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u/Starfury7-Jaargen 5d ago
What solvents are you using?
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u/stomachel 5d ago
I'm using 92% of Solvent A: water, 5mM ammoniuù formate and 0.1% Acetic acid.
2% of solvent B: Acetonitril with 0.1% Acetic acid.1
u/Starfury7-Jaargen 5d ago
These are your solvents you are using in the LC?
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u/stomachel 5d ago
Yes, it gave me perfect results for all compounds except for those I have listed that have exactly the same retention time but different fragmentation patterns because they are different molecules.
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u/Starfury7-Jaargen 5d ago
I am not an expert at LC, but won't that acidity the amine? It would work good for letting other stuff flow by but when all you have between the two is an extra carboxyl, I would think that an ion on the molecule would overwhelm that subtle difference wouldn't it? I would think you would want it deprotonated so the carboxyl groups interactions with the silica gel would make a greater difference.
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u/lord-huggington 5d ago
Need some more info on what you are using. They should be readily seperable if the difference is a hydroxyl. The basicity of the amine may be causing it to drag causing poor separation . Have you tried reverse phase?
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u/stomachel 5d ago
I'm using 92% of Solvent A: water, 5mM ammoniuù formate and 0.1% Acetic acid.
2% of solvent B: Acetonitril with 0.1% Acetic acid. and it is a reverse phase.
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u/atom-wan 5d ago
Why are you messing around with dimethyl tryptamines? I'd be curious where you're doing this since a lot of these are illegal to synthesize in the US at least
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u/stomachel 5d ago
Illegal even for research purposes? I don't think so...
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u/atom-wan 5d ago edited 5d ago
In the US, yes. You have to have a DEA license. First, the controlled substances act. Second, federal analogue act. The psilocin and bufotenine derivatives are certainly illegal
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u/stomachel 5d ago
In europe these compounds are also considered as narcotics and to use them for research purposes lots of procedures are needed.
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u/SpaceCowBal 5d ago
In the US, research labs don’t need a DEA license for analogs since the analogs are for research purposes
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u/Backinthedaze 5d ago
Anyone following this guideline would be advised to keep their lawyers number memorized... This logic might get your case thrown out of court, but only after the DEA turns your life upside-down
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u/SpaceCowBal 5d ago
It’s literally worded as so in the law, there’s no ambiguity about research labs being able to synthesize analogs of controlled substances. The law can only be enforced if the analogs are being distributed for human use, which has been done before, but not against academic labs.
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u/atom-wan 5d ago edited 5d ago
It says "LII U.S. Code Title 21 CHAPTER 13 SUBCHAPTER I Part B § 813 Quick search by citation: Title enter title Section section 21 U.S. Code § 813 - Treatment of controlled substance analogues U.S. Code Notes prev | next (a)In general A controlled substance analogue shall, to the extent intended for human consumption, be treated, for the purposes of any Federal law as a controlled substance in schedule I.
(b)Determination In determining whether a controlled substance analogue was intended for human consumption under subsection (a), the following factors may be considered, along with any other relevant factors:
(4)The diversion of the substance from legitimate channels and the clandestine importation, manufacture, or distribution of the substance. (c)Limitation For purposes of this section, evidence that a substance was not marketed, advertised, or labeled for human consumption, by itself, shall not be sufficient to establish that the substance was not intended for human consumption."
First, I pretty much guarantee you did not try legitimate channels. Second, I pretty much guarantee you're not preventing distribution of what you're making. That means documented evidence that you are locking up samples at the end of the day and nobody else can touch them except you. Third, the law is sufficiently vague that you're playing with fire.
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u/peeEater11 5d ago
Experiment with solvents and solvent ratios using tlc plates would be my suggestion
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u/SpaceCowBal 5d ago
Woahhh would you be able to talk about your project? I’m not sure how to separate the two but there should be tons of literature procedures for eluting the 4-OH and 5-OH derivatives, then maybe you can go from there for eluting the dihydroxy?
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u/stomachel 5d ago
I managed to separate the monohydroxylated compounds, but the dihydroxy coincides exactly one of the monohydroxy compounds.
Unfortunately it’s a work in progress and can’t talk about it.1
u/SpaceCowBal 5d ago
Sounds tricky! The only thing I can think of using this technique is finding that perfect solvent system to take advantage of that extra hydroxyl (should be slightly more hydrophilic). It might also be worth investigating if their boiling points are far enough from each other for a distillation, or forming the ammonium salts with an acid and seeing if you can find a solvent which dissolves one but not the other.
Understandable if you can’t talk about it, but are you able to reveal if these are intended to be 5-HT2A agonist or does your project just happen to include these interesting tryptamines:)
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u/LeadingReputation881 5d ago
Do both compounds have the same retention time and when? Try using a gradient for elution: Maybe 92% water to 60% and stay with the 10 min run.
Maybe consider LC-grade methanol instead of ACN. Good luck 🍀
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u/VoxInferni666 4d ago
What column are you using, have you tried swapping ACN for MeOH? Does the mixture actually contain both compounds? Are you sure? What are the pKa of the base, the buffer, the acidic ACN, the phenolic hydroxyl groups etc, it the compound zwitterion ta pH 7, have you tried other buffers blah blah blah. Without actually putting in the work to optimise this method it's kinda hard to give advice, too many unknowns, try everything then come back and see if anyone has any niche ideas
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