I Like to Draw Pictures of Random Molecules

[Dresden]

^--That's cool.

Anyway,

I just thought of another indole. This one expanded my IUPAC nomenclatural vocabulary skills a bit, which you will understand when you see its name:

N,N-dimethyl-2-(6H-indolo[4,5]furan-8-yl)-ethanamine

Note the similarity between this tryptamine's indolo-4-(pseudo)vinyl substituent and LSD's indolo-4-"vinyl" position.

Finally for this post,

N,N-dimethyl-2-(5-methylthioindol-3-yl)-ethanamine aka 5-MeS-DMT

Obviously this one is just a simple O-->S (thia) analogue of 5-MeO-DMT, which is found in certain toads' venom.

Ok, just 3 more:

1-(1-aziridinyl)-2-(indol-3-yl)-ethane

Hellacious.

N,N-dimethyl-1-amino-2-(5-cyclopropylindol-3-yl)-ethane

Looks delicious to me. And...

N,N-dimethyl-1-amino-2-(5-(furan-2-yl)-indol-3-yl)-ethane

Funky!

I don't know what to say here, other than all of these should be synthesized and tested for activity.

 

[Nagelfar]

cocaine with a cis-propenyl (a la as the phenyltropane "RTI-11w" has, but not where it has it at the 4' position of the carbon ring; but at the other putative binding site…) …at the end of the extended carbmethoxy (Singh's 201c analog), the benzoyl changed considerably, linkage and ring both, a methyl tail on the tropane at an area that isn't on the bridge (the so-called 6/7 substitutions), etc.

 

[aced126]

 

[aced126]

 

[pharmakos]

i feel like that is most likely active. whether "activity" means horribly toxic or incredibly psychedelic, idk, but it looks like a simple enough modification that it should do something.

 

[Pomzazed]

^ Aziridines are too unstable and will spontaneously form covalent bond with N or O which comes into contact.
It's even more reactive than epoxide in most of the case.

 

[pharmakos]

so if it does make it to a receptor intact it could possibly irreversibly bind?

 

[yaesutom]

^--That's cool.

Anyway,

I just thought of another indole. This one expanded my IUPAC nomenclatural vocabulary skills a bit, which you will understand when you see its name:

N,N-dimethyl-2-(6H-indolo[4,5]furan-8-yl)-ethanamine

Note the similarity between this tryptamine's indolo-4-(pseudo)vinyl substituent and LSD's indolo-4-"vinyl" position.

I've heard speculation on these boards that 4-vinyl-DMT might be active and good/potent, and then there's the speculation about 4-HO-5-MeO-DMT so this is sort of a constrained version of that. Looks tasty to me. I really hope the research chem companies explore 4-XYZ-DMT's.

 

[aced126]

Rigid analogues of DET. Using Nichols' rigidifying technique to see what part the alkyl groups play in the bonding of the molecule to the receptor. However in this case bond rotation is possible which is not the case with amides.

 

[Dresden]

Oops, my bad then. Scratch the aziridine thingy.

As for the more XYZ-tyrptamines comment, I agree. In TiKHAL, Sasha Shulgin largely ignored the various possible indole substitutions to focus on the N,N-ones instead apparently.

 

[roi]

Few stimulant ideas:

Bonus:

 

[Nagelfar]

Dextrorphan + Salvinorin A, from my idea of a drug, the rationale of which is mentioned at this post/thread, that has the subjective affect of Salvia Divinorum and is also a dissociative anaesthetic NMDAR antagonist, with the purpose of having the contrast of both altered states at once with one drug.

(P.S. I did the 'automatic "clean-up"' feature, and this is as straight as the cock-eyed chemical can be rendered, apparently)

 

[pharmakos]

wow. looks like a masters project if you ever wanted to synth it. very interesting.

 

[sekio]

triazole-methylphenidate? wonder if it would be an antifungal too.

so if it does make it to a receptor intact it could possibly irreversibly bind?

possibly, but in this case i would expect it to tautomerize to N-vinyl tryptamine & probably decompose from there.

with the purpose of having the contrast of both altered states at once with one drug.

now if i was a betting man, i'd say this is more likely to be neither...

 

[roi]

..It's way to damn easy to invent new stimulants. So many options.

 

[Soulfake]

 

[neurotic]

I liked the nico DMT. Psilocin prodrug?

 

[Dresden]

Yes, in all likelihood.

Speaking of "nico" (sort of), I've often thought about this one:

2-methylamino-1-(pyridin-3-yl)-propane

and

2-methylamino-1-(pyridin-4-yl)-propane

But, in today's methcathinone crazed RC market, these two are more likely to hit the mailboxes:

2-methylamino-1-(pyridin-3-yl)-propan-1-one

and

2-methylamino-1-(pyridin-4-yl)-propan-1-one

The third one has already been mentioned by someone in this thread IIRC.

 

[Soulfake]

I liked the nico DMT. Psilocin prodrug?

yes that´s what I had in mind.

 

[Dresden]

I like your N,N-dimethyl-4,4'-di-tryptamino-ether idea for its symmetry and relative metabolic stability if nothing else. I was wondering, however: Did you mean for the beta carbon to the N of your piperidine ring in your next to last structure above have a methyl group, or did you mean for the N-alpha carbon to have one instead?