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Thread: Quinolizidine alkaloids and water

  1. #1 Quinolizidine alkaloids and water 
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    Hello, bright mind mates!
    I need to know one thing - and I cant find it in internet (maybe lack of skills) but...
    Does quinolizidine alkaloids (in particular - Lupanine and Sparteine) formate salts in aqueous solution? And if yes - what kind of them?

    Thanks for support.


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  3. #2  
    Bullshit Intolerant PhDemon's Avatar
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    These compounds are not very soluble in water, if you want to form salts in aqueous solution you normally make the hydrochloride salt, you do this by dissolving the alkaloid in equimolar hydrochloric acid.

    When you do this the nitrogen atom in the alkaloid accepts the proton from the HCl forming a positive ion, this ion forms a salt with the chloride ion left over from the HCl. These salts are very soluble in water.

    This is a common tactic to get insoluble drugs into the body. Look in your medicine cabinet or at your local pharmacy, you will see a lot of drugs that contain the hydrochloride salt of the active ingredient.


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  4. #3  
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    Quote Originally Posted by PhDemon View Post
    These compounds are not very soluble in water, if you want to form salts in aqueous solution you normally make the hydrochloride salt, you do this by dissolving the alkaloid in equimolar hydrochloric acid.

    When you do this the nitrogen atom in the alkaloid accepts the proton from the HCl forming a positive ion, this ion forms a salt with the chloride ion left over from the HCl. These salts are very soluble in water.

    This is a common tactic to get insoluble drugs into the body. Look in your medicine cabinet or at your local pharmacy, you will see a lot of drugs that contain the hydrochloride salt of the active ingredient.
    Well...I have used sonification on seeds. And I know that water where was sonification made contains those alkaloids, but I need to know in what salt form they are.
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  5. #4  
    Bullshit Intolerant PhDemon's Avatar
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    If they are in solution in a salt form they will be the hydroxide salt. The molecule will take a proton from the water and form a salt with the hydroxide ion left behind. I wouldn't have expected this to happen though, I would of thought the alkaloid would just sit there!
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