I'm not entirely sure this is the right place to post this, i've just been asked by someone about whether it would be possible to separate the different tryptamines in an organic extract, or more to the point, how to separate the 5-meo and 5-OH dmt from the NN dmt.
My first thought in this direction was using recrystallisation purification. in the merck it says this about crystallising dmt freebase:
Crystals, mp 44.6-46.8. pKa 8.68 (ethanol-water). also reported as plates from ethanol and light petroleum, mp 46 (fleming, woolias). bp 60-80. pKa 8.68 (ethanol-water). Freely sol in dil acetic and dil mineral acids.
is this saying that a mix of ethanol and light petroleum (naptha? toluene?) can be used to recrystallise dmt?
some more info from the dmt entry in tihkal:
In principle, DMT is contained in the filtrate along with NMT and tryptamine itself. The tryptamine can be removed based on its ether insolubility and the NMT by its conversion to the benzamide with acetic anhydride or benzoyl chloride. The remaining basic material is largely DMT which can be further purified as the picrate salt.
okay, this information is of some use. tryptamine is sometimes present in plant sources, so being able to eliminate it is handy, but not all *that* useful. Removing nmt is more interesting however, as this material is inactive, well, virtually inactive, and often in high proportion to the dmt as it is an intermediate in the methylation. it's dead weight in the material, more smoke to inhale that's not getting you anywhere.
Now, the last thing is to be able to eliminate the 5-substituted tryptamines that we may or may not want or perhaps want to separate. I have only two ideas about how these will be separated.
The solubility of 5-meo and 5-OH dmt is diferent to each other and different to the dmt. one has an alcohol group, the other has an ether. perhaps the right combination of solvents would permit selectively precipitating the desired or undesired material from the solution. The solubilities of these materials could be enumerated in a wide range of solvents, and then tailor a mix that favours one or more over the other materials to become insoluble.
How can we change the solubilities of these even more so because of the presence of their particular functional groups, through a gentle chemical process which does not damage the rest of the alkaloids? In the case of the bufotenine, could we esterify it? that would make it less polar (?). acetic anhydride was suggested to remove the nmt in that synthesis, what would it do to 5-meo dmt and 5-OH dmt?
After removal of the solvent from the pooled extracts, the residue (an amber oil, 1.04 g) was distilled at the KugelRohr. A white oil distilled over at 130-140 °C at 0.1 mm/Hg, and crystallized spontaneously. This distillate weighed 0.77 g, and was recrystallized from boiling hexane after decanting the solution from a small amount of insolubles. There was thus obtained 0.40 g of dimethyltryptamine (DMT) with a mp 67-68 °C. The distillate contained about 3% of 2-Methyl-1,2,3,4-tetrahydro-b-carboline (parent peak mass 186, major peak mass 186) as an impurity which was lost upon recrystallization.
i have observed that recrystallisation out of a boiling pentane/heptane mix (shellite) of acacia obtusifolia extract there formed two major different substances, which would form inclusions if cooled quickly but the slower cooling was done (a cooling/warming process was used to substitute for insulated containers etc). there were cubic crystals of a semi-translucent white material, and a semi-liquid yellow which was fluid enough when removed from the crystals, which were attached to the glass, simply by swirling and loosening it first and then quickly decanting the mother liquor, a little wash with a pipette of ice cold naptha useually was enough to get it to the point the material was a very faintly offwhite colour.
In the case of these alkaloids, this is not enough to separate them in any way, i figure that the crystalline material is actually a mixture of nn dmt, nmt, 5-meo and possibly some tryptamine. knowing how to selectively remove these chemicals with some kind of process that does not damage them would be very useful to make the utilisation of high bufotenine content plants more possible. it would also permit the separation of the nn from the 5-meo which would be good for experimenting with them separately or reblending them in different proportions.
also, the other point about the quote just above is that dmt can be distilled. although, is that other chemical mentioned a side product or an oxidation product? also, what level of operator skill is required to run a kugelrohr?
To obtain the HCl salt of DMT, the residue was dissolved in anhydrous Et2O and saturated with anhydrous hydrogen chloride. The resulting crystals were recrystallized from benzene/methanol to give N,N-dimethyltryptamine hydrochloride with a mp of 165-167 °C. The yield from 14 g of the amide was 13.3 g of the salt.
heh, the old hydrochloride salts thing again... recrystallised in benzene/methanol... would toluene/xylene and ethanol substitute okay? maybe if it was all freshly dried solvents?
but digressing onto another sidebranch, what about salt solubility differences. and can other of the tryptamines crystallise as salts... (no don't answer that, i'll go and find out and post the info)
