What is tryptamine anyway?
Tryptamine is an alkaloid found in trace amounts in brains, plants, and fungi. While thought to be biologically active itself, its main interest is in the fact that it forms the backbone to many other biologically active compounds. This includes hormones, neuromodulators, neurotransmitters, medication, and (of course) an array of psychedelic drugs. You may have heard of serotonin (neurotransmitter associated with happiness), melatonin (hormone that regulates the circadian rhythm), sumatriptan (medication that treats migraine headaches), zolmitriptan (medication that treats acute migraines), psilocybin (found in shrooms, a popular psychedelic drug), and DMT (a famous US Schedule I psychedelic drug known as the spirit molecule which makes users have OBEs into hallucinogenic alien vistas). These are all derivatives of tryptamine.
Cool! Tally-ho chem-nerd!
There are several ways to go about synthesizing tryptamine, but the most accessible means is by decarboxylation of tryptophan. Tryptophan can be bought in bulk since it’s a dietary supplement. Don’t buy it in capsule form because it will have other inactive ingredients that you don’t want. Tryptophan can also be synthesized from milk if you really feel DIY.
How do I go about this decarboxylation?
Again, there are several ways to do this, but there’s one that’s my favorite. In order to remove the carboxyl group, we need energy to do it (currency of the universe). We also need a catalyst so that the molecule knows, so to speak, what to do with the given energy. A catalyst is not consumed in a reaction, in simply aids in the reaction. Finally, we’ll need a solvent. A solvent dissolves the solute, tryptophan in our case, which essentially allows our catalyst to work on the solute. Note that the tryptophan isn’t actually chemically dissolved, but is suspended.
First, we’ll suspend tryptophan in a high boiling solvent (Tetralin, DMSO, Cyclohexanol, ect). Then we’ll add a ketone, our catalyst, to the solution. Different ketones will gives different yields due to their varying properties, but the commonality is their CO double bond which forces the carboxyl group out of the way. The best ketone to use would be pentan-2-one. Butan-2-one and acetone (propan-2-one) will also work well, but with a bit less yield. Cyclohexanone would also work, but to what yield I’m unsure. Finally, we heat the solution to reflux and vigorously stir until all the CO2 has evolved (evident by the fact that the solution has become clear).
Finally we treat the product (many ways to do this). The solvent can removed by evaporating under reduced pressure. The residue can then be crystallized with boiling benzene. The decarboxylation method described above can also apply to any alpha-amino acid. So get to decarboxylating! Anyways, that’s how you synthesize tryptamine.
Anthony's Musings 