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

rocketman · « **Reply #20 on:** August 17, 2009, 07:34:36 AM »

No, you're right that paraformaldehyde/oxalic acid is definitely going to be less complicated than that whole NMT beta carboline etc. I guess that's the plan to stick with for methylating tryptamine or 5-methoxy tryptamine. Easier to get too probably I had no idea where the iodomethane would come from anyways.

timecube · « **Reply #21 on:** August 17, 2009, 07:37:48 AM »

The MeI method should be doable as in Shulgin's DMT synthesis, but like you said nowhere near as practical.

Vesp · « **Reply #22 on:** August 17, 2009, 07:41:56 AM »

Naturally you'd have to make the MeI from HI and MeOH. HI, and I2 (often a precursor for HI, using H2S) are both watched and regulated substances. Wouldn't surprise me if MeI were as well regulated.

Oxalic acid and paraformaldehyde can be bought at stores often as a cleaner or for some camping supply. This should help you out when it comes to getting' the chemicals
http://127.0.0.1/Douchermann/otcdatabase.html

rocketman · « **Reply #23 on:** August 17, 2009, 07:50:03 AM »

Really nice database. Yeah this synthesis is definitely doable. I'll tell you how it works if I try it.

zzhuchila_clocker · « **Reply #24 on:** August 17, 2009, 08:19:01 AM »

I don't know concerning oxylic acid/formaldehyde, but eshweiler-clark methylation (CH2O + HCOOH), is not applicable to tryptamines as it would produce a carboline derivative(-CH2- making a cycle between tryptmine nitrogen and position 2 of indole). That i have read on some drug forum, not though sure about that..

Vesp · « **Reply #25 on:** August 17, 2009, 08:26:40 AM »

Please read the patent as posted in one of the links I've provided.
The oxalic acid is turned into formic acid when it is heated at 100*C for long periods of time.

Would the beta-carbonlines form with the 5-MeO-NMT? After looking around a bit, I think they probably would unfortunately, but I am hopeful, and unsure.

That is why tryptophan, not tryptamine is used. The COOH prevents the pictet spengler reaction.

rocketman · « **Reply #26 on:** August 17, 2009, 08:29:13 AM »

Yeah tryptophan's carboxyl group would prevent the beta carboline from forming as it's in the R-a position. But wait would it still form a-COOH NMT or a-COOH DMT then?

timecube · « **Reply #27 on:** August 17, 2009, 08:38:11 AM »

I looked around some and 5-hydroxytryptophan is available in somewhat usable quantities, but no where near as cheaply as regular tryptophan.

rocketman · « **Reply #28 on:** August 17, 2009, 08:40:45 AM »

Well the thing is that the only 5-hydroxy psychedelic really known, butofenin, is supposed to be extremely unpleasant. I guess you could reduce the hydroxy group somehow but then you might as well start with tryptophan.

Vesp · « **Reply #29 on:** August 17, 2009, 08:44:42 AM »

Quote

Yeah tryptophan's carboxyl group would prevent the beta carboline from forming as it's in the R-a position. But wait would it still form a-COOH NMT or a-COOH DMT then?

Read the links I have given you rocketman. I've already answered your question in this thread. Read it over again, and read my links, and the links on other threads I've linked too..

rocketman · « **Reply #30 on:** August 17, 2009, 08:52:18 AM »

Yeah ok I just found it on the patent. From what I see on page 464 I guess it does methylates all the positions it can. So tryptophan would make a-carboxyl dmt which can be decarboxylated to dmt. A good plan.

And melatonin is a bad choice after all since it would only give you 5-meo-nmt in the end./

Vesp · « **Reply #31 on:** August 17, 2009, 08:53:36 AM »

As I've stated earlier, and have given 2 links to on this forum that have also stated it.

rocketman · « **Reply #32 on:** August 17, 2009, 08:55:29 AM »

Interesting, I was just thinking... after methylating tryptophan you would make a-carboxyl n,n, dimethyl tryptamine, right? and then you'd have to decarboxylate it.

But you could skip the whole methylation and just reduce the carboxyl on the tryptophan to get AMT. I mean it's not DMT but it's still a psychedelic.

timecube · « **Reply #33 on:** August 17, 2009, 09:00:23 AM »

Do any of you have the link to the Copper (II) acetate synthesis from copper sulfate.. I thought it was at designer-drug but am having trouble finding it.

I remember the first time I found it, it was kind of buried in the google search. I think the word "synthesis" doesnt actually appear on the page which makes it harder to find.

Going through the copper chelate seems like the simplest route from tryptophans to tryptamines.

rocketman · « **Reply #34 on:** August 17, 2009, 09:15:13 AM »

Is this what you're looking for? I found it on wikipedia.
CuSO4.5H2O + 4 NH3 + 4 CH3COOH ? Cu2(OAc)4(H2O)2 + 2 [NH4]2[SO4] + 8 H2O

Although I think any acetate salt would do.

Vesp · « **Reply #35 on:** August 17, 2009, 09:20:34 AM »

This is unlocked for now, just please go over the references.

