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pyridinylethylamine

(zonk)

(zonk)

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Joined
May 24, 2008
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687
Looks to me like a somewhere between tryptamine and phenethylamine but closer to PEA i guess. Only info i got was that it's a possible H-1 agonist/ antagonist and slight cardiac stimulant due to possibly releasing catecholamines. Is this base structure worth exploring as a new phenethylamine or tryptamine analog class? Or would the tryptamine analogs be pyridinylpropylamines?
 
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I have heard a 3rd hand report of people buying 4-pyridine methyl acetone being used seemingly without users noticing. The more nucleophilic the 4-position, the better but what the lone-pair does, I don't know. 1-(pyridin-4-yl)propan-2-one CAS: 6304-16-1 Ia known as is the amphetamine - but no papers and I suspect metabolism could be BAD. A dead end.
 
I would venture and say it's similar to other cathinone based drugs like pvp. Not worth it IMHO.
 
Those lone-pairs will give an interesting result. No p-OH can be formed so oxidation of the alphamethyl group although the compound will be less lipophilic. Compare pyrazolam - exit's body unmetabolized. The -N= prevents the liver enzymes from breaking it down and in spite of it's lower cLogP, 0.5-1.0mg does help anxiety while having little abuse potential. The nitro proved to have potent anti-depressant action (to bridge presentation to SSRIs working) while the ethynly is like all the good stuff in alcohol without the dark corners (NMDA obviously makes people violent). So ideal for alcohol detox. So all 3 have commercial use, but I can't afford to patent them. The synthesis is the patentable as are the confirmed (in rodent model) actions of the other 2. Same thing, not metabolized. That scaffold with EWGs, EDGs & just steric bulk (2-trifluoroethyl was interesting as a hypnotic that, again, had much less abuse potential. First into man....
 
Sorry for the off-topic question but was pyrazolam found to help as AD only after a while of building a blood level and changing serotonergic function like SSRI's (and this wouldn't happen to be published wouldnt it? Is pyrazolam being investigated for legit use?), or are the effects pretty rapid and if so wouldn't that be more of a general SRI effect?

Wasnt really expecting pyridinyl compounds to be inherently toxic via metabolism considering things like niacin and nicotinamide (however there its 3-subbed), dont know about isonicotinamide its hard to find.
 
Is there any chance of this being a nicotinic ACh agonist?

Does remind me a bit of a decyclized primary amine homolog of nicotine, minus the stereocenter, and with the sidechain relocated to the 3 rather than 4 position. And even more so of betahistine, a H3 antagonist, thats just a relocation of sidechain from 2 to 3, and an N-methyl away.

31
 
I feel that this thread deserves structures.

1-(3-pyridinyl)-2-methylaminopropane.png
 
3-(dimethylaminoethyl)-7-azaindole.png


Those are just two underexplored pyridinyl molecules. There are more.
 
4-azatryptamine instead of 7-aza would be an excellent idea since the aza would be providing the 4-position polarity somewhat a la psilocin - promising? Other than that they are not bioisosteric to their tryptamine counterparts.
 
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