Mixing mushroom enzymes with tryptamines

[Mindlusion]

If a bio-transformation did happen, what could it give? Melatonin is interesting because the nitrogen that attaches to the acetyl group seems prime for methylation, similar to how tryptamine gets its second methylation when transforming to psilocin. One bio transformation possibility is shown below consisting of two simple steps (see first image where melatonin is in the first row, and the ~equivalent psilocin steps are in the second row).

Mass-spec would show a peak in the 262-264 range (see second image). It could be named 4-OH-5-MEO-MACT (where MACT = MethylACetylTryptamine). A close relative to it could be 4-HO-5-MeO-DMT.

To be clear, this is not a claim of a result, only discussing one of the possibilities there could be.

I doubt you will be seeing any N methylation on melatonin

NHAc is an amide and NH2 or NHMe are amines.

The enzymes for N-methylation are only for amines. Amides are a very different functional group, they are non basic (pka ~17) and very stable functional groups that are not easily cleaved. The properties of the amine are also vital for receptor binding in the brain, so that N-acetylated tryptamines or phenethylamines are not active psychedelics (unless first deacetylated invivo, maybe a pathway for melatonin).

Though as we have discussed in length, the other transformations are very possible.

 

[Loveall]

Thanks Mindlusion, makes sense.

 

[Mindlusion]

Thanks Mindlusion, makes sense.

Ah I missed that the suggestion for this product was from the mass spec peak at 264 m/z

The resolution isn't very good, it could be 263 (M+1).

and i was wrong before there are enzymes that can methylate amides, a quick google search told me so.

N-methylation of the Amide Bond by Methyltransferase Asm10 in Ansamitocin Biosynthesis

Ansamitocins are potent antitumor agents produced by Actinosynnema pretiosum. As deduced from their structures, an N-methylation on the amide bond is required among the various modifications. The encoded protein by asm10 belongs to SAM-dependent methyltransferase ...

www.ncbi.nlm.nih.gov

Perhaps not the N-methyl transferase that is the same for amines , but another enzyme.

Its the only real suggestion I can think of based on that data

 

[Loveall]

My bad, I just aluded to the MS. Below is the screen capture from Benz. This is preliminary and not confirmed, Benz would need to weigh in. The peak at 198 is background mobile phase I believe. For completeness also adding Dreamer's TLC (interesting spot would be on the top left).

Edit: looks like the images did not uplad properly sorry. Trying again.