Cyclized "Tryptamines"

[Morninggloryseed]

I have read here, and elsewhere that these two are active.

Anyone know of any citations that prove human activity, or at least animal/test-ube activity that would suggest psychedelic activity?

The first is obviously a derivative of 5-MeO-DMT and the second from a-MT. The second is most appealing in that it is a hybrid between a PEA and a tryptamine. Also, it is the lower half of LSD.

Thank you.

 

[Phanerothyme]

That second compound is really interesting. I don't know enough to know if it would be active in humans, or even safe for that matter, but I would love to hear from someone who does know.

 

[vecktor]

compound 2 the benzcdindole:
for related N alkyl substituted benzcdindoles

J. Med Chem 1988, 31 1746-1753

that paper will link back to other work by Nicholas Bach and others at Lilly in the mid eighties

they are it seems fairly selective 5-HT 1 (whatever) agonists and also D2 agonists which inhibit prolactin release.
there is no proper data that I can find on the unsubstituted coupound 2, most of those looked at were N-n-propyl or N methyl.

neither of these two are active psychedelics afaik , the first is an artifact and people wh replicated the original work found no effects whatsoever.
the second one is known but is reported as a sexual potency improver?? no hint at all of psychedelic activity.

perhaps the benz {cd}indoles are the compounds for someone to make and taste to finally squash the dumb phenethylamine tryptamine LSD overlay theory.

 

[fastandbulbous]

^ Well considering all of the active psychedelics with a chiral centre that corresponds to the carbon at the 5 position all have the absolute configuration identical to that of LSD, it doesn't seem that dumb to me.

The N,N-dipropyl 2-aminotetralins (compound 2 minus the pyrrole ring) are dopamine agonists, but they don't have the indolic nitrogen for binding - doesn't mean compound 2 will have a similar pharmacological profile (the addition of the indolic pyrrole ring is a big change in the molecule)

 

[wirreddreams]

Both those compounds look interesting

 

[nuke]

compound 2 the benzcdindole:
they are it seems fairly selective 5-HT 1 (whatever) agonists and also D2 agonists which inhibit prolactin release.
there is no proper data that I can find on the unsubstituted coupound 2, most of those looked at were N-n-propyl or N methyl.

neither of these two are active psychedelics afaik , the first is an artifact and people wh replicated the original work found no effects whatsoever.
the second one is known but is reported as a sexual potency improver?? no hint at all of psychedelic activity.

Interesting to having been reported as a sexual activity improver.. I guess if you can inhibit prolactin release to some extent you can stop the refractory period after an orgasm, and if you have D3 agonism, you can get increased impulsivity/sexuality a la Mirapex.

 

[Black]

i've thought of compound 2 myself when looking to combine elements of lsd and dmt in one molecule. i would be very interested on any information on it. though my bet would be that the N,N-dimethylamine is active while the unsubstituted amine is not.

perhaps trying these compounds could shed some light why N-methylating phenethylamines attenuated psychedelic activity while N,N-alkyl substitution is necessary for tryptamines, as the structure is right between tryptamine and phenethylamine…