Author Topic: 5-meo-dmt from melatonin?  (Read 589 times)

rocketman

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5-meo-dmt from melatonin?
« on: August 17, 2009, 05:58:50 AM »
Seeing as phenethylamines are so difficult to synthesize I've started to think about tryptamines...

Anyways, my most recent idea:

React melatonin tablets with hydrochloric acid to give the hydrochloride salt
Filter the slurry to try to extract the melatonin hydrochloride
Add NaOH to neutralize the hydrochloride salt and deacetylate melatonin:
  (n-COCH3 5-methoxy tryptamine + NaOH > Na-CH3COOH + 5-methoxy tryptamine)
Put it in isopropyl alcohol and add 2 moles methyl iodide for every mole 5-methoxy tryptamine
To theoretically make freebase 5-Meo-DMT

Would that theoretically work?

Edit: Also, another thing I can't understand: here (http://www.erowid.org/library/books_online/tihkal/tihkal06.shtml) in tihkal, after reacting methyl iodide with tryptamine he only gets a little dmt with some weird "N,N,N-trimethyltryptammonium iodide". How come? I can't even imagine what that even is.
« Last Edit: August 17, 2009, 07:53:29 AM by rocketman »

Douchermann

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Re: 5-meo-dmt from melatonin?
« Reply #1 on: August 17, 2009, 06:08:19 AM »
I do know that those melatonin tablets contain 2-3mg of melatonin, maybe 10mg in strong ones.  334 tablets of the typical dose would be needed to get just 1g of pure melatonin, (or 100 of the 10mg strong dose).  If you've got no problem buying arse loads of tablets, I say experiment, good sir.  

edit: just saw your edit.  trimethyltryptammonium iodide is the quaternary ammonium salt.  Look that up real quick for a brief definition.  Just put a deficit of electrons on the nitrogen, and a surplus on the extra iodine.  The salt comes from the excess of MeI he uses, and he goes through the typical methods of decomposing this into what he wants.
« Last Edit: August 17, 2009, 06:12:53 AM by Douchermann »

rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #2 on: August 17, 2009, 06:13:47 AM »
Ok, thanks I understand. Hmm. I thought amines could only make salts with acids. Perhaps methyl iodide is acidic enough then. Oh well. It sucks because that first part was easy, anybody could do that at home. But that whole demethylating the salt is long and complicated...

What about if instead of excess MeI you used the right amount of MeI with hydroiodic acid? Wouldn't that put deficits on the nitrogen? I guess not, otherwise he would probably have done that also. Ok well thanks for the quick response I guess this synthesis is not as easy as I thought.
« Last Edit: August 17, 2009, 06:23:16 AM by rocketman »

Douchermann

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Re: 5-meo-dmt from melatonin?
« Reply #3 on: August 17, 2009, 06:22:24 AM »
Haha aye, tryptamine chemistry is actually somewhat harder than phenethylamine chemistry.  Not harder in skill required, per se, but just harder in the reagents required.  Chemicals with an indole structure are far and few between, however, chemicals with 6 carbon ring are quite common.  Welcome to the site, btw. 

rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #4 on: August 17, 2009, 06:26:28 AM »
Well the thing is that the phenethylamines I think are really interesting (2c, doi etc.) they all require chemicals like 2,5,dimethoxy benzaldehyde stuff like that. The only really easy source is like ephedrine or phenylalanine and you can only use that for the simple amphetamines, not so much for the psychedelic ones.

Then again I guess if you know chemistry (which I don't), it's not too hard to synthesize it all from scratch...

Vesp

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Re: 5-meo-dmt from melatonin?
« Reply #5 on: August 17, 2009, 06:26:48 AM »
Quote
Posted by: rocketman      Posted on: Today at 10:58:50 PM
Insert Quote
Seeing as phenethylamines are so difficult to synthesize I've started to think about tryptamines...

Anyways, my most recent idea:

React melatonin tablets with hydrochloric acid to give the hydrochloride salt
Filter the slurry to try to extract the melatonin hydrochloride
Add NaOH to neutralize the hydrochloride salt and deacetylate melatonin:
  (n-COCH3 5-methoxy tryptamine + NaOH > Na-CH3COOH + 5-methoxy tryptamine)
Put it in isopropyl alcohol and add 2 moles methyl iodide for every mole 5-methoxy tryptamine
To theoretically make freebase 5-Meo-DMT

Would that theoretically work?

as he points out, this is probably not super practical. Consider making it from 5-hydroxytryptophan using the oxalic acid, paraformaldehyde method as mentioned in this forum a few places.

