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NBOMe Tryptamines

Solipsis

Solipsis

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There is already the 5-MeO-DMT analogue called 5-MeO-NBOMe, which you can see here: http://isomerdesign.com/PiHKAL/explore.php?domain=tk&id=5505

It has an affinity for 5HT2A of 1.49 nM which is not great but not very bad either I gather.

So what about the N,N-DMT analogue that may be called NBOMe-NMT (N,N-MBOMe-T sounds complicated :) ), I don't care about the name really...

It would probably be less potent, but I would be interested to know if there is any reason to believe this would be worth trying?
Are any of these?

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Solipsis said:
So what about the N,N-DMT analogue that may be called NBOMe-NMT (N,N-MBOMe-T sounds complicated :) ), I don't care about the name really...
Click to expand...
The "T" refers to "tryptamine", which is 3-(2-aminoethyl)indole. The structure above is 3-(aminomethyl)indole.

Anyway, the compound was already published a long time ago. See the czechoslovakian (!) patent CS 105955 from 1962, available for free online (http://www.upv.cz/en.html). I hope you speak Czech though...

After OCR and an online translation of the patent one can read that the compound in question has hypotensive and slightly sedative effects (dosage not given though). Duration is said to be "short". I'd appreciate if some native Czech speaker could check this info.
 
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You are so right. I suck, this was done much too hastily...
So there, I fixed it. Thanks for the article, I can throw it through a translator. :D
(This is where you would say: good luck, what with all the jargon)

Unfortunately the pdf is in image not text. I can't imagine OCRing this with all the
noise but alrighty then.
 
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Yeah, I'd been aware of their high affinity for some time. The problem again is the elimination of the secondary amine quickly through first pass metabolism, as with the phenethylamine derivatives. Maybe there is so activity nasally/rectally/sublingually/IM/IV. Of course, this is an easy one to make even for someone at home... But that's enough about that, I suppose.
 
I think it looks like a great idea, although I wonder why Nichols would not have tossed a few of these analogs into his published NBOMe work already... as far as I know there is no reason not to at least make one or two just for comparative sakes considering how many phenethylamine derivatives his group did (unless he did and I just don't remember the publication that well).
 
Hyperthesis said:
I'd appreciate if some native Czech speaker could check this info.
Click to expand...
Yep that's what it says. Calming, mildly sedating effects and long-term hypotensive effect. Then there's just synth info.

I won't mind translating the whole text if you need to but I cant cope with english chemistry nomenclature etc. :p
 
nuke said:
Yeah, I'd been aware of their high affinity for some time. The problem again is the elimination of the secondary amine quickly through first pass metabolism
Click to expand...

Some of the secondary amines are active, there are two published reports of baeocystin showing activity in the same dosage range as psilocin and all the isomers of N-butyl tryptamine show activity as well. Not to mention NMT, though it seems unimpressive Shulgin wrote "smoking of 50–100 mg gave visuals that lasted for maybe 15 seconds."
 
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The NBOMe tryptamines were tested by Erny's group and found to be inactive. If you look at the PhD theses by Ralf Heim and Maria Silva these compounds have fairly low efficacy at 5HT2A despite their high binding affinity, and are very weak partial agonists at best. Think DOBU.

Indeed N-(4-bromobenzyl)-5-MeO-tryptamine was briefly sold as an RC a few years back after its very high binding affinity was published, but was quickly retired from the market after it turned out to be a potent and selective 5HT2A antagonist rather than an agonist!
 
This is all very interesting, thanks. Even if it doesn't really result in something worthy of bioassays.
Do you think these compounds are simply too large? Also I would be interested to hear more about some basic SAR info about agonism and antagonism or are we really bad a predicting that at this point?
 
Current thinking is that the psychedelic tryptamines bind to 5HT2A in a different conformation to the phenethylamines, so the SAR are not directly comparable. Same as how THC binds to CB1 in a different conformation from WIN 55212-2 etc, same target but different binding modes, not necessarily even the same amino acids being bound to in the active site.
 
Wonder if there's a way to make that Tryptamine with a hydroxyl group in the 4 position. Seems like the magic lies predominantly in the 4/5 position for tryptamines.
 
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