I think the problem is there isn't good stirring in the pressure cooker. The reaction mixture is mostly heterogeneous, good stirring and high temp seems necessary.

sodium dithionite is essentially an anti-oxidant, it increases the yield somewhat in the butanol prep. Best yield is when the reaction is done under inert gas though, nitrogen or argon. It doesn't act as catalyst.

Here is what the TLC should look like , when I ran the butanol reaction. Melatonin is the left lane and the product (mexamine) is the middle lane

Thanks, that's very helpful info. What did you use to develop the TLC?

thats MeOH:EtOAC:Et3N (85:15:1)

but your system should be fine and give similar results

Update: I now discourage using heat/pressure unless you really know what you are doing. The home vanilla extract bloggers (referenced above) using heat, pressure, and alcohol are a bit too wild for me . I'll stay within the safety of the Nexus, thank you very much.

That being said it does seem possible to deacelytate melatonin in IPA and NaOH. Below is a TLC image (sorry for quality), the strip on the left is from a heat/pressure experiment that ended abruptly. The strip on the right is reference melatonin. Using denatured alcohol + 10% ammonia (~50/50) as the developer, both strips have melatonin at the top, but a second lower sopt appears on the experiment sample. This lower spot is consistent with mexamine based on Mindlusion's TLC result posted earlier. Conclusion is that some of melatoninially deacelytated before the experiment came to an untimely end.

Next attempts will be without heat/pressure. Instead time will be used and IPA will be substituted by deantured alcohol (methanol/ethanol 60/40) from the hardware store. By using a smaller alcohol, NaOH solubility increases and the smaller alcohol ions will have easier access to attack the carbon on the melatonin C=O bond. Food safe potassium metabisulfite from the brew store will be used along with NaOH. This will be kept in a closed bottle over a month and TLC will be used to check for changes.

I should have more info in a few weeks. Feedback welcome. Cheers.

There was an american company that sold mexamine as melatonin. I bought a bottle of pills from them, and only when i read the label, i discovered that it wasn't real melatonin. The effects where quite simmilar though.

I've been looking for something like that (and econocial unlike this) with no success. Do you recall the name of the company? Thanks!

I really want to give this to some mushrooms. Or are the mushrooms the ones making me do it?

Anyway, appreciate any leads.

No, i'm sorry. It was more than ten years ago. Must have been somewhere around 2005.

Here is a tested procedure that works with over 90% efficiency.

A solution of 10 g of Melatonin (bought from a Chinese supplier), 7 g of NaOH and 1 g of Sodium Sulfate in 150 ml of isobutanol was refluxed at 107 С for 2 hours under argon (could be substituted with butane lighter gas, or not used if yield is not critical).

After cooling down the RM was washed twice with 100 ml of water. The water was discarded. Isobutanol was distilled off under aspirator vacuum. Dark-brown thick oil was collected.

After a basic workup 7.6 g of gray crystalline Mexamine was collected. Melting point ~117C. Yield - 92.6%. TLC is available but I do not know how to attach it.

Hi There. Good to meet you here, I've read several of your posts when doing Nexus forum
archeological digs

Yep, with butanol there is a clear path. Unfortunately, I can't find it OTC.

I've seen the brown oil form after the solvent evap when using IPA instead of butanol. It smelled "tryptamine". Do you have details on the workup to turn that into crystals (I've heard of dissolving in alcohol, adding some HCl drops, and reducing that by evaporation until crystals start falling out).

Thanks!

Hi,
I did a lot of homework since then.


IPA should work, though reaction time would be longer. Vigorous stirring speeds up the reaction substantially. I used a hotplate/mag stirrer. NaOH tends to clog into a lump.

You can check when the reaction is over by doing TLC. The melatonin spot will disappear completely. The appropriate solvent system is DCM - MeOH (95:5).



I do. Here it is.

1. The oil dissolved in diluted HCl and vacuum filtered. Resulting pH ~3.
2. The mixture is washed with xylene 2x50 ml. Xylene discarded.
3. Basification to pH ~12. After 12 hours grey xtals collected, and washed with a Sodium bicarbonate solution.

You get a much better product if you run these steps twice. The product will be even better if you do Re-x from ethanol. There is no need to do the xylene wash during the 2nd and 3rd cycle.

Fig.1 is the TLC at 1 hour. Pure Melatonin is to the left. To the right is the RM. Some melatonin is still present. It disappeared at 1:45 m.
Fig. 2,3,4 are photos of the product after 1st, 2nd and 3rd Re-x.

Many thanks and gratitude for all the great information Trickster.

Out of curiosity, Have you use ever used Mexamine in a mushroom grow? Did you find any interesting use(s) for it?

Nope.



Yes.

Mexamine is half-way to a more interesting product - 5-MeO-DMT. However, I do not know if it is advisable to discuss it here.

Got it, I believe you are right: this is not the place for synthetic methylation discussion.

We are also looking at getting to 5-MEO-DMT or something similar from Mexamine, but by getting the mushrooms to do the hard methylating work. I think that kind biotransformation discussion is allowed since it simply boils down to getting mushroom material in contact with Mexamine.

Thank you!

What a great thread! Thanks to everyone for the very interesting and useful information.

I am wondering if there any new developments on the topic ?