So after exchanging some words with Trout, he mentioned the possibility of skatole impurities in DMT, and potential health dangers of it.

He mentioned he thought skatole might be in big part responsible for the smell of DMT, and that even Nick Sand said pure DMT has practically no smell. (My own hypothesis of the sharp DMT smell is different... I think that its in big part due to trace of other chemicals specially petrochemical solvents when they are used to extract, because when converting limo-extracted fumarates to freebase using the water crystallization method, the resulting DMT has nearly no smell, just a faint flowery smell. Also, the analysis of naphtha-extracted DMT which has the sharp smell, shows no sign of skatole)

In any case I had never heard of skatole being detected in these ethnobotanical plants either, so I went back through all the mass spectra of the substances Ive analysed so far. There is no evidence of skatole in any extraction of any Acacia, Mimosa nor Phalaris. Nevertheless, when looking at the spectra of Mimosa hostilis crude methanol soak, and the same for Acacia confusa stem and root, I´ve found a substance eluted at minute 3.07, that seems to match Skatole´s spectrum.. It has a molecular peak at 130, and the fragments seem to match.

But do notice that they are in very tiny amounts, the ratio of Skatole: DMT in Mimosa seems to be 1:121, and in confusa stem and rootbark is even smaller, 1:1604 and 1:1957. Since they were not detected in any of the extractions I tested (that used limonene, naphtha or xylene), I dont think we have anything to worry with extraction products, but is it significant for those ingesting whole brews?

The ratio seems very small, so in the case of Mimosa, if it has 1% DMT, it would have less than 0.01% skatole, and with Acacia confusa it would be ridiculously small. My gut feeling, taken together with the fact that ethnobotanical use seems to show no damage at all for those ingesting jurema brews, is that there is no problem, but I would just like to bring this up, maybe someone else has more input regarding this. Below im attaching the TIC and mass spectra of Mimosa hostilis and Acacia confusa, and of a Skatole standard to compare.

"Toxicity to Animals: Acute oral toxicity (LD50): 3450 mg/kg [Rat]."


http://mubychem.com/Skatole-3-methylindole.htm

Seems quite high..LD50 in rats is over 3000mg/kg..that is over 3g..so with the ammounts of mimosa brew people are ingesting there should be like microgram ammounts of skatole present. Doesnt seem like a thing to be worried about at all. For all we know it could be medicinal at that dose..many toxins are..take strychnine for example..in very tiny microammounts it is medicinal..take a bit too much and it will kill you for sure.

Do we know if skatole is even water soluble?

Wikipedia puts it as 'insoluble' in H2O. It's neither in my Merck nor CRC Handbook, that I can find. It's listed in the 2005-2006 Aldrich Catalog, but only has BP and weight.

I agree fractal, my feeling also is that in that dosage it wont be harmful at all, but I think its good to get this data out, at least for informational purposes.

Dozuki, I guess being insoluble in H2O is regarding freebase? In acidic solution it could very well be soluble.. one way to test this I guess would be to make a bit of acqueous solution of mimosa, let it dry/evap, and then analyze that...

Yes, I do believe that it is in reference to the freebase. And, yes, it seems it would be soluble in acidic conditions like other indoles. A tiny bit of digging on google shows that synthetic skatole is used in ice cream and perfumery amoung other things. Also, that in small quantities it has a sweet pleasant floral-ish smell.

jamie wrote: ..thats not particularly toxic..
..i think pure DMT gets an increasingly stronger smell over time..maybe this is the oxide or 2MeTHBC, but they would only be traces..
i've always thought the skatole thing has been exaggerated and this, thanks very much endlessness, seems to confirm it is not of much consequence in ordinarily extracted tryptamine plants..

Another particulary interesting analysis endlessness. I can't wait to show this to a good friend of mine who swears up and down that skatole is resonsible for the smell.

Mind you, this is with crude methanol soaks. There were no detected levels, not even seemingly traces, of skatole left in proper extraction products from mimosa, not even in jungle spice...

I think the smell of DMT is usually a mix of, normal DMT smell (earthy/flowery indole smell), plus traces of the solvents used (sharp more plasticky smell). I came to this conclusion when I crystallized freebase DMT out of water and it had distinctly softer smell than the naphtha-extracted products.