Hi all,

DMT is a molecule with reactive potential. Under certain conditions it can get modified to form other products with known or unknown activity. Two of the most common modifications people are aware of are:

1) its oxidation to DMT-N-Oxide, This process is triggered by the presence of oxidising agents, most notably atmospheric oxygen, in which case it oxidises in a fairly slow pace. Other oxidising agents like peroxide, potassium permanganate or potassium dichromate can oxidise it much faster. But whatever the way, the molecule changes. It is an yellow oil as a freebase, and it has slightly different activity than unoxidised DMT.

2) its deamination to indoleacetic acid (?). This is what the MAO system is most likely doing to DMT, creating a totally inactive compound.

But how about other possible reactivities of this molecule? Two possibilities are taken from TIHKAL, shown below:

1) cyclisation to a b-carboline. I am currently unaware under which conditions this would happen. I am also unaware of the activity of such a product.

2) N-demethylation to NMT or tryptamine. Again, I am unaware of any conditions that could make this happen or about the activity of NMT.

So, the question is: to what extent home extraction techniques provide the conditions for such derivation products to happen? Home extractors are aware of the fact that DMT will oxidise and take precautions to stop it, e.g. store it away from heat, light, air. But how about the other potential byproducts? Could for instance a very high or low pH or even FASA somehow affect the integrity of the DMT molecule? Could they cyclise it to a carboline? Or demethylate it to NMT or tryptamine? Can they brake it down to just indole or scatole?

DMT synthesis is prone to goofy by-products, such as NMT or tryptoline or whatever-may-you. Could the standard extraction techniques per se be able to modify the DMT molecule as they extract it in some way?

very good thread.. new input will be very appreciated

what about the supposed reaction with DCM ?

It is alleged to be only a rumour. 69ron once posted that SWIH does not believe in the chlorination derivatives of dmt with DCM. He cracked it down by purposefully trying to make this elusive chlorinated compound, with no success at all. DMT stayed DMT and only DMT. If the chances of making this compound when you want it are so low, then the chances of not making this compound when you don't want it are really really big!

SWIMs imaginary friend has checked the purity of dmt extracted by STB and A/B methods and found it to be very pure by GC. Although dmt n oxide will not show up by GC methods as the heat SWIM believes changes it back into dmt (but unsure about this).

If the chlorination occurs it would occur at levels that are not detectable by simple bioassays one would need some kind of analytical equipment. its not just a rumour there is a full fledged paper on the subject. however does it happen in kitchen set up is still open to debate.

But in GC-MS both dmt and say, its putative cyclised beta-carboline by-product would show up as very very similar, right? The latter compound should have an MW lowered by 2 when compared to dmt. Does the main dmt peak in MS outputs also have satellite peaks around it? If yes, could this indicate possible existence of the said by-products?

there retention times would be a bit different and thus show up as small seperate peaks. but yes there are sometimes very small peaks in some samples swim has looked at but swim never went into much detail on these kinds of analysis. there fragmentation pattern would probably also be a bit different.

Not true, not true. ILPT experienced this or/and some other chlorinated byproduct when he performed a/b on chalipogna. Lack off money and chemicals forced him to use this stupid combination:vinegar, ammonia and DCM as NP solvent.
Saying wrong chosen combination ,because suspensions formed during neutralization created emulsions later on, during NP pulls.
His product was contaminated with something chlorinated he believe.It feel cooling like mentholic sensation on the windpipes with hint of some chlorinated organic compound. He is pretty sure with this. He has a huge experience with halogenederivates.

He doesn`t know what reaction led to this byprodutc. It was warm end of summer sunny and emulsion were sitting few days around, maybe some unpredictable radical reaction. Also ammonia was present all the time, so it`s really hard to say what was created.
Spice still potent so compound was either potent or coversion was minimal

But still, was it some halogenated derivative of some random chemical that might have been pulled through or was it a halogenated tryptaminic molecule?

And even if by some weird process dmt does get halogenated to some chlorinated derivative via DCM, does anyone has any indication that this may be harmful?? It may as well be more trippy and as such something to look for!

This thread at bluelight shines some light on the matter... some blue light, that is:
http://www.bluelight.ru/...?s=&threadid=177688
Dunno whether 'twas DMT or jungle spice being converted tho... but someone got a b-carb out of mhrb using dcm.

SWIM is quite convinced that some kind of beta carboline like structures are present in MHRB. They may be breakdown products of yuramamine or dmt or something else or just be there. Based on analysis of "jungle spice"

Burnt, can you give the details of that analysis? DMT can definitely be turned into a betacarb depending on how it's handled. I recently found this reference on the dea's microgram bulletin:
3. Brandt SD, Martins CP, Freeman S, Dempster N, Riby PG, Gartz J, Alder JF. Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis. Forensic Science International 2008;178(2-3):162-70. [Editor’s Notes: DMT reacts with dichloromethane (methylene chloride) to give a quaternary N-chloromethyl ammonium salt, which undergoes rearrangement during GC/MS analysis to give 3-(2-chloroethyl)indole and 2-methyltetrahydro-beta-carboline. Exposure of DMT to dibromomethane and 1,2-dichloroethane gave the N-bromomethyl and N-chloroethyl quaternary ammonium derivatives, and their various rearrangement products were characterized by GC/MS and NMR spectroscopy. Contact: Institute for Health Research, School of Pharmacy and Chemistry, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.]

SWIM will look through friends notes sometime soon. Also I think jungle spice has been compared to white spice and the product was only noticed in the jungle stuff. A fresh new analysis is needed in the near future.