stability of dmt in various solutions and crystals

[supernate]

an ab extraction of the famous alkaloids from M. hostilis root bark was interrupted. the abstract follows:
38g MHRB was pulverized and added to 2x500mL 3.15% HCl, filtered and washed with 2x50mL dil.HCl. this acidic sol'n was cleaned with 3x100mL napthalene and 100mL toluene, followed by a 100mL acetone wash which resolved poorly.
at this stage i had to pack up because my folks came home, so i threw the blood-orange solution into a dark, cool closet where it has sit for about a week.

question: do i have to worry about the n,n degrading in the acid solution (was 3.15% HCl too strong) and how do i deal with the 80 or so mL of acetone which was miscable in the stuff? is there a possibility of an acid catalysed reaction over the course of a week?

also, i have read many sources claiming that mhrb contains dmt in .57-1% by weight, but have also read sources claiming .57-1% dmt AND 5meo- by weight. does anyone have empirical data on the topic? all my previous extractions were simply divided into xPiles and smoked.
and is it possible to chemically separate the 5meo from the straight up stuff?

[Blind_Angel]

I don'T think that 3,15% HCl would be too strong because some suggest using Muriatic Acid which is around 30% HCl

[ClearLight]

No 5Meo has been reported in mhrb. That doesn't mean there isn't any... just hasn't shown up in ott's works etc... I do have  a batch waiting for analysis.. (so many projects so little time ).  If i can get it done soon i'll post results of 2 axis tlc w/ modified Van Urk/Salowski reagents as color visualization aids... (plates are still on order).

[starlight]

I have experienced almost complete degradation of dmt in acid solution over the course of six weeks in the dark at room temperature. The same extract when processed immediately yielded .4% dmt.

[Urupeh]

swim think that more time the plant is soaked in the acid solution was better, swim in his dreams let the acid extraction run for one or two months, but reading the previous post swim know yet he was doing all wrong...what is the best time for extraction, to pull the major quantity of goodies out of the plant preventing minimal degradation? And how stable is DMT (free-base)in cloroform and in alcohol?, swim prefer dmt-free-base in solutions because in his dreams it is easyer to handle (put on a cigar or ading to plant material for pipe or simple put one or two drops in a glass tube...

[Nicodem]

A few times I prepared a solution of freebase alkaloids from Piptadena coubrina in DCM or toluene. In both cases they completely degraded in just few days. You better isolate them in a salt form. And about the acetone, if you leave an acidic solution of acetone standing for few weeks it becomes dark and nasty smelling (some condensation products form). I would not wait much if I was on your place even though I think these alkaloids are stabile in acidic medium. Many freebase tryptamines are still sensitive to oxygen and light even when isolated so always keep them in dark.

[zwackelmann]

though I cannot specifically answer your question as to stability in 3.15% HCl I got a few facts on DMT-extraction, which might help you and I got some questions too.
Questions first:
-How do you wash your acidic extract with naphthalene (a crystalline solid) - do you mean tetrahydro-
naphthalene?
- What do you want to achieve with acetone-extraction? How do you think to get a phase-separation when you wash with a water-miscible solvent?
Now the facts:
-DMT is best extracted into water with weak acids such as citric acid, acetic acid... Most DMT-salts are freely soluble in water (the oxalic acid salt is a little bit slower to dissolve - so better avoid, but oxalic acid got other merits - see below), so no need for HCl.
-Washing is probably best done with acetic acid esters. The ethyl ester is workable, but is quite soluble to some extent in the aqueous phase. The isopropyl ester or butyl ester is better suited.
-After freebasing the acidic plant extract DMT-base is best taken up in some kind of ether (MTBE works fine), avoid DCM as it is prone to react with DMT. In DMT worked up with DCM some 2-methyl-tetrahydro-beta-carboline could be found (GC-MS confirmed the presence of a peak with a molar mass 2 mass units smaller than that of DMT).
Acetic acid esters should do as well. I do not know how fast they hydrolyze when wet (to give acetic acid or acetic acid salts of DMT) on stripping off the solvent.
-The hydrogenoxalate and the hydrogenfumarate of DMT are sparingly soluble in cold ethanol and isopropanol. The hydrogenoxalate salts of many alkaloids are sparingly soluble in alcohol, some even in hot alcohol. The hydrogenfumarate salt of DMT has been used with success for purification (recrystallize from about ten times its amount of anhydrous alcohol - but isopropanol in somewhat larger amounts works too).
-Avoid solvents with fuctions that are prone to condensation reaction (ketones and many chlorinated solvents).
-Degradation of aqueous extracts of DMT could also be due to enzymatic attack - that´s why some researchers tend to extract first with methanol (usually a good solvent for alkaloids and naturally ocurring salts thereof). But methanol is going to extract also a lot of stuff you want to get rid of so acidic water extraction isn´t such a bad idea.

[Lilienthal]

I just don't see how a DCM deggradation product could cause a reaction to form the -2 mass. DCM by itself is absolutely inert and can't react with DMT. Your peak might have been something completely unrelated.

[zwackelmann]

Actually DCM is by far not as inert as many people would like it to be. Apart from its being suspected to cause cancer (DNA-alkylation) I´ve seen it to react with a variety of nucleophiles.
I know of an attempt to prepare malodinitrile by action of cyanide on DCM. No malodinitrile has formed, but there sure were some new peaks in the reaction mixture.
A mixture of toluene, pyridine and DCM prepared as GC standard (industrial recycling plant for pyridine) produced glistening white needles after a few days standing.
Toluene and pyridine alone don´t do that.
I was wondering myself at how DMT and DCM might react and since an alkylation must be the first step it is probably reaction with the terminal nitrogen to some kind of quarternary compound, which then reacts with the indole at 2-position, losing HCl. If one methyl of DMT gets lost (maybe as CH3Cl?), voilá - there we are: 2-methyl-tetrahydro-betacarboline.
Remember: DCM is also some kind of camouflaged formaldehyde!
Build a methylene bridge between the terminal N and the indole, split off a methyl, there you are.
Nasty stuff! Whenever you get a freebase in DCM, work fast, work at the lowest possible temperatures and be sure to remove all(!) of the DCM (hard vacuum, codestillation) as you work up.
Better still: Avoid DCM!

[Lilienthal]

Why don't you provide us with some serious literature links about such reactivities of dichloromethane? Until then I don't see a reason not to use DCM.