deacetylation->reductive methylation (via pictet-spengler conditions (heat and H+))

There has recently been discussion in the "entheogenic effects of NMT" thread of how 5-O substituted tryptamines are prone to oxidative cyclisation at the 4-position of the indole ring. This seems pertinent here as melatonin is a 5-oxygenated tryptamine. It could go that way via a Pictet-Spengler incorporating the acetyl group to form an azepino[5,4,3-cd]indole, or oxidatively at the sidechain nitrogen to form a pyrido[4,3,2-cd]indole, although to me the latter seems a bit less likely and requires basic conditions.

If the purported psychoactivity of O-methyl nordehydrobufotenine is anything to go by, the analogue corresponding to melatonin may show some kind of activity. But surely somebody must have looked into that by now?

I'm just imagining an acetyl group instead of that methyl group on the pyrido nitrogen:

Wow, this thread was hard to find! I am going to try the acetone extract... I thought I was going to have to freebase but luckily I found this thread. Thanks

(many months later)

I tried vaporizing some melatonin recently at 200 C in the Extreme Q. First dose was ~10mg. This produced very mild psychedelic effects (wavey vision) and a strong drowsiness, as if I was very tired. Slept well with very vivid dreams, woke up the next day feeling pretty sleepy, probably due to the high dose (10x normal).

Tastes vaguely like plastic, but not a gross taste like DMT, it's pleasant to vaporize. It's probably much more efficient to administer this way, especially before bedtime, since it starts working immediately.

Not sure if it's worth pushing the dose any higher. Maybe the psychedelic effects would be more pronounced?

I'm glad I was able to find this thread; the extraction/purification process seems simple enough. Maybe I'll give it a try one day.


arcologist: have you done any more investigation?

Have you ever tried mixing harmalas & melatonin? Good idea?

I have about 3.6mg melatonin sublingual along with a fat pinch of whole Syrian rue seeds, also sublingual, most nights before sleeping. Is this a good idea? Well, it doesn't appear to be acutely toxic… I'm not in a position to recommend it but I do get trippy effects on waking up. It's not possible for me to guarantee that this would be a positive lifestyle addition for someone with a regular normal job, nor that it will turn you into a hermit (as I seem to have become lately).

I'll weigh a 'fat pinch' of rue just to give a better picture of what that is, since my fingers are fairly dainty.