There is a bit of information here, Naf1's post probably being the most helpful: http://127.0.0.1/talk/index.php/topic,376.0.html

Also, there is more information here: http://127.0.0.1/talk/index.php/topic,321.0.html

You could easily get 5-OH-DMT from 5-hydroxytryptophan, but I am not entirely sure about how one could methoxylate the hydroxyl in the 5 position.

There is a lot of talk on here about methylating agents though.

Nice to have you on this forum! I hope to see you have success in making this and other compounds. However one thing I noticed that slightly (only slightly!) concerned me is that while I was viewing the members online list, I saw that you had signed up and almost immediately started to post a new topic,  it was only 1:43 minutes apart. Don't forget to search around a bit. ::) It can really help, but it seems like you've been looking other places.

I hope I've given you some ideas,  DMT is probably easier to make then 5-MeO-DMT.

NOTE: While typing this, it appears 3 new posts were posted, so sorry if this has already been covered!
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rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #6 on: August 17, 2009, 06:29:25 AM »
Thanks this is a really sweet forum, I've had lots of stupid ideas about syntheses that are nice to resolve   :)

timecube

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Re: 5-meo-dmt from melatonin?
« Reply #7 on: August 17, 2009, 06:37:19 AM »
Quote from: Vesp
Consider making it from 5-hydroxytryptophan using the oxalic acid, paraformaldehyde method as mentioned in this forum a few places.

After deacetylation of the melatonin, this may work to methylate it the way you want as well.  Not 100% on that though.

rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #8 on: August 17, 2009, 06:42:11 AM »
Yeah thanks timecube well that link (http://www.erowid.org/archive/rhodium/chemistry/tryptamine2dmt.html) in one of your threads would  work instead of the methyl iodide right? I think it also has a way to reduce tryptophan to tryptamine using acetone.
« Last Edit: August 17, 2009, 06:53:32 AM by rocketman »

Vesp

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Re: 5-meo-dmt from melatonin?
« Reply #9 on: August 17, 2009, 06:43:11 AM »
Nope it wont the amino acid part is very important because other wise it will turn into a harmala type alkaloid, a beta-carboline via the Pictet-Spengler reaction. http://en.wikipedia.org/wiki/Pictet-Spengler_reaction

IIRC you can actually buy 5-MeO-Tryptophan as a health supplement however, so you may want to look into that.
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rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #10 on: August 17, 2009, 06:45:04 AM »
Isn't 5-Hydroxy tryptophan (5-htp) the supplement you can buy at health stores? I think then it would be better to go with just tryptophan and make dmt since 5-HO-DMT is reported to be extremely unpleasant.
« Last Edit: August 17, 2009, 06:50:49 AM by rocketman »

Vesp

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Re: 5-meo-dmt from melatonin?
« Reply #11 on: August 17, 2009, 06:52:50 AM »
I think 5-MeO-trypt. is sold as something for health as well as hydroxy-trypt. I am not totally sure though, but it seems like it maybe another sleep aid similiar to melatonin. It probably isn't very popular if it is sold, so I doubt you could find it without ordering it offline.
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timecube

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Re: 5-meo-dmt from melatonin?
« Reply #12 on: August 17, 2009, 07:03:00 AM »
I looked around some and 5-MeO-Tryptophan doesn't seem to be too available, other than in minute quantities in mixtures in some health care pills.

Gross about the Pictet-Spengler occurring rather than the desired effect.  I suppose it may be possible although a bit round about to deacetylate the melatonin, then carboxylate it, then methylate it, then decarboxylate it again.  I'm not sure if the MeO group would interfere with the carboxylation though.

rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #13 on: August 17, 2009, 07:08:59 AM »
If you were to carboxylate it, which position would it carboxylate at?

