5-MeO-Tryptamine Synthesis From Melatonin

[Osmosis Vanderwaal]

Someone should go that extra step and add a dimethylation before or in lieu of the acidification for

5-meo-dmt....(?)

 

[HerrHaber]

In the first step, hydrolysis of acetyl group (N-deprotection) can be done both with acid either base (which I would go for), but this is probably not what you meant by acidification and it yields the primary amine (R-NH2) mexamine that can be further dialkilated (dimethyl is just a popular choice amongst many) and by preparative common sense the easy method of isolation and purification of the N,N-dialkyl-5-MeO-triptamine is by forming the hydrochloride salt with HCl therefore obtaining a stable white (in case of mexamine hydrochloride) solid substance instead of the brownish solid you'd better store in the freezer freebase.

 

[Osmosis Vanderwaal]

I meant 5-meo-dmt, and that was my natural thought because it is smokable in that form and it is a natural form, occuring in plants and the secretion of Colorado river toads.vit is also easily prepared via dimethylation if the monamine the terminal position of the ethane moiety. It has a lot of demonstrated beneficial effects not demonstrated in the dialkyl variety and 30 mg dosage for a breakthrough experience

 

[SonOfJessieBerg]

all these materials are legally available for me to buy. ive read through comments and seen that its not active and is a precursor for other 5meo chems. Will it be easy to make 5 meo mipt, its the only chem im interested in tryptamines. dipt would work too.

 

[HerrHaber]

Well melatonin is available in bulk quantities for a relatively low price and melamine is easy to obtain from it in decent yields, 5-MeO-trypamine is also sold by some here on this forum (check the listings). From comercial mexamine (5-MeO-tryptamine) is better since it may be expectable to have a greater purity. The alkylation reaction is conventionally done with formaldehyde and STAB (Na triacetoxy borohydride), yields are better if you use formaldehyde bisulphite addition compound but simple will also do, as well as NaBH4 instead of STAB. 1,2-dichloroethane seems to be the solvent of choice for one reason or another. Cheers!

 

[HerrHaber]

Symmetrical products are easier to prepare, such as DMT, DET, DPT and DIPT that has curious effects on the diisopropyl tryptamine (without 5MeO) the effects are 100%auditory. 5-MeO-MIPT is cool but trickier to make also from mexamine.

 

[SonOfJessieBerg]

thank you so much for the reply. Im actually new to all this and ive read extensively about the chemicals i can prepare via legal route. 5-meo-tryptamine is the only precursor i can make because all the reagents and chemicals required for it are legal in my country and pretty cheap except melatonin. The rest chems i need atleast 1 illegal precursor. So i choose 5-meo for now. I have a question - Ive done basic DMT extraction from MHRB i know this is very easy compared to synthesis of chems being discussed here, but im a good instructions follower. Do you think as a complete newbie i can follow instructions and synthesize 5 meo mipt or atleast any of the chems other then mipt. ? this is purely based on my curiosity and i have no intention to scale up and sell. And i really do not want to buy grey legal chems from outside. though we dont have any analogue act i still dont want to risk ordering tryptamine precursor. in 100$ i can get all the chemicals mentioned in this post. and another 100$ on glassware im good to go. what do you suggest?

 

[SonOfJessieBerg]

do you mean that i can prepare DMT,DET,DPT with tryptamine precursor and is easier then 5-meo-mipt from tryptamine precursor? sorry for stupid question im new here and trying to learn as much as possible with all the chemical terminologies.

 

[HerrHaber]

From melatonin you can get 5MeODMT, 5MeODET, and só on. For simple ones like DMT, DET and só on you start from tryptamine.

 

[SonOfJessieBerg]

would it be easy to make mipt from tryptamine? If i follow instructions correctly? Or is it more complicated then the instructions given

 

[HerrHaber]

Good question, the alkylation of nitrogen occurs via the temporary formation of an imine (double bonded carbon with nitrogen) which is reduced by STAB which is the most selective for imine reductions. If you want the both substituem-nos of the nitrogen to be identical it is much simpler by adding stoechiometric amount of say, formaldehyde for methyl. For mipt you must treat the tryptamine (with or without MeO on 5) I guess first with acetone then reduce to RHN-iPr the imine followed by treatment with formaldehyde and reduced. Alkyl halides are notorious to form the halogen quaternary ammonium salt, so MeI is excluded. Another agent is dimethyl sulfate but this is seriously dangerous. Acetone imine then reduction followed by treatment with Me2SO4 the way I see it.

