Let me start by saying that I've never posted on this forum, so sorry if this is in the wrong place. Also, I've never used any drug for recreational purposes nor do I plan to, I am rather interested in the chemistry behind some of it though and that's what I'm asking about. So please don't tell me "go get some cough medicine with only dxm in it." Anyway onto the question. So I have 3/4 of a bottle of cough medicine containing DXM of course (15mg/5ml), doxylamine (content not shown), and acetaminophen (500mg/5ml). From what I know about acetaminophen, it does not dissolve well in water, although DXM does. So theoretically, if one were to shake up some cough medicine mixed with water (3:1 water/cough medicine was suggested) containing both ingredients, then filter using a shirt or paper towels or something, what would be left is a liquid mixture containing DXM, but not acetaminophen. As for the doxylamine, all I found is that it is toxic in high doses. Can someone please tell me if my logic on the water extraction is totally wrong and/or if the doxylamine will be filtered out of my solution with the acetaminophen. If I have this wrong, could you suggest another method of CWE/HWE and explain why it works instead? Thanks a ton!
DXM HBr Water Extraction?
- Thread starter Snoke
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Bluelighter
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I would not take it due to the doxylamine considering you aren't given the dosage.
High dosages of anti-histamines can be dangerous at worst and delirious in their effects at best.
There's plenty of DXM only cough medication, the Robitussion gel caps are the best for me.
Also the solubility for acetaminophen may be for the freebase form, salt forms of organic compounds tend to be highly soluble although I'm not sure specifically regarding APAP
High dosages of anti-histamines can be dangerous at worst and delirious in their effects at best.
There's plenty of DXM only cough medication, the Robitussion gel caps are the best for me.
Also the solubility for acetaminophen may be for the freebase form, salt forms of organic compounds tend to be highly soluble although I'm not sure specifically regarding APAP
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Depending on the pKa's of either substance it may be possible to selectively convert DXM HBr to freebase and then perform a liquid-liquid extraction with diethyl ether, which doxylamine is sparingly soluble in however I couldn't find any actual values for the solubility of doxylamine in ether.
Given that doxylamine dosages are around 5-10mg there is likely such a small mass of doxylamine in there that it will fully dissolve in the ether anyway.
Also in my analytical chemistry labs we did one where we extracted DXM HBr from cough syrup using toluene in a liquid-liquid extraction, but I don't think this cough syrup would have had doxylamine in it and there are no values I can find for doxylamines solubility in toluene.
Aside from that the only other option may be extraction with an alcohol and then a type of column chromatography to separate the compounds.
Honestly though all the above solutions are WAYYYY more difficult compared to simply buying a different brand of cough syrup, it's not like cough syrup is a rare commodity.
Given that doxylamine dosages are around 5-10mg there is likely such a small mass of doxylamine in there that it will fully dissolve in the ether anyway.
Also in my analytical chemistry labs we did one where we extracted DXM HBr from cough syrup using toluene in a liquid-liquid extraction, but I don't think this cough syrup would have had doxylamine in it and there are no values I can find for doxylamines solubility in toluene.
Aside from that the only other option may be extraction with an alcohol and then a type of column chromatography to separate the compounds.
Honestly though all the above solutions are WAYYYY more difficult compared to simply buying a different brand of cough syrup, it's not like cough syrup is a rare commodity.
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The Agent Lemon Tek won't work to remove the doxylamine and the acetaminophen since the pKa of each compounds respective amine groups are very similar, ~9.5.
This means the ammonia basification (deprotonation) step in the Agent Lemon tek would convert all three compounds to their freebase (water insoluble) forms non-selectively and with similar proportionality.
Similarly, the subsequent acidification (protonation) step would turn the freebase forms of the compounds back into their ionic salt (water soluble) forms, with similar proportionality.
Honestly I don't think there is any simple way to remove those other compounds, if there were, someone else would have discovered it by now.
I would say your best bet would be to remove as much APAP as can be removed by liquid-liquid extraction with chloroform as the organic phase, followed by conversion of organics to their freebase forms, and then running them through a well-designed column chromatography set up.
This means the ammonia basification (deprotonation) step in the Agent Lemon tek would convert all three compounds to their freebase (water insoluble) forms non-selectively and with similar proportionality.
Similarly, the subsequent acidification (protonation) step would turn the freebase forms of the compounds back into their ionic salt (water soluble) forms, with similar proportionality.
Honestly I don't think there is any simple way to remove those other compounds, if there were, someone else would have discovered it by now.
I would say your best bet would be to remove as much APAP as can be removed by liquid-liquid extraction with chloroform as the organic phase, followed by conversion of organics to their freebase forms, and then running them through a well-designed column chromatography set up.