push the salt out of solution? Have you actually tried using acetone to make the fumarate?
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Nicodem
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Naphta is extremely non-polar and thus it either pushes a phase containing polar compounds (the ions, EtOH and H2O) out or does whatever else similar
that inhibits crystallization (at least in my and others experience with several hydrochlorides). If you don't believe me, you can check several posts
on several forums that explicitly mention that it is not possible to precipitate hydrochlorides of certain aliphatic amines from naphta or toluene
with HCl gas unless the solution is well dried. So, I tended to generalize that what is true for hydrochlorides could well hold true for any other
salt as well. Needless to mention, that anybody else would avoid using naphta simply because you can not completely remove it from the product (that's
why petroleum ether is generaly used as extremely non-polar solvent in organic chemistry and not naphta - it is easy to remove!).
As far as me having verified what I suggested, the answer is no for any tryptamine whatsoever. Also, you did not specify which exact tryptamine, so
how can anybody answer from experience?
If the compound is the one I extrapolated from the given MW, than you might forget about finding anybody ever having done it except for a strange
coincidence. The reason is that it would be plain useless to make a fumarate salt of a compound that is only useful in its free base form.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Coschi
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Help forming DMT.Fumarate salt
Hypothetical chemistry question
Say one had relative clean DMT freebase that they wished to convert to DMT.Fumarate, how would this be achieved?
I have looked at the numbers and believe the following calculations to be correct:
(Wiki) molecular mass of DMT: 188.269 g/mol
(Wiki) molecular mass of Fumaric Acid: 116.07 g/mol
So to convert 500mg of freebase DMT to DMT.Fumarate:
(mol_mass(DMT) * 2) / (DMT mg) = mol_mass(Fumaric) / (Fumaric mg)
... Fumaric mg = (DMT mg) * (mol_mass(Fumaric) / (2 * (mol_mass(DMT)) )
... Fumaric mg = 500 mg * 116.07 / (2 * 188.269)
... Fumaric mg = 154.13 mg
More importantly, how to perform the actual conversion?
I thought it would have been as simple as dissolving the required amount of fumaric acid in distilled water, adding the freebase and dissolving that
too (which it would as the pH has been lowered) and evaporating under heat or pressure or both?
That method did not work, well, not really
A water soluble hard-as-hell gum was produced. About 14mL of water was used and evaporated over ~45mins. Could that have been too quick?
How about mixing both amounts in a minimal amount of acetone or ethanol and letting it evaporate to dryness? same thing really isn't it...
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stoichiometric_steve
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if you do need to make the fumarate, you should use a volatile organic solvent such as the lower alcohols. if you get nice crystals or not mostly
depends on the purity of your free base and the counterion (i.e. the acid you'll use). it might be a better idea to use hydrochloric acid instead.
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DJF90
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I'm not sure if that would work the same way. The solvent can greatly affect the acidic properties. One such example is hydrogen chloride gas
dissolved in dry toluene. Dry indicator paper will turn green, no reaction occurs with magnesium, and no reaction occurs with calcium carbonate.
Therefore I conclude that using small amounts of ethanol or acetone is probably not not the same thing. Why bother using fumaric acid? Wouldn't it be
more economical to use citric acid instead? This board isn't drug orientated, and there are probably more appropriate places to ask this kind of
question, but seeing as this is "hypothetical" I guess it shouldnt bother me.
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Coschi
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The fumarate is the salt listed for human studies
I'm not sure why exactly, but I'm sure there was some basis to choosing the fumarate salt above others. perhaps bio-availability? I wouldn't think so,
but anyway..
Hydrochloride doesn't crystallise (perhaps it 'can', but in related literature it 'doesn't')
There isn't really any process as such to ensure the salt is formed is there though? Basically add the two in a solvent of some kind and that should
be it.. right?
By lower alcohol would you mean methyl and ethyl alcohols for example?
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grind
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I hope your question is really a hypothetical one.
It´s possible to work with acetone or isopropanol. Make a solution of your amine, make separately a solution of the acid (slight excess). Combine the
solutions and induce cristallization, if it not spontaneously occurs.
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Nicodem
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Coschi, there are two reasons that had me thinking to move this thread to either Detritus or Beginnings:
1.) you did not bother using the search engine and opened another thread on the exact same topic we already had;
2.) you are too lazy to even write the fumarate salt of what you want to make (acronyms like DMT mean absolutely nothing to the great majority of this
forum).
Obviously, both 1. and 2. indicate your laziness to which I always irrationally overreact. It's forgiven this time since you are new, but try not to
make me overreact again, OK?
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Coschi
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ha! Gee thanks for that Nicodem, great help you are
and very observent also
Admittingly, I am a lazy bugger.. However I did find this post before I posted. Pity it didn't answer my question whatsoever (as to calculations, not
to mention the specifics in my question), and note that the only informative response is actually incorrect (oh, you wrote that)
And, when was the last time you looked at your forums?
I see topics like:
"Lithium Al Hydride quick question"
"Salvinorin - finally a total synthesis"
"Melatonin: 5-MeO-N-Acetyltryptamine"
etc..
You think people don't know what DMT is?
you can always google DMT also.. I'm sure smart people like yourself can figure it out
Lastly, I find bumping previous topics rarely gets fresh interest. Sometimes it's fine, but sometimes, like with specific things that'd like to be
answered type, I find a fresh post works better
So, how's about you try not to overreact?
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Nicodem
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Well, obviously you did not search before posting since you neither posted in the appropriate thread nor added the link there in your original post.
And no, we do not support such arrogant laziness as: "you can always google DMT also". There is no point in inventing excuses or getting pissed. And
what is it with those thread titles you listed? None used acronyms. Instead of going off topic rather explain what exactly you don't understand about
this salt formation and complain trough the U2U if you must. What particulars about N,N-dimethyltryptamine salt crystallization you don't understand?
What in the ex-old-now-merged thread you did not understand? And why don't you search the literature for the experimental on how it's done?
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Coschi
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eessh, i've said my part, I don't need to justify myself to you
Here's a thought; in future when fools like myself make another such tremendous error, perhaps you give a more calm response, and actually give a
useful response also. You still get your say and don't look like a such prick. Also, when people in future do search for this topic, they don't have
to read through so much rubbish like your posts to get the information they're after
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Nicodem
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If you don't want to discuss the thread topic and just want to behave like an ignorant fool, then rather don't post anything. I don't have time for
childish members who rather blather nonsense instead of going to the library. Obviously preparing N,N-dimethyltryptamine fumarate is not your goal
since otherwise you would do it properly instead of that nonsense waste of material you described. For most people this amine is too precious to be
wasted that way, so reasonable people search the literature. Anyway, people like you certainly do not deserve the DMT experience, so perhaps it was
nature playing a trick on you. It's just evolution at work.
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