there is no such thing as L-tryptamine
the molecule loses chirality upon decarboxylation.

Nope - I'm stupid

Thanks for the kick in the face. I was wondering why I had never read anything on R,S or L,D dimethyl tryptamine - CAUSE IT AIN'T CHIRAL.

The decarboxylation of L-Tryptophan occurs (according to patent) 100% in acetophenone @ 130°C.

N-Methylation can be done a number of ways. I will continue to read up on them, but for the time being,

There is shulgins way of methyl-iodide -> quaternary methyl salt

But there is also a way, hunig's base, and methyl- or ethyl- bromide (depending on preferred ending).

I would assume purchasing hunigs base would rase some eyebrows at some chem places, but it may be possible.
Methyl Iodide could be synthesized, possibly, or bought ...

I am unaware of other n-alkylations for this, does anyone have any?

I will also be looking at ring opening methods for possibly making tryptamine derivatives.

Quote:
BEES,I've got a possitive result on my little DMT project,at last!!! DMT crystals!!!
I started with 10 grams of Tryptamine 98% witch I dissolved in 100 ml 2-propanol and mixed it with stirring 34 gram MeI and stirred this for 12 h at roomtemp. filterd it and washed it ones with a small amound of 2-propanol and let it dry.
I mixed 10 grams of the dimethyltryptaminemethyliodide with 40 gr4ams of ethanolamine 99% and boiled it for 15 minutes at reflux,let it cool down and put 100 ml dest. water to it on witch dissolved everything,extracted it 3 times with 50 ml ethylacetate,and back washed the ethylacetate sollution 2 times with 50 ml dest. water,destilled under reduced prassure most of the ethylacetate untill circa 40ml and let to evaporatted the rest of the ethylacetate with a little help by heating on the heater and vaccuum in a dessicator untill dry a possible got me some parafilm,put it in the refrigerator,and see all ready after a couple of houres nice small yellow DMT crystals! i thing around 4 grams or so

Hive:
Re: Variation on TiHKAL synth

Hai, Urushibara I would like to reply to your DMT sythesis questions: if you are looking for an easy accesseble route for making DMT and the yield is not your first consurn than you could the following route ((and YES I tright it out my self so I know it works!!))
All the chemicals you need are so far I know not watched, at least not in my country. Start with dissolving 10 grams of tryptamine in 100 ml of isopropyl alcohol and wen it all is dissolved (somtimes I warm it under the warmwatertap this helps to dissolve the tryptamine) put 30 grams of methyliodide (iodomethane) to it, you can use a erlenmeyerflask or a roundbotomflask of 250/500 ml and a stirringbar to stir and stir this sollution for the next 12 hours at roomtemperature, filter the formed N,N,N-Trimethyltryptamoniumiodide (or DMT-iodomethylate) and wash it 2 times with a little bit of isopropanol, press it dry between filterpapers and let it futher dry untill completely dry.
Then you take 10 grams of this tan-colored powder and mix this with 40 grams of ethanolamine cheap and very easy to get and reflux this in a roundbotomflesk with refluxcondenser for 15/20 minutes, give it a good boil. After you have let it cooled down you mix it with 100 ml demi water and extract this 3 times with 50 ml ethylacetate. Sepperate wash the ethylacetate one time with NaCl or CaCl sollution and 2 times with demi water, dry with MgSO4 destill of as much as possible under waterjetpumpvacuum the ethylacetate and put the residu in a small beakerglas and let evaporate, with heating, I use the heater in my room, of all the rest of the ethylacetate with ventilation of cors.
After that you with have a nice deep orange-golden oil, wich you crystallize by putting it in the freezer for the night an the next day you will have nice DMT crystals.

please someone try this. Also ..where is tryptamine to be found? The decarboxylation with spearmint oil and turpentine looks longwinded.

Aniracetam, have you ever tried this with a ketone catalyst by any chance? Many have recommended Carvone but someone recently has suggested cyclohexanon. Copper salts are said to work as well. One of these days I will get around to attempting a few decarboxylation catalyst but as it stands I have never really had a use for it.

I seem to recall something telling that the success with cyclohexanone was due at least in part, when it worked really well for a few people, to traces of cyclohexene in there.

Can't remember the details, and I have a nasty feeling that the flash drive that paper is on, is the one that died. Anyone careto refresh my memory? might be worth trying a cyclohexane/cyclohexene mixture for the decarboxylation.

I won't try it again for a while because it stinks up the place like indole (I live in an apt),
but if I did, I would do the reflux with mineral oil under argon.

the first peak in the chromatogram is the standard, second is product sample.

During her experiments with the above RXNs Ab2 gave some thought to why the 1st RXN failed so horribly and the answer AB2 came up with is that there was not enough catalyst, the 15 drop called for in "Student's" write up is well below stoichiometric amounts. And because it forms a shiffs base with the tryptophan which is only hydrolysed during the HOAc extraction, all the catalyst was spent before the RXN could go to completion. The ketone catalyst is only regenerated during hyrdolysis.

This theory vaildated by how quickly the RXN went to completion after the addition of an excess of ketone. So the lesson, if using a ketone catalyst is to use at least stoichiometric amounts, preferably a large excess. AB2 is at a loss as to how "Student's" rxn could have possibly gone to completion.

Acetophenone works so well, AB2 would never consider doing it any other way.

The difference between DMT and tryptamine is that tryptamine is not very soluble in either chloroform or DCM, while DMT is. So not sure how much of a problem that would be in this case. The tryptamine will remain in the aqueous phase, having little opportunity to react with the DCM. But one could always substitute EtAcO for the DCM to play it safe..

If Ab2 had extracted directly into HOAc instead of distilling first the DCM would not even be required! It was really just to break up the tar (polymerized acetophenone) that the DCM was required.

tryptophan is available in kg-plus quantities, as is 5HTP, for next to cunt all, thats why

Compared to what a bucketload of tosyl chloride and a kilo of indol-3-EtOH would set one back.

Ahem, when I said cyclohexene earlier, by the way, I meant to say cyclohexenONE/cyclohexane mixture.

Good news about the acetophenone, tried propiophenone by any chance? or think there any reason for it not to kick some serious CO2 arse into next week? As of course, propiophenone can be used for other things besides a solvent.

I think the ketone catalyst is important regardless of the solvent used, is there any reason to think that is not the case?