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Author: Subject: 5-MeO-DIPT Synthesis from melatonin
AqueousLayer
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[*] posted on 18-12-2016 at 04:14
5-MeO-DIPT Synthesis from melatonin


5-MeO-DIPT: https://erowid.org/library/books_online/tihkal/tihkal37.shtm...

Here's what I thought about :
1. The amide is turned into a primary amine by NaOH, which is then neutralized.

2. The amine is alkylised by 2eq of 2-chloropropane.

What would be the condition of these reactions?

Step 1 requires heating in reflux for several hours. The only example I could find stated 16h at 100-110C, which seems like a lot of time. I also don't know how hot the solution can be without destroying the melatonin.

2-chloropropane boils at 36C, so the solution would have to be cooler than that for step 2.
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stoichiometric_steve
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[*] posted on 18-12-2016 at 05:52


Quote: Originally posted by AqueousLayer  
5-MeO-DIPT: https://erowid.org/library/books_online/tihkal/tihkal37.shtm...

Here's what I thought about


You didn't bother thinking about doing any literature research at all, did you?
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AqueousLayer
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[*] posted on 18-12-2016 at 05:57


The reaction isn't exactly the same and could be optimized for this particular synthesis. I did as much research as I could with the given means.
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Ozone
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[*] posted on 18-12-2016 at 07:33


The synthetic route is straight-forward and has been elucidated, in detail, elsewhere.

Barring a discussion of interesting novel Chemistry, many of us will not provide assistance in the preparation of a drug that is schedule 1 or forbidden just about everywhere (US since 2003, officially in 2004).

Aside, I would personally be disgusted if I had to sign an invasive waiver in order to buy a bottle of melatonin (which is a great help with my insomnia) because a bunch of fools were using it to produce a relatively crummy psychadelic.

Case in point: I can no longer easily buy Sudafed (the *only* OTC drug I can buy that actually works for the sinus congestion and headaches I get without untoward side effects... like insomnia), because a bunch of fools used the pseudoephedrine it contains to make methamphetamine.

Best of luck to you,

O3

[Edited on 18-12-2016 by Ozone]




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[*] posted on 18-12-2016 at 08:38


Quote: Originally posted by AqueousLayer  
I did as much research as I could with the given means.


A quick look at Rhodium is all you could do?

http://www.sciencemadness.org/madscifaq.html#2.1_Board_topic...

Let's stick this in beginnings, then. In keeping with site policy, it is OK to ask questions about ANY type of chemistry.




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18-12-2016 at 08:38
zed
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[*] posted on 26-12-2016 at 19:36


Destroy Melatonin?

Well maybe.

Indoles may, or may not, be fussy, depending on exact conditions.

A few years of reading on the subject, may clarify.

Processes that start with tryptophols are sometimes more favored by big pharma.

https://www.google.com/search?q=sumatryptan+synthesis&ie...

Might be beyond you at this point. But, there are several interesting articles therein.





[Edited on 27-12-2016 by zed]
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Rich_Insane
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[*] posted on 28-12-2016 at 23:38


You'd need a base like N,N-diisopropylethylamine or triethylamine to prevent formation of the quaternary amine. This is mentioned in the TIHKaL reference you cited. It looks like the synthesis of the product, 5-MeO-DIPT is pretty well documented in the literature, so that's your best bet.

Here's a link referring to the hydrolysis of melatonin from Rhodium: Hydrolysis of Melatonin

Sodium dithionite is probably used to prevent oxidation of the product. Otherwise the reaction is a simple hydrolysis.
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laserlisa
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[*] posted on 29-12-2016 at 09:50


Quote: Originally posted by Rich_Insane  
You'd need a base like N,N-diisopropylethylamine or triethylamine to prevent formation of the quaternary amine. This is mentioned in the TIHKaL reference you cited. It looks like the synthesis of the product, 5-MeO-DIPT is pretty well documented in the literature, so that's your best bet.
...

The role of the base is not to prevent overalkylation, its just a non-nuclephilic base that mops up protons without getting alkylated itself afaik.
Also there is no risk of overalkylation to the quartinary amine in this case because of the bulky isopropyl groups.
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[*] posted on 3-1-2017 at 18:28


As I recall, Shulgin used hydrogenation of the Acetone Imine/Enamine to produce some Di-isopropyl Tryptamines. Steric hindrance was such, that alkylation of the mono-isopropyl tryptamine, via isopropyl-chloride....didn't work very well.

Though I am having trouble finding the reference.

Well, maybe I'm just wrong. Can't find it.

[Edited on 4-1-2017 by zed]
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