High pH breaks down T's?

[Sledge]

Hi!

If you were to freebase a tryptamine (5-Meo-MiPT, DiPT and 5-MeO-DiPT) is there any chance that the pH becomes too high so the chemical breaks down? And what should the pH be to freebase a tryptamine?

Thanks in advance.

[Lilienthal]

You don't have to care about extreme pH during work-up as long as you wash out acids and bases carefully. But don't store them contaminated with acid or base or in solution for longer.

[ning]

How about concentrated NaOH in ethylene glycol at 150 C for 2 hours?  

By what mechanism does base cause breakdown of tryptamines?

[elfspice]

but i think it definitely would if it were boiled (ie the freebase) with NaOH present as the OH can cleave and become a highly reactive chemical (sodium), i'm not talking 100 or 200 degrees here though, i mean like in a basepipe, 250-400 (to be properly correct, superheated). What would sodium do to these alkaloids? I don't think it would be pretty.

in those conditions you mentioned, the dmt would boil out very very rapidly. the dmt would be all over the reflux condenser, if not lost to the atmosphere.

[Lilienthal]

Elfspice: That doesn't really make sense...  

ning: Tryptamines will probably split off an imine, leaving behind skatole. This is the typical smell of tryptamine and substituted tryptamines. Te mechanism is simply  a retro-Mannich reaction.