Looking at the two molecules, serotonin, a common neurotransmitter and one of the most potent psychedelics in the world, bufotenin aka 5-HO-DMT are very similar, just with the two nitrogens replaced with methyl groups.

Thus, could a substance such as Iodomethane or S-Adenosyl methionine be used to convert this readily available neurotransmitter into bufotenin via methylation?

Legally, of course.

https://wiki.dmt-nexus.m...chemicals_and_procedures
Most, if not all, useful methylation agents will give you cancer. You don't want methylated DNA, trust me.

To still answer your question: obviously it is possible (for a trained chemist), but it would require protection/deprotection of the phenol group. Furthermore, tryptamine chemistry can be rough sometimes. So in short: as long as you have to ask about it, forget about doing it. And even if you know the theory, it's still a bit of a way - and this is clearly the wrong site to discuss things like that

Also, Serotonin isn't easy to acquire in meaningful quantities, unless I am missing something. Getting access to bufotenin-containing plants (or animals) is easier, as far as I am aware.

İs there anybody familiar with the effects of bufotenine in any form of administration? İ would like to be able to differentiate it from the other tryptamines in experiences of plants that are said to possibly contain it together with other tryptamines.

If you have access to suitable pure compounds, TLC (thin layer chromatography) is a very good method to assess the purity of your extracts. As psychedelic experiences will always be very subjective, judging the purity/alkaloid profile of any drug/plant/whatever [by bioassay] is not a clever way to go about things. And it can be very harmful, considering the different toxicity profiles of common tryptamines like bufotenin, 5-MeO-DMT and DMT.

We won't be talking about iodomethane here:
https://wiki.dmt-nexus.m...chemicals_and_procedures
[EDIT: got distracted during composing this post and someone beat me to it!]

S-Adenosyl methionine is one possibility for a methyl source during biosynthesis. INMT will catalyse the transfer of methyl groups onto the side-chain nitrogen. This likely occurs after the decarboxylation of 5-HTP to serotonin, in analogy with formation of DMT and psilocybin.

Some reading material attached...

Just as a side note: Unlike Tryptophane, 5-HTP gets destroyed when trying to decarboxylate it with any common method. That phenolic OH- really is a bitch!

As 5-MeO-tryptophan can be decarboxylated, I would guess that decarboxylation of a suitable protected phenol group is achievable as well. But then again, none of this is the kind of chemistry welcomed here..

Yep. Living systems do some pretty impressive chemistry with their enzymes that we find hard to brute-force in the reaction vessel.