Earlier today I started trying to piece together a possible route to DMT from indole-3-carbinol, which is readily available OTC as a health supplement.

This is a very rough sketch and likely has a number of flaws I haven't even begun to consider.  A part that may be a problem already is that it assumes chloro- or bromoformaldehyde can be produced without too much complication (something I haven't fully explored and may be more involved than I have anticipated.)

Also, the aldehyde protection method needs to be kept relatively inexpensive for this synthesis to be practical.  I used the box to stand in place of some generic protection procedure.

Dimethylamine boils at a very low temperature which would also have to be dealt with.

There may also be side reactions that need to be dealt with as well.

As I have said, it is still fairly rough at this point and any comments are greatly appreciated.

You're absolutely right.  I've even had a few other people look over it and somehow completely missed it as well.

I believe I was thinking about halogen additions to amines that form tetra-ammonium salts and having the 4 bonds thought stuck in the back of my mind for some reason.


I think the only realistic derivative of the procedure is to do something like adding cloroethanol to dimethylamine to get dimethylethanolamine.

Then halogenate indole-Ch2-OH to indole-CH2-X  (via Groove's process or similar,) make that into a grignard and add to the ethanolamine.

That would actually involve simpler precursors and avoid a reduction reaction.  However, the entire process has to be carried out in anhydrous conditions.

Dimethylethanolamine is actually available OTC in bulk supplements as its bitartrate salt, but the bitartrate would cause a mess with the grignard so the freebase or a friendlier salt would need to be formed and thoroughly dried.

I realized that to make and indole derived grignard reagent, the nitrogen on the indole ring would first need to be protected somehow or else nasty polymers would likely form.  I also managed to stumble across this..

http://designer-drug.com/pte/12.162.180.114/dcd/chemistry/dmt.indole.grignard.html

I don't entirely understand the reaction mechanism, been trying to find some related information.

Thank you for the explanation, it cleared a lot of things up.

Indole-3-carbinol is available in capsules as a health supplement.  It's supposed to act an an antioxidant and help prevent cancer or something like that.  Most OTC health supplements don't really do all that much and I'd imagine this is probably in the same category.

I think the majority of the routes I've been working out are overcomplicated crap.  After some more research and thinking, I believe the most sane route is probably oxidation of indole-3-carbinol to indole-3-carboxylic acid (via KMnO4) followed by decarboxylation to get indole.

From indole, adding things to the 3 position doesn't seem to pose too much of a problem, and there are multiple ways to accomplish it.

It feels kind of dumb stripping indole-3-carbinol back down to indole after essentially paying someone else to build it up from indole, but indole tends to be watched fairly closely and many chem supply houses refuse to sell it to the general public.  Some overseas suppliers will probably sell it, but having a kilo of stinking white powder with your name on it move through customs is probably less than ideal.

Interestingly enough I came up with a simmelar idea seperately not that long ago.
See this thread: http://127.0.0.1/talk/index.php/topic,680.msg7789.html#msg7789
DMT from Indole-3-Acetic acid (IAA) available OTC.

Thankyou for enlightening me about indole-3-carbinol though! Good luck with this idea too.