5-HO-DMT (Bufotenin) from Serotonin

[wikipedia]

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.

 

[xdragon]

Attitude Page - DMT-Nexus Wiki

wiki.dmt-nexus.me

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.

 

[dithyramb]

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.

 

[xdragon]

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.

 

[downwardsfromzero]

We won't be talking about iodomethane here:

Attitude Page - DMT-Nexus Wiki

wiki.dmt-nexus.me

[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...

 

[Brennendes Wasser]

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!

 

[xdragon]

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..

 

[downwardsfromzero]

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!

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