I Like to Draw Pictures of Random Molecules

[flying-potato]

4-metoxymethyl-methcathinone :

 

[roi]

Fluoroadamantate. Or something.

 

[clubcard]

The two molecules I drew are mostly planar.

But they aren't in real life unless you make them rigid and even then, the lowest energy-state might not be planer.

 

[aced126]

But they aren't in real life unless you make them rigid and even then, the lowest energy-state might not be planer.

Where can they rotate? Guessing there will be 4 isomers for each of the molecules, one of which will probably be of the right conformation. The non substituted one (ritalindane maybe?) will probably just act like ritalin. Not so sure how effect of an SRA will the other molecule be. Will probably just inhibit reuptake of 5HT.

 

[clubcard]

an MD itself isn't totally planer - look into the bonding-angles as described by VSEPR theory. The lowest energy state is when the bonds are closer than their natural angles. Look at ammonia - the lone-pair means that the shape is a 3-sided pyramid. That's why you need software to see it in 3D. Speed isn't flat and ritalin (or it's reversed ester) are miles from being planer.

 

[clubcard]

Fluoroadamantate is an interesting idea. What about just having that methyl on the thiophene homologue of MPA? If that shows serotonin-releasing activity, an MD has a good chance of working. You would need the methylamine and optical resolution BUT you could do it.

 

[roi]

Fluoroadamantate is an interesting idea.

Inspired by bromantane, obviously. Any idea if there's more research into adamantane stimulants? Also your inbox is full, go delete old messages

Methamadatamine

Bonus:

 

[clubcard]

Requires an aromatic (flat & binding in lipophilic pocket via Van der Waals forces.

 

[Nagelfar]

Requires an aromatic (flat & binding in lipophilic pocket via Van der Waals forces.

Would an endo-etheno bridge on a cyclohexane fit to that specification or is it not flat by its internal linkage (as rendering tools usually default it to a boat conformation if its not held in a specific way to other constitutents)?

Same molecule weight I'm assuming.

Since the double bonds rotate in benzene, is there another conformation where the same would be the case, holding a stable rotating type structure within a 2D-planar fixed molecule?

 

[adder]

Would an endo-etheno bridge on a cyclohexane fit to that specification or is it not flat by its internal linkage (as rendering tools usually default it to a boat conformation if its not held in a specific way to other constitutents)?

It would make the structure even "more three-dimensional", besides no conformation of cyclohexane is really flat with half of the hydrogen atoms being axial while in aromatics hydrogen atoms are perfectly aligned with the plane of the ring. Aromatic rings usually interact with aromatic rings of amino acid residues (in some cases they can also interact with carboxyl groups, which are also flat, proper substitution with an electron-withdrawing group on the ring is necessary, I guess, as plain alkylbenzene moiety is not electronically predisposed for such an interaction, e.g. cocaine's ester interacting with a tyrosine residue at DAT). It's certainly the case for stimulants related to amphetamine which when bound to DAT has its aromatic ring placed in a region with a few aromatic rings to interact with. Look up propylhexedrine which has mainly adrenergic effects. Wikipedia states it has psychostimulant properties at doses much higher than therapeutic ones, but somehow I doubt it could get any better than levo-methamphetamine at any dose.

Since the double bonds rotate in benzene, is there another conformation where the same would be the case, holding a stable rotating type structure within a 2D-planar fixed molecule?

What do you mean by that? The bonds constituting the ring can't rotate for sure, they're not really double bonds either, each carbon atom of the benzene ring has an unhybridized p orbital with one electron in it and these 6 p orbitals create a pi system in which all 6 bonds are equivalent in length.

BTW, a few weeks ago we discussed whether 1-(2,3-dihydro-1,3-benzoxazol-6-yl)propan-2-amine would be a stable compound, I've checked and it might be. Apparently benzoxazoline can be easily made in a similar manner as benzodioxole, no sophisticated methods needed. N-acylbenzoxazolines seem stable with respect to the position between N & O atoms, so plain benzoxazoline should be stable enough to survive subsequent steps in the synthesis towards the target compound.

 

[Nagelfar]

It would make the structure even "more three-dimensional", besides no conformation of cyclohexane is really flat with half of the hydrogen atoms being axial while in aromatics hydrogen atoms are perfectly aligned with the plane of the ring. Aromatic rings usually interact with aromatic rings of amino acid residues (in some cases they can also interact with carboxyl groups, which are also flat, proper substitution with an electron-withdrawing group on the ring is necessary, I guess, as plain alkylbenzene moiety is not electronically predisposed for such an interaction, e.g. cocaine's ester interacting with a tyrosine residue at DAT). It's certainly the case for stimulants related to amphetamine which when bound to DAT has its aromatic ring placed in a region with a few aromatic rings to interact with. Look up propylhexedrine which has mainly adrenergic effects. Wikipedia states it has psychostimulant properties at doses much higher than therapeutic ones, but somehow I doubt it could get any better than levo-methamphetamine at any dose.

Very insightful, I thank you for the time taken in this back and forth to be so clear and thorough with your response.

So as for my original curiousity: are there any other structures like benzene that are flat but even out on the atomic level to be a pure shape such as "pi" (another shape but unusual in the same manner, a idiosyncratic "default" orbit?) anywhere in the literature? Getting into mathematical "real numbers" and such e.g. a pure sphere instead of a (pi) circle? A molecular tesseract? One taking on the golden ratio to exacting dimensions or Pythagoras' theorem or a torus, a Möbius strip molecule? Any examples of eletron quantum entanglement of two places on the same molecule making interesting properties? I suppose it's a loaded and long winded inquiry I made of that. ;p I mean, for a simple answer, anything that *functionally* substitutes for a benzene in most all circumstances, would be what I'm looking for moreso than the novelty seeking I've dished out above.

What do you mean by that? The bonds constituting the ring can't rotate for sure, they're not really double bonds either, each carbon atom of the benzene ring has an unhybridized p orbital with one electron in it and these 6 p orbitals create a pi system in which all 6 bonds are equivalent in length.

I don't mean rotate like "freely-rotatable" (I mean, phenyls rotate the benzene on their methyl branch in 3D if I'm not mistaken). Perhaps I misunderstood how that they "are not really" double bonds (which I knew, but misconstrued?) in my reading up on that some time ago; thus why sometimes benzenes are drawn as a cyclohexane with a plain circle in the middle (to denote that they aren't truly double bonds but such is a convenient way of rendering them). I thought where the double-bonds were didn't matter because they were continually flowing from