Why can't Fumaric Acid bind to NMT or DMT-n-Oxide?

[fathomlessness]

Chemically I mean. I remeber reading they wont but from some reading Infundibulum thinks it may be possible for oxides

 

[Mindlusion]

N-oxide is a weak base, with a pKa of 4.5, comparable to aniline. Amines are stronger bases usually with pKa's around 10. DMT is a fairly good base with a pKa of 8.6.

So amine oxides are basic enough to form salts with strong acids, fumaric is stronger than acetic acid, with a pka of 3.5 , so you could probably form a fumarate salt.

NMT can easily form fumarate salts, its an amine

 

[fathomlessness]

N-oxide is a weak base, with a pKa of 4.5, comparable to aniline. Amines are stronger bases usually with pKa's around 10. DMT is a fairly good base with a pKa of 8.6.

So amine oxides are basic enough to form salts with strong acids, fumaric is stronger than acetic acid, with a pka of 3.5 , so you could probably form a fumarate salt.

NMT can easily form fumarate salts, its an amine

Thanks for the reply. If DMT-oxide could probably form a fumarate salt then after I do a FASA conversion, what is it that is still left in the acetone that is still active? Left over dmt-oxide that wont convert?

Thats good news NMT can form fumarate salts (i thought i read somewhere that it couldn't). I just want as much conversion of all active alkaloid as possible but what is left in the acetone is still distinctly like DMT (but its not because FASA no longer crashes any more crystal out).

 

[Mindlusion]

N-oxide is a weak base, with a pKa of 4.5, comparable to aniline. Amines are stronger bases usually with pKa's around 10. DMT is a fairly good base with a pKa of 8.6.

So amine oxides are basic enough to form salts with strong acids, fumaric is stronger than acetic acid, with a pka of 3.5 , so you could probably form a fumarate salt.

NMT can easily form fumarate salts, its an amine

Thanks for the reply. If DMT-oxide could probably form a fumarate salt then after I do a FASA conversion, what is it that is still left in the acetone that is still active? Left over dmt-oxide that wont convert?

Thats good news NMT can form fumarate salts (i thought i read somewhere that it couldn't). I just want as much conversion of all active alkaloid as possible but what is left in the acetone is still distinctly like DMT (but its not because FASA no longer crashes any more crystal out).

Likely it is just DMT that didn't precipitate. Either because your acetone contains traces of water, or you did not acidify fully. But even anhydrous acetone will hold onto traces of DMT fumarate. You can put the acetone in the fridge or freezer overnight to help push out the crystals

 

[fathomlessness]

N-oxide is a weak base, with a pKa of 4.5, comparable to aniline. Amines are stronger bases usually with pKa's around 10. DMT is a fairly good base with a pKa of 8.6.

So amine oxides are basic enough to form salts with strong acids, fumaric is stronger than acetic acid, with a pka of 3.5 , so you could probably form a fumarate salt.

NMT can easily form fumarate salts, its an amine

Thanks for the reply. If DMT-oxide could probably form a fumarate salt then after I do a FASA conversion, what is it that is still left in the acetone that is still active? Left over dmt-oxide that wont convert?

Thats good news NMT can form fumarate salts (i thought i read somewhere that it couldn't). I just want as much conversion of all active alkaloid as possible but what is left in the acetone is still distinctly like DMT (but its not because FASA no longer crashes any more crystal out).

Likely it is just DMT that didn't precipitate. Either because your acetone contains traces of water, or you did not acidify fully. But even anhydrous acetone will hold onto traces of DMT fumarate. You can put the acetone in the fridge or freezer overnight to help push out the crystals

Woah, so if there was hypothetically water in the acetone, when you put the acetone in the freezer will the water (containing dmt-fumarate) freeze and sink?

 

[Mindlusion]

N-oxide is a weak base, with a pKa of 4.5, comparable to aniline. Amines are stronger bases usually with pKa's around 10. DMT is a fairly good base with a pKa of 8.6.

So amine oxides are basic enough to form salts with strong acids, fumaric is stronger than acetic acid, with a pka of 3.5 , so you could probably form a fumarate salt.

NMT can easily form fumarate salts, its an amine

Thanks for the reply. If DMT-oxide could probably form a fumarate salt then after I do a FASA conversion, what is it that is still left in the acetone that is still active? Left over dmt-oxide that wont convert?

Thats good news NMT can form fumarate salts (i thought i read somewhere that it couldn't). I just want as much conversion of all active alkaloid as possible but what is left in the acetone is still distinctly like DMT (but its not because FASA no longer crashes any more crystal out).

Likely it is just DMT that didn't precipitate. Either because your acetone contains traces of water, or you did not acidify fully. But even anhydrous acetone will hold onto traces of DMT fumarate. You can put the acetone in the fridge or freezer overnight to help push out the crystals

Woah, so if there was hypothetically water in the acetone, when you put the acetone in the freezer will the water (containing dmt-fumarate) freeze and sink?

No, it will stay dissolved (think vodka)