Author Topic: Melatonin to 5-MEO-NET? NiPT? (Read 219 times)

blowjay · « **on:** March 02, 2012, 03:39:23 AM »

Title pretty much says it all, I am sure that this has to have been thought of passively but I can't find very much about the N-x tryptamines let alone the 5-MeO counterparts. Just throwing this half-assed idea out there as it would be very entertaining to be able to turn melatonin into something more interesting.

If nothing else I would enjoy being informed of why melatonin is hard to tweak exactly. Sorry if this is not much of a post but it could give someone a spark.

EDIT: Heh here we go, maybe something could be done to make something along the lines of what is mentioned at the bottom of the TIHKAL entry on NET

"The two geometric isomers, mono-isobutyl and mono-sec-butyl tryptamines are best called NIBT and NSBT. They also have been made by the oxalylamide route and the hydrochloride salts melt at 150-151 °C and 175-177 °C resp. Interestingly, NSBT is one of the two mono-substituted tryptamines that just might have CNS activity. It has shown a generalized and somewhat diffuse intoxication with several studies covering the 25 to 75 milligram range. Short lived, intellectual excitement with some modest sensory enhancements. Promising, and a lot of erotic horniness, but no plus threes, yet.

The tertiary-butyl analogue, NTBT, is the remaining mono-substituted tryptamine that just might have psychotropic potential. In the 5 to 20 milligram area, there is a light-headed intoxication that is a totally pleasant buzz, but nothing more profound than that. Wouldn't it be fascination of it turned out that all of the mono-tryptamines (the NRT's) were GHB-like intoxicants, and totally devoid of psychedelic activity. That would be a true challenge to the SAR crowd. I was told many years ago that NTBT was extremely potent when smoked, but I never received any particulars, and I must leave that as a baseless rumor."

antibody2 · « **Reply #1 on:** March 08, 2012, 11:23:02 PM »

In theory you should be able to reduce the n-acetyl group to an n-ethyl group using LAH. Some one else suggested it a while back but don't know that anyone has bothered to try. That would yeilld 5Meo-NET. It could then be alkylated with formaldehyde and Na(Ac0)3BH to yeild 5Meo-MET, which IMHO would be more likely to be active. Be sure to report back

blowjay · « **Reply #2 on:** March 09, 2012, 10:14:09 AM »

Quote from: antibody2 on March 08, 2012, 11:23:02 PM

In theory you should be able to reduce the n-acetyl group to an n-ethyl group using LAH. Some one else suggested it a while back but don't know that anyone has bothered to try. That would yeilld 5Meo-NET. It could then be alkylated with formaldehyde and Na(Ac0)3BH to yeild 5Meo-MET, which IMHO would be more likely to be active. Be sure to report back

Really?!? This is more than what I had hoped to possibly hear. I have just become interested in 5-MeO-MET recently as well and this sounds much more promising than what I had suggested with the longer chains. If this can be a possibility that would be quite something considering how much melatonin goes for.

Thank you for your input, bulk melatonin powder goes for very little and if this could go another way without the LAH using more safe and available means I am all ears.

atara · « **Reply #3 on:** March 11, 2012, 12:29:47 AM »

Honestly, I think the reason this route doesn't get a whole lot of attention is that it's just a damn pain to reduce an amide, whereas it's far easier to perform basic hydrolysis of melatonin to mexamine:

http://its.goofyti.me/u/http://www.erowid.org/archive/rhodium/chemistry/mexamine.html

Acidic hydrolysis of melatonin is definitely not recommended due to the cyclization to a beta-carboline: simply put, when an amide is acid-hydrolyzed, it is first protonated; this protonated amide is in equilibrium with an iminium which easily alkylates indole at C2.

However, if you have some LAH lying around, it's fine. Otherwise, your options for reducing an amide are:

catalytic hydrogenation, which is hard,

the combination of borohydride salts and Lewis acids (such as zinc, lithium, or phosphoryl chloride), which suffers the same problem as acidic hydrolysis of melatonin,

Red-Al, which is just as hard to get as LAH, though safer to handle and use,

Silyl hydrides, which you don't have,

Diborane, which, no, bad idea.

