I am not sure if this is classified as synth talk, and if it is I apologize ahead of time and fully advocate the removal of this thread if it breaks any rules of the forum. I however am just curious about this and thought this would be the best place to get a good straight forward answer.

My question is simple. Is it possible to remove the N-Acetyl group from a molecule through means achievable by a kitchen chemist?

The following example is purely speculative and again, if this is considered synth talk I apologize. For a further understanding of what I am talking about however, I will give one example involving completely legal compounds.

I believe melatonin's chemical structure is 5-methoxy-n-acetyltryptamine. In theory, could the acetyl group be somehow removed to give 5-methoxy-tryptamine?

Edit: The chemical structure is actually N-Acetyl-5-Methoxytryptamine, not 5-Methoxy-N-Acetyltryptamine.

Unless you, or someone else comes up with a kitchen-safe procedure that doesn't involve dangerous/watched/ chemicals and protocol, then what you ask of is not allowed in the forum.

As far as I know, there isn't a kitchen chemist-friendly way to do what you ask, but who knows what discussion may bring?

Check this out:
http://www.tappi.org/Boo...hardwood-for-acetic.aspx

Not sure if this would work on Melatonin or not.

If you have any skill with tlc it would be a simple experiment. Melatonin and 5Meo-DMT will have rf.'s that differ significantly. 5Meo-dmt should have a very low rf (rf .1-.2 in 3/1 EtAc/MeOH) while melatonin should have a much higher rf (rf .5-.6 in 3/1 EtAc/MeOH)

You could also look for other procedures by searching using "Cleavage of acetyl group"

So then would discussion of said topic in the means of finding a kitchen chemist safe way not be allowed on the forum? It seems there are some fine lines between what would be allowed and what isnt, its a little confusing.

Sister, it seems you have to pay to download that paper. I shall have to search what you suggested though and see if anything comes up.

Eventually I want to go into organic chemistry as a profession and could figure it out then but that could be years down the road, who knows?

This site speaks of acetylating NMT to remove it from DMT.
This site speaks of using purified NMT as a psychoactive drug or psychoactive drug admixture.
It follows that removing the acetyl group from NMT (and thus, from any tryptamine) should be ok. The precedent was set by the discussion of NMT acetylation.
My books dont say much on solubilities for N-acetylNMT or melatonin. If its even marginally soluble in something like hexane then I expect one could combine N-acetylNMT, water, citric acid, and either (unscented) USP grade mineral oil or food grade paraffin wax, then maintain the mix on a light simmer for several hours. The acid water would hydrolyze the acetate, forming a dissolved citrate. The N-acetylNMT wouldnt be soluble in the water and without the oil or wax might stick to the sides of the pot or clump up, the oil or wax would be a vehicle to bring it back down and move it around more. Using oil, if the procedure wasnt complete you could just leave it in a bottle with acid water for a month. Using wax it'd be piss-easy to remove the wax- just let it cool and coffee filter it. Thats how my old pharmacy books say to deodorize opium, paraffin wax and a paper filter.
Seems kitchen friendly to me.

Dont wait, get a old OChem text book and a old CRC handbook of chemistry and physics and learn it on your own. Then when you do hit college your professors will love you.
Dont fear old CRC's, you'd be surprised how little they change. I have several and the one I most often grab is from 1954

Edit to say food grade paraffin wax is with the food canning gear at the supermarket- next to the mason jars, and USP grade mineral oil is in the pharmacy- its an old time laxative, imagine a greased pig going down a slide.

So the acetylNMT would stick to the wax? when filtered you have acetylNMT rich wax? Or would it remove the acetyl group and you would have only NMT stuck to the wax, and everything else in the water?

The prolonged boiling in acid water should get rid of the acetyl group.
Any remaining unreacted acetylNMT would be dissolved in or stuck too the wax or oil.

And the reacted NMT would be in the water?

acetamides aren't that amenable to acetyl cleavage, it may require more than simple reflux in protic solvents. basic hydrolysis may be more effective, but it'll still be a mess

All the hydrolyses of acetamides I've seen involve sodium hydroxide in ethylene glycol. Perhaps pharma grade propylene glycol would work for slightly food safer. It would then be a question of removing the alkaloid from the glycol - a non-polar extraction should work, but the high temperature basic conditions might do nasty things to your intended product.

What pH favours Pictet-Spengler cyclizations?

It may appear that way initially. Many of the reagents commonly used for the reduction or cleavage of acetyl groups are very hazardous. Meaning they may ignite upon contact with air or moisture, be explosive, carcinogenic or extremely toxic. These reagents require very special precautions, facilities, equipment. Discussions about reactions using these types of reagents are beyond the scope of this board, for reasons of safety and to avoid unwanted scrutiny of law enforcement types.

The procedure outlined in the paper that Sister posted above, uses nothing more than hydroxide ions (NaOH, KOH or CaOH). While these reagents need careful handling, they are unlikely to result in explosions, fire or the poisoning of ones roommates. They are also reagents we already use in almost any tek requiring a base, and are available to the public in hardware stores. If you misuse them, you are likely to be the only one injured. With the more hazardous chemicals, misuse could result in fires, explosions, poisoning and injury to the innocent.

Sister would say you can safely discuss any over-the-counter reagent and its uses on this board. Hazardous chemicals that can only be had from chemical supply houses and which cannot be legally shipped to individuals, not so much.

I was pondering on a efficient kitchen base procedure that would be fast enough so as to not decompose the tryptamine.
In aqueous media contact with the reagent would be the problem, perhaps dissolve the acetyl compound in a minimum of alcohol (perhaps supermarket 70% isopropyl or 70% ethyl) and stir a bit of lye into that. Regardless if it hydrolyzed or made the alcohol acetate ester the next step would be adding a NP and then water.

Just throwing kitcheny ideas out there

All good ideas and thoughts. It sucks that most of the procedures to do such things require such chemicals. Someone who has some analytical tools that could test the end product should try to find a kitchen friendly way of cleaving the acetyl group from molecules.

I would be happy to just go ahead and try some of the ideas mentioned in here, but I do not have the means to test the end product to see what exactly has formed.

Thin layer chromatography is going to be the easiest kitchen accessible way of following your reaction, as outlined in Sisters post to this thread. It will also tell you if you've destroyed the indole ring.

TLC isn't as difficult as it might seem. And it allows you to proceed with confidence once you get the hang of it. Especially if you have chemistry ambitions beyond extractions. You can get most of what you need from the TLCConscious kits advertised on this board; tlc plates and visualization reagents.

There was talk about this on a Zoklet forum, which I won't link to because they basically exist to violate the 'No Synth Talk' Rule, but some lab tests suggested that it can be done using Potassium Hydroxide. I won't go into here, but do some research, there are methods around.