toxic breakdown products from 'old' tryptamines?

[Jabberwocky]

Hello,

I have some 5-meo-DMT that has recently oxidized. I am told because it oxidized the dosage required is greater (to account for the material that is not 5-meo-DMT anymore because of oxidation). What is this chemical breakdown product? Could it be active? Is it toxic?

Is there any systematic way for knowing what a compound will break down into (like is there any rule of thumb for 5-meo tryptamines or something?).

I'm concerned. I plan on IVing this batch so I don't want to IV any toxic chemicals obviously!

Thanks! :D

 

[Ham-milton]

Well, the 5-methoxylated-T's are more toxic than the 4-hydroxylated (where I assume it'd oxidize).

I assume a higher dose would be needed, but don't just jump for a higher dose, start with a mg or two.

 

[Beenhead]

tryptophan oxidizes to N-Formyl Kynurenine, Wouldnt the same thing happen to a tryptamine? Obviously a derivative of...

 

[Coolio]

Tryptophan only becomes N-formylkynurenine when catabolized by the enzyme
Indoleamine-pyrrole 2,3-dioxygenase. The kynurenines have had the indole ring broken in addition to being oxidized by this enzyme. Oxidation alone is different.

 

[Beenhead]

Enzymes catalyze reactions, what oxidation is more energetically favorable in the absence of catalyst?

 

[Coolio]

Look at the structure of N-formylkynurenine:

It's no longer an indole, the pyrrole ring has been broken by the enzyme. It's oxidized as well, but you aren't going to have the indole ring broken apart by light, heat, and oxygen in a baggie or vial.

 

[Coolio]

http://www.erowid.org/chemicals/4_acetoxy_det/4_acetoxy_det_article1.shtml

http://www.shroomery.org/forums/showflat.php/Cat/0/Number/3133716


Multiple people chiming in that they think psilocin might polymerize when oxidized. The 1961 study linked to on the shroomery post theorized that the oxidation product in mammals is a quinone-imine or O-quinone of psilocin.


All of the cases reported in the RC scene say that their degraded products start to turn to black goo, which would mean something like this is happening and turning the tryptamines into dyes:

I don't see anything to worry about here, but you never know.

 

[hugo24]

How do you know that it has oxidized?Color alone doesen't say that much on the degree of oxidation,it usually overstates it.I have some 5-MeO's which have changed color,but analytics can't even detect it.

And hey,there are those who smoke that stuff,that means it is heated to 300°C or more,in the presence of oxygen and in fact it turned brown.But none complained about activity

 

[Beenhead]

So when does a change in color not imply a change of structure?

 

[Beenhead]

Look at the structure of N-formylkynurenine:

It's no longer an indole, the pyrrole ring has been broken by the enzyme. It's oxidized as well, but you aren't going to have the indole ring broken apart by light, heat, and oxygen in a baggie or vial.

right right an enzyme does things that are energetically unfavorable under normal conditions

 

[nuke]

Kynurenines make for some good coloring agents, so, it's possible.

Never had any ill effects from old tryptamines, nor loss of potency.

 

[Coolio]

Could a tryptamine's hygroscopic nature cause the visible changes? Ie. some of these indoles act as a dye like indigo but absorbing different colors, when they're in the presence of water molecules but not when they're in the form of dry crystals and crushed into dry crystalline powder?

 

[MurphyClox]

So when does a change in color not imply a change of structure?

I think you understood hugo24's statement wrong: He didn't say that a change in colour does not imply a change in structure. He rather said that the perceived change is often overestimated. And I agree, sspecially when analysis can't detect the impurities (what methods were used?). Fluorescent impurities suggest often even a greater degree of contamination.

Could a tryptamine's hygroscopic nature cause the visible changes? Ie. some of these indoles act as a dye like indigo but absorbing different colors, when they're in the presence of water molecules but not when they're in the form of dry crystals and crushed into dry crystalline powder?

This would normally not result in a brownish colour. If an indigo-like dye is participated, the colour is usually blue to violet.

 

[Coolio]

Not indigo-like, necessarily. Just indoles. I believe synthetic DPT is often colored yellow/orange (possibly DPT itself, possibly oxidation products), and I know extracted DMT has indoles like yuremamine and oxidation products that are red, yellow, and orange.

When a clear/white compound has a strong enough concentration of indigo or orange color dye in it, it looks brown to black to the human eye.

 

[yaesutom]

I once put a dose of 4-AcO-DMT in some water, and added a tiny bit of NaOH... let it sit for a while - the solution started to turn blue, then went to a dark blue-green, then i drank it down.. the trip definitely was different (not as pleasant).

 

[Beenhead]

I think you understood hugo24's statement wrong: He didn't say that a change in colour does not imply a change in structure. He rather said that the perceived change is often overestimated. And I agree, sspecially when analysis can't detect the impurities (what methods were used?). Fluorescent impurities suggest often even a greater degree of contamination.


This would normally not result in a brownish colour. If an indigo-like dye is participated, the colour is usually blue to violet.

I got that he said that just because you have color change does not mean that you have changed the chemical structurally. I then asked How do you know when you are dealing with just a change in color or a change in structure? I know that it would be very hard to tell with out taking, say a melting point, but maybe there is a visual clue... I doubt it though thinking about it freshly!

 

[Ham-milton]

look under it under different types of lighting (IR, blacklight, whatever) and see what is absorbed, what isn't.

 

[hamhurricane]

I once put a dose of 4-AcO-DMT in some water, and added a tiny bit of NaOH... let it sit for a while - the solution started to turn blue, then went to a dark blue-green, then i drank it down.. the trip definitely was different (not as pleasant).

thats very interesting, have you worked with 4-ho-dmt and did it seem more in that direction, could you elaborate on how it was less pleasant?

 

[vecktor]

I once put a dose of 4-AcO-DMT in some water, and added a tiny bit of NaOH... let it sit for a while - the solution started to turn blue, then went to a dark blue-green, then i drank it down.. the trip definitely was different (not as pleasant).

the blue colour would point to some hydrolysis of the ester followed by a truly tiny amount of the formed 4-OH DMT oxidising to the quinone. this seems to be the bluing reaction. I suppose that hitting the blue compound with a reducing agent should turn it back to 4-OH DMT, but perhaps the quinone is highly reactive and forms additional products.

 

[Riemann Zeta]

I thought that the primary "air" oxidation product of DMT and/or 5-MeO-DMT freebase was the respective quaternary N-oxide species rather than a ring-oxidized product. I believe that DMT and 5-MeO-DMT freebase do loose potency over time, even if stored at -20 deg in amber containers and I bet N-oxide formation is to blame. I would almost bet that something like DMT is less stable than the temperamental and easily-attacked LSD. Psilocin, being already hydroxylated, is different; I can see psilocin forming a quinone-ish species in the presence of oxygen and light, much like dopamine exposed to air and light will form semiquinones, then eventually dopachrome-like compounds.

Any hoodly doodle, I don't think the N-oxides of DMT/5-MeO-DMT are particularly harmful, they are just worthless--like any quaternary amine compound. If you don't like the idea of having an N-oxide hanging around, you can get rid of it by recrystallisation with an organic solvent.