In any case, I guess this link from the other thread http://www.sciencemadness.org/talk/files.php?pid=86049&aid=2349 is pretty straightforward for methylating it effectively, only requires formaldehyde and oxalic acid which may even be easier to make or obtain than methyl iodide... probably the best bet.
« Last Edit: August 17, 2009, 07:14:37 AM by rocketman »

Vesp

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Re: 5-meo-dmt from melatonin?
« Reply #14 on: August 17, 2009, 07:12:11 AM »
Ah, I was thinking it might be sold in relativly pure form.. that is disappointing.

Carboxylation sounds very impractical to me, and I don't know how you'd go about doing it.
Instead of being sad about the Pictet-Spengler, look at it as a super easy way to MAOI's and with the known DMT synthesis, that is some easy and clean Ayahuasca! (a mixture of harmala alkaloids and DMT like substances, makes you see god and trip for hours vs a few minutes that DMT does alone)

Carboxylation sounds very impractical to me, and I don't know how you'd go about doing it.
Using melatonin in the oxalic acid/paraformaldehyde reaction would likely produce N-methyl-N-acetyl-5-methoxytryptamine. This could then be decarboxylated to 5-MeO-N-Methyltryptamine. You would then just need to add another N-methyl group to get 5-MeO-DMT.
5-MeO-N-Methyltryptamine might be psychoactive in a good way itself.
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timecube

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Re: 5-meo-dmt from melatonin?
« Reply #15 on: August 17, 2009, 07:12:34 AM »
If you were to carboxylate it, which position would it carboxylate at?

Scratch that, I was looking at something wrong.  That won't work because it would want to carboxylate the Nitrogen.

Vesp

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Re: 5-meo-dmt from melatonin?
« Reply #16 on: August 17, 2009, 07:17:15 AM »
http://www.erowid.org/library/books_online/tihkal/tihkal42.shtml This is what would be made with melatonin in the oxalic acid/paraformaldyde reaction after deactylation.

Doesn't seem to be active, but it is a good start to 5-MeO-DMT, isn't it?
here is the wiki as well http://en.wikipedia.org/wiki/5-MeO-NMT
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rocketman

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Re: 5-meo-dmt from melatonin?
« Reply #17 on: August 17, 2009, 07:19:57 AM »
I was just about to point to the tihkal link but decided not to, lol. Yeah, active or not, you're right it's definitely a good start.

What about if you use methyl iodide straight on melatonin to make N-acetyl 5-MeO-NMT, then deacetylate it, and then use methyl iodide again? Would it still make the beta carboline or whatever?

Edit: nevermind I just realized how stupid that idea is. Melatonin has the acetyl at N-1. So it probably wouldn't even make N-acetyl 5-MeO-NMT since the methyl would be at N-2 which I would presume would make it form the betacarboline. Would it?
« Last Edit: August 17, 2009, 07:32:11 AM by rocketman »

timecube

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Re: 5-meo-dmt from melatonin?
« Reply #18 on: August 17, 2009, 07:29:08 AM »
Using melatonin in the oxalic acid/paraformaldehyde reaction would likely produce N-methyl-N-acetyl-5-methoxytryptamine.

I was a little surprised to not find this in Tihkal, as it seems like a natural complement to some of the other compounds with non-symmetric additions to the nitrogen like N-isopropyl-5-methoxy-N-methyl tryptamine.  Most of the asymmetric compounds like this seem to be relatively inactive, and with melatonin also being inactive (for our purposes) he probably rightfully didn't expect much from combinations like N-methyl-N-acetyl.

Vesp

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Re: 5-meo-dmt from melatonin?
« Reply #19 on: August 17, 2009, 07:31:31 AM »
Methyl Iodide is insanely toxic, and I would at least use the oxalic/paraformaldehyde reaction to get to the 5-MeO-NMT compound. It should work for this as the patent says it works for secondary amines..

Methyl Iodide would probably turn 5-MeO-NMT into 5-MeO-DMT, but I am not totally sure, research it and understand how toxic methyl iodide is, MeI is something you seriously don't want to mess with, especially if you have little to no chemistry experience.

A more important question to ask is will 5-MeO-NMT even do a pictet spengler reaction? If secondary amines cannot do a PS reaction, once you have it you can go back to the oxalic/paraformaldehyde reaction.

This is really the most ideal thing too because its not horribly toxic and oxalic acid and paraformaldehyde are both VERY OTC with litte/easy purification required. Also this reaction allows you to use simple labware, which the other reactions such as ones involving MeI (fumehood) will need more complex and expensive labware.


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