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Modafinil and phosphoric acid

C

coriolis

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Joined
Aug 21, 2007
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I don't know if I am posting in the right place but I think the following might be interesting. Yesterday evening I put for fun two tablets of modafinil (400mg) to a bottle with Coca Cola. I knew modafinil is practically insoluble in water. I drank the suspension of modafinil in Coca Cola in the morning. Since then I have a nausea and occasional flushes. I think it is transient and nothing serious. Could it be the case that modafinil reacted during the night with the phosphoric acid that is contained in the beverage?
 
there are a lot of other things in there too though.

still, I doubt that's it.
 
well, why not?

it is known that acids (phosphate) do hydrolise amides (modafinil), maybe to something like modafinic acid.
 
well, they catalyze the hydrolysis of primary amides with water present- but it must be at a pretty slow rate in this case because I'd imagine the much more powerful stomach acid would catalyze the reaction much faster.

that does make me think- is the active 'modafinic acid' or something else?
 
I think it is due to the caffeine in the cola.

Since I also get nauscious and heat flushes when I drink coffee when I have taken modafinil.
 
that does make me think- is the active 'modafinic acid' or something else?
Click to expand...

or is the reaction to slow to impair the absorption of the unchanged modafinil.
 
yea and provigil sometimes by its self when i would take 600-800mg will make u sick so i would think that does with caffein did it
 
Nausea is due to dopaminergic effects (in the CTZ), just as other drugs with dopaminergic activity (eg morphine, amphetamine, cocaine, nicotine) can make you do the big spit.

Amides are a hell of a lot more resistant to hydrolysis than esters etc., so I think a night in a cold weak solution of phosphoric acid is going to do bog all (N-formylamphetamine, which is an intermediate in the synthesis of said drug via the Leukhardt reaction requires hours of boiling in a fairly concentrated acid solution to hydrolyse it to amphetamine). If amide hydrolysis was that easy, proteins would fall apart in solution, which isn't too good for the evolution of life. As it is they require 0.1M hydrochloric acid and specific, dedicated enzymes - proteases such as pepsin & trypsin - to break them down in digestion
 
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