 

[HerrHaber]

It also may be likely that melatonin hydrolysis would be simpler and more high yielding than decarboxylation of tryptophan. There is also a gap in price... regarding tryptophan you should know that LD (racêmic) is as good as the optically pure L-Trp just in case it’s cheaper. I’ve seen melatonin super affordable up to kilo quantities, if you buy like quarter of a kilo or more ... 15-25g I would also appreciate. I have like 5g and I should hydrolyze it, I had success with methanolic KOH.

 

[SonOfJessieBerg]

really appreciate your detailed answer. Ive checked a thread where the user has succesfully made mipt. Should you think i should try it ? im a totally newbie i can follow instructions well. whats your thought on a total newbie synthesizing tryptamine and then mipt from it?

 

[SonOfJessieBerg]

it cots me 200$ for a kg of melatonin in my country. but for 20$ i can get 100G melatonin. the rest of the chemicals are under 10$

 

[SonOfJessieBerg]

also im not at all looking to scale up and sell this. this is purely based on my curiosity to try making this substance and only for personal consumption. so even if i have 2G of each chemical im more then happy! haha

 

[HerrHaber]

I am glad you aren’t thinking about financial benefit when you do Chemistry. The feeling you get when taking something you made yourself or got from someone whom you thought the preparative dark arts. In this moment I am enjoying some D-amp from a mate who got to be a chemical engineer from my suggestion. Your price for melatonin is very good, I wish I could get it at such a low price but then again I only have a small part of my former lab and some crucial items missing must be bought. I worked with tryptamine both at my home lab and in academic setting and I recommend doing at least two symmetrical products dimehyjl and diisopropyl then you may know your way to make mipt. As your melatonin is so affordable I see no point in practicing with unsubstituted tryptamine. Be careful with consuming or accidentally interact with 5MeO’s they are potent and preferred to be taken willingly in a proper moment. I did the hydrolysis of melatonin and some accident led me to the discovery of a nice way to purify it well, but that notebook is lost.

 

[SonOfJessieBerg]

cant wait to start the journey. chemicals are cheap here but i dont have experience buying them so i have to research a lot before buying. Ill definitely try out the easier substances first which you mentioned. Yea those 5 meo are active in mg. ill be sure to be careful. thank you for the help

 

[Brinda]

Great synthesis

 

[Rabidreject]

I’m in basically the same situation as the OP only iv tried the ketone catalysis oof tryptophan to tryptamine using cyclohexanone.
Iv tried it three times according to the rhodium literature and two of the times the tryptophan didn’t even dissolve, it all just turned dark (the solvent) brown and the goop (which I assume was unconverted tryptophan) was yellow.
On the second run I thought fuck it and added a lot more cyclohexanone and it dissolved the tryptophan.
I then mixed it with DCM or methylene chloride and now I need to buy some baking soda or bicarbonate of soda to wash it.
I’ll then observe what happens - I may need to put it in the freezer to crash out the tryptamine - if there actually is any in there!
With regards to the yellow goo, iv done the same. I’m extracting it with DCM and then I’ll wash it - the thing that puts me off is that it never stopped being a powder on the bottom of the flask. It did release a load of bubbles but it does that when it refluxes anyway
I would say - also as a complete beginner, this is a pretty hard reaction to get right.
iv also tried the peppermint or spearmint conversion method with no success.
Tbh, I’m now just thinking of using the cyclohexanone for another reaction with a certain substance extracted and made from pepper. I was surprised how easy it looks tbh.
I wish someone would just write out the syntheses correctly (unless it’s just me).
I need to study TLC a little more - I have the silica plates and the tiny little glass tubes for it.
I think YouTube is needed to purify the black pepper extract, that I have, to piperine and then to piperidine.
from there, I KNOW cyclohexanone can be extremely useful for the production of PCC.
again, I’m not looking to scale up or sell - those days are long gone. I did my stretch for selling and now I stay to myself.
I figure even if I can convert a gram of tryptophan to tryptamine - to me, it’s worth it.
I have basically given myself a year to produce DMT, DET, DPT instead of simply extracting the root bark, if I can figure it out I could make enough DMT for myself for life…

 

[HerrHaber]

You may have not noticed that cyclohexanone is a carbonyl and in anhydrous conditions ready to react with amine to form the cyclohexyl imine, it might be just less applicable in this particular case. I had been reading tihkal for years before figuring out that oxalyl chloride can react with two molar equivalents of indole and permanently mess up that batch. I knew as a fact that tryptamines need more experience and careful workup details such as lab temperature, ambient moisture and inert gas. It is true that LAH is outdated and one should get stuff like Red-Al for safely reducing the indol-3-yl glyoxylamides to tryptamines without a fire hazard.