I Like to Draw Pictures of Random Molecules

[Solipsis]

Yeah it's an intermediate.. but I can check Shulgin's last big book to see if I see any PEA's with an extra methylene spacer.. (let alone an aldoxime, which just seems reactive))?

 

[roi]

There's some stuff like (+)-CPCA with that spacer, but it's heavily modified. The N-hydroxy group shouldn't matter much, but that doublebond? No idea.

 

[Nagelfar]

There's some stuff like (+)-CPCA with that spacer, but it's heavily modified. The N-hydroxy group shouldn't matter much, but that doublebond? No idea.

CPCA/nocaine is a DRI not a DRA; the carbmethoxy is just like that on cocaine & methylphenidate.

 

[malmet]

Question about planar rings and such; couldn't cyclohexadiene work as an isostere? It's a lot flatter than cyclohexane:

Amphetamine: https://i.imgur.com/wiFudTm.png
1,4-Cyclohexadiene analog: https://i.imgur.com/ipiNJDU.png
Cyclohexane analog: https://i.imgur.com/4TlqmpW.png

You have the hydrogens on the saturated carbons sticking out of plane but the rest is flat. It's not aromatic of course but I'm curious as to how it would work out.

 

[Nagelfar]

Question about planar rings and such; couldn't cyclohexadiene work as an isostere? It's a lot flatter than cyclohexane:

Amphetamine: https://i.imgur.com/wiFudTm.png
1,4-Cyclohexadiene analog: https://i.imgur.com/ipiNJDU.png
Cyclohexane analog: https://i.imgur.com/4TlqmpW.png

You have the hydrogens on the saturated carbons sticking out of plane but the rest is flat.

EDIT: Nevermind, I was thinking benzene, yes cyclohexadiene is closer to benzene than cyclohexane. Some of those cyclopentane isostere have a few hydrogens out of plane too, so I'd venture it a possibility depending on where and how it needs to fit.

 

[belligerent drunk]

Yeah it's an intermediate.. but I can check Shulgin's last big book to see if I see any PEA's with an extra methylene spacer.. (let alone an aldoxime, which just seems reactive))?

It would most likely hydrolyze into the respective aldehyde and hydroxylamine. The aldehyde would probably not be very useful.

 

[adder]

Probably a totally made up thing or an error, hydroxylamine is toxic.

 

[DotChem]

Question about planar rings and such; couldn't cyclohexadiene work as an isostere? It's a lot flatter than cyclohexane:

Amphetamine: https://i.imgur.com/wiFudTm.png
1,4-Cyclohexadiene analog: https://i.imgur.com/ipiNJDU.png
Cyclohexane analog: https://i.imgur.com/4TlqmpW.png

You have the hydrogens on the saturated carbons sticking out of plane but the rest is flat. It's not aromatic of course but I'm curious as to how it would work out.

cyclohexadiene is unstable under normal conditions: easily oxidized by air to give the corresponding benzene (driving force = aromaticity energy gain). This is the reason why products of such compounds always contain [Oxidation] inhibitor such as BHT. But if one of the two sp3 carbons of the cyclohexadiene is di-substituted (say by 2 methyls), then it should be fine. But disubstitution of one of these carbons will make you loose even more in terms of planarity of the system).

 

[DotChem]

MXE: open wide

 

[adder]

If you want to replace the cyclohexyl in ketamine with a phenyl ring, then it can't have the keto moiety.

You can't have both the amine and the aryl group either, you end up with biphenyl or a substituted aniline.

 

[Jaw Clenching]

Thanks for the input @solipsis

It seems that I am on a kick with -FLY derivatives. They interest me a lot. I was wondering if any of the following -FLY derivative would be in theory psychoactive at all.

Thanks!

Did you see these ones I came up with?

http://www.bluelight.org/vb/threads...-molecules?p=13637715&viewfull=1#post13637715

http://www.bluelight.org/vb/threads...-molecules?p=13637708&viewfull=1#post13637708

http://www.bluelight.org/vb/threads...-molecules?p=13637699&viewfull=1#post13637699

Not sure if some of those are even possible to make.

I couldn't find any molecules that have a Pyrrole group attached to an Indole group - basically di-indole or something.

Here's an example to better visualize what I'm saying:

 

[Nagelfar]

Question about planar rings and such; couldn't cyclohexadiene work as an isostere? It's a lot flatter than cyclohexane:

Spoiler: Large images

Amphetamine:

1,4-Cyclohexadiene analog:

Cyclohexane analog:

You have the hydrogens on the saturated carbons sticking out of plane but the rest is flat. It's not aromatic of course but I'm curious as to how it would work out.

cyclohexadiene is unstable under normal conditions: easily oxidized by air to give the corresponding benzene (driving force = aromaticity energy gain). This is the reason why products of such compounds always contain [Oxidation] inhibitor such as BHT. But if one of the two sp3 carbons of the cyclohexadiene is di-substituted (say by 2 methyls), then it should be fine. But disubstitution of one of these carbons will make you loose even more in terms of planarity of the system).

Spoiler: Nothing to do with the idea, just in there and big

Check out the two position, though the cyclohexadiene idea is on the three position where the arene is.

it looked like this:

...and, ironically, made the H saturated angles connected with the hope that it would come out more planar with a single carbon linking two more internal/inward-facing methylenes:

(not thinking, that duh, the one carbon between two linkers is CH₂ still; could just double-bond those two but the 2D result isn't as aesthetically pleasing for a random molecule to show off)

and upon "cleaning" it got the rectangular box of the first image. Is that thing even physically possible? Tenable?

And finally:

Some kinda naphthdiene-endo-ethendio

...if you 'clean up' the image automatically in Marvin Beans.... it transforms into

...Gengar the Pokémon:

 

[belligerent drunk]

You can't have both the amine and the aryl group either, you end up with biphenyl or a substituted aniline.

Yeah I didn't consider that the carbon is already quaternary. My bad.

 

[Bagseed]

at least this one won't be possible in my opinion. sp2 hybrid orbitals are oriented in a planar fashion. so you cannot have these bonds from the C=C sticking downwards the way they do. energetically extremely unfavorable.

also this diazo group forming the 3-ring will be extremely reactive and might disintegrate very fast to release nitrogen gas (possibly leaving behind a carbene which is very reactive and might turn the olefine into an alkine).

 

[Nagelfar]

at least this one won't be possible in my opinion. sp2 hybrid orbitals are oriented in a planar fashion. so you cannot have these bonds from the C=C sticking downwards the way they do. energetically extremely unfavorable.

also this diazo group forming the 3-ring will be extremely reactive and might disintegrate very fast to release nitrogen gas (possibly leaving behind a carbene which is very reactive and might turn the olefine into an alkine).

Yeah well it was rather fatuitous, as my work if oft meant to be; but what of the one above it?

 

[Bagseed]

well, to be sure one would have to model the exact bond angles of that thing... sp3 carbon is most comfortable with a nice tetrahedral (~109° bond angles) structure, I guess there will be some strain on the bonds, but I have no idea if it will be practically possible.

 

[LaGaFàNi]

Totally new here, but I've got some 700 arylcyclohexylamine molecules schemed out on pdf / jpeg (according to the possible substitutions listed on wikipedia..) If any interest at all, I'll post them w/pleasure!

 

[Nagelfar]

Back to malmet's cyclohexadiene idea; would this be stable? -

 

[Nagelfar]

Fentanyl + O-desmethyl-tramadol (the methoxys)

 

[roi]