So for most practical purposes it is better to hydrolyze melatonin. The reason melatonin is hard to work with is the cyclization noted above, as well as that it is very susceptible to oxidation, which is why the hydrolysis was performed under N2.

Interesting possibilities to me are 5-MeO-EiPT and 5-MeO-AiPT (allyl-isopropyl), which are both unknown and possibly good.

antibody2 · « **Reply #4 on:** March 18, 2012, 06:57:53 PM »

Not sure if zinc borohydride will work or not.

Some effort has gone into reducing a 2° amide with zinc borohydride, but the product isn't NMT(although it has TLC rf similar to NMT), so it is possible that the zinc borohydride is hyroborating the indole double bond. Also attempts to react this "not" NMT product with methyl formate to form a 3° amide fail (even after one week reaction times! where as the 2° amide is formed in a few hours), so whatever this product is, it is considerably less reactive than a 2° amine.

This is using a large XS of borohydride (2X), perhaps with stoichiometric amounts of hydride the results will differ.

I think Diborane will also hydroborate the indole double bond, there was a discussion on the topic some time ago.

Tsathoggua · « **Reply #5 on:** March 19, 2012, 05:55:11 AM »

Just avoid making 5-MeO-DET. This one was described in TIHKAL and on erowid as quite unpleasant.

Why not say, react melatonin with an alkyl halide, to produce a mixed amide/amine, then reduction of the amide to the ethylamine using LAH to give the desired product.

There is always the option of cleaving the ether with HBr to give a 5-hydroxylated product, to produce bufotenine analogs. Although bufotenine is hard on the body. Toady has tried the latter, and it does produce quite some pressor type effects, rapid heart rate and a general feeling of 'shit, that felt like a punch in the gut'

One could always halogenate the ring though, and use any of the known methods for removing an aromatic halide.

atara · « **Reply #6 on:** March 20, 2012, 04:09:25 AM »

N-alkylation of amides (among other things) with alkyl halides via KOH in DMSO:

http://www.sciencedirect.com/science/article/pii/0040402079870350

This is certainly an easy way to make asymmetric weird things like 5-MeO-MET...

blowjay · « **Reply #7 on:** March 21, 2012, 07:03:23 PM »

I can't find the text but if it requires KOH and DMSO then we are certainly on the right track towards something more OTC friendly.

myCH3 · « **Reply #8 on:** March 22, 2012, 02:13:22 PM »

Quote from: atara on March 20, 2012, 04:09:25 AM

N-alkylation of amides (among other things) with alkyl halides via KOH in DMSO:

http://www.sciencedirect.com/science/article/pii/0040402079870350

This is certainly an easy way to make asymmetric weird things like 5-MeO-MET...

if the asymmetric ones are easy 5-meo-mipt is quite nice in my opinion

blowjay · « **Reply #9 on:** March 24, 2012, 01:04:29 AM »

Would 5-MeO-MPT (not the isopropyl, just good ol propyl) be a possibility or would it be too had to keep it as just a straight chain propyl?

Author Topic: Melatonin to 5-MEO-NET? NiPT? (Read 219 times)

blowjay

Melatonin to 5-MEO-NET? NiPT?

antibody2

Re: Melatonin to 5-MEO-NET? NiPT?

blowjay

Re: Melatonin to 5-MEO-NET? NiPT?

atara

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antibody2

Re: Melatonin to 5-MEO-NET? NiPT?

Tsathoggua

Re: Melatonin to 5-MEO-NET? NiPT?

atara

Re: Melatonin to 5-MEO-NET? NiPT?

blowjay

Re: Melatonin to 5-MEO-NET? NiPT?

myCH3

Re: Melatonin to 5-MEO-NET? NiPT?

blowjay

Re: Melatonin to 5-MEO-NET? NiPT?