The amide of melatonin would actually hydrolyze and then allow for the Pictet-Spengler reaction reaction to happen so this method using the oxalic/paraformaldehyde will not work on that actually. I had a different structure in my mind. I don't know what I was thinking

zzhuchila_clocker · « **Reply #36 on:** August 17, 2009, 07:59:52 PM »

I checked thoroughly through links and a patent for methylation of amines with oxalic acid and paraformaldehyde, and did not find any confirmation about tryptophan can be methylated to N,N-dimethylTrp, avoiding Pictet-Spengler cyclization. The only mention were Naf1's words in another thread that DMT can be obviously produced by Trp dimethylation with (COOH)2 and CH2O followed by decarboxylation via cyclohexenone-catalysed decarboxylation. He might be unaware of Pictet-Spengler reaction, and that might be just a proposal (fair for most amines btw, but not tryptamines). If there is still a refference on that, i would like to see it. Seems very unlikely, but very promising. I'll send Naf1 a PM.

Quote

Using melatonin in the oxalic acid/paraformaldehyde reaction would likely produce N-methyl-N-acetyl-5-methoxytryptamine.

Amides are known not to be methylated in usual Eshwailer-Clarke reaction, becuse amide nitrogen is inactivated by Ac, partually becoming a tautomer R'-(+)HN=C(O-)R and losing its electron pair. I checked in the patent for oxalic acid usage, and there were no mentions of amides can be methylated. I think, if that was the case, autors would surely have claimed it as a revolutional method for amides methylation in Eschwailer-Clarke type reaction, and if they did not, that means it does not work on amides, neither on melatonin

rocketman · « **Reply #37 on:** August 17, 2009, 09:15:02 PM »

Although I just remembered. You can deacetylate melatonin to give 5-methoxy tryptamine using NaOH, right? That's what Shulgin used for a starting material for 5-meo-Dipt. http://www.erowid.org/library/books_online/tihkal/tihkal37.shtml. So I guess it's just trying to methylate the nitrogen which gives the betacarboline.

As for tryptophan I think it would be simplest just to try AMT given that it's simply tryptophan with the R-COOH reduced to R-CH3 (although AMT is probably a poorer drug than DMT). Or then again you could decarboxylate it to tryptamine and make DET or DIPT or something, also without the beta-carboline forming. Not DMT but still nice.

timecube · « **Reply #38 on:** August 19, 2009, 12:45:56 AM »

Quote from: zz-zhuchila on August 17, 2009, 07:59:52 PM

I checked thoroughly through links and a patent for methylation of amines with oxalic acid and paraformaldehyde, and did not find any confirmation about tryptophan can be methylated to N,N-dimethylTrp, avoiding Pictet-Spengler cyclization.

The more references I go through, the more it seems that tryptophan is a prime candidate for Pictet-Spengler cyclization, and that nothing attached at the alpha position seems to really change this.

Edit: Hopefully this goes to the correct page when you open the link in your browser. Scroll down a bit to section 3.4 and there is an example of tryptophan undergoing cyclization.

http://books.google.com/books?id=hLYgFxCuQNoC&pg=PA475&lpg=PA475&dq=%22Pictet-Spengler%22+%2Btryptophan&source=bl&ots=lwsyGERwpD&sig=Mf070E1UFw9Zvlc4G2G7vSYqQTs&hl=en&ei=i0OLSrujFc6wmAfT7ci1DQ&sa=X&oi=book_result&ct=result&resnum=1#v=onepage&q=%22Pictet-Spengler%22%20%2Btryptophan&f=false

Vesp · « **Reply #39 on:** August 19, 2009, 01:05:19 AM »

Yeah, I'd be interesting in seeing some!

I found this..

Quote

Tryptophans: Diastereocontrolled reaction
The reaction of enantiopure tryptophan or its short-chain alkylesters leads to 1,2,3,4-tetrahydro-?-carbolines in which a new chiral center at C-1 adopts either a cis or trans configuration towards the C-3 carboxyl group. The cis conduction is kinetically controlled, i.e. it is performed at lower temperatures. At higher temperatures the reaction becomes reversible and usually favours racemisation. 1,3-trans dominated products can be obtained with Nb-benzylated tryptophans, which are accessible by reductive amination. The benzyl group can be removed hydrogenolytically afterwards. As a rough rule, 13C NMR signals for C1 and C3 are downfield shifted in cis products relative to trans products (see steric compression effect).[6][14]

-- http://en.wikipedia.org/wiki/Pictet%E2%80%93Spengler_reaction#Asymmetric_Pictet-Spengler_reaction

Wiki's sources are: http://pubs.acs.org/doi/abs/10.1021/cr00038a004
http://pubs.acs.org/doi/abs/10.1021/ja00543a012

Yeah, you maybe right, I didn't read it all the way so I don't know.

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

rocketman

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timecube

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Vesp

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rocketman

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zzhuchila_clocker

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Vesp

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rocketman

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timecube

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rocketman

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Vesp

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rocketman

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Vesp

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rocketman

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timecube

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rocketman

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Vesp

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zzhuchila_clocker

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rocketman

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timecube

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Vesp

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