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Possible 4-HO-5-MeO-a-MT?

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Weebull

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Possible 5-MeO-N-HO-a-MT?

I saw someone bring up the idea of adding the 4-hydroxy-N structure to the 5-methoxy-alpha-methyltryptamine foundation producing a strangely intriguing idea of hydroxy-methoxy tryptamines... I'm no organic chemist, but would it be at all possible to create a stable(stable enough to survive storage and ingestion) molecule with both a 4-ho and 5-meo structure in it? Possibly bonding the 4-HO to one of the double bonded hydrogen atoms off the methyl group?
 
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What would a 4-Hydroxy-N be? The N indicates a substitution on the amine. A hydroxyl group can not be at the N and at the 4 simultaneously, unless hydroxy groups have figured out all of the secrets to the space-time continual. Now, 5-methoxy-N-hydroxy-AMT could be interesting....many of the N-hydroxy phenethylamines are quite fascinating.
 
Like I said, I don't know organic (or advanced) chemestry, so I apologise for the mistake(s) I made with my wording. With that said, do you think Alexander Shulgin are/have been working on these compounds? Or does anyone know where some information about these be found?
 
It seems like, with Tryptamines, adding a Methylenedioxy ring or making more than one ring-substitution renders the molecule inactive or hardly interesting, at least according to the TiHKAL compounds.

But who know, this one could be different.
 
I'm sure there's good reasoning behind why Shulgin didn't synthesize any of these compounds (4 HO, 5 MeO t's)... maybe they're known to be inactive or are inherently unstable.
 
Interesting... I was just thinking about this the other day, decide to look in here and voila! A thread about this very topic.

It will be interesting to see where this goes.
 
The chemical in the subject is in no way going to be active. Meanwhile 4-OH, 5-MeO -tryptamine could certainly be stable.
 
Trying to get more bang for your buck there weebull? heh. That would be interesting if it had an effect...
 
sorry

sorry but n-oh substituted tryptamines are not active at least not in any realistic dosages, the nitrogen position goes through catabolic reduction and that's why you put methyl groups there because they ere so easily manipulated by your enzymes when on the nitrogen, but the bond is too strong with a a n-oh
at the same time there are alyaws anomolies and if it's never been tasted then you just dont know, that's the beauty of research !
 
sorry but n-oh substituted tryptamines are not active at least not in any realistic dosages
Click to expand...

He's talking about an alpha-methylated tryptamine, and they are active as a primary, not tertiary amine. N-hydroxy AMT & 5-methoxyAMT would be just as active as the non-hydroxylated versions.

I honestly don't know whether 5-methoxy-4-hydroxy AMT would be active, but it seems to have all the requirements for such. It's failing might be the adjacent oxygen atoms - they are easily oxidized to a diketo compound in the same way 1,4-dihydroxy compounds are; on top of the sensitivity of primary amine tryptamines & 4-hydroxytryptamines to oxidation, that's not a good combination for a compound's chemical stability
 
?????

where is there any proof that n-ho-aMT has activity, I'd like to know. and for that matter any n-ho-Tryptamine. just a question I'm not being a smart ass, I am very interested in this subject and want to know more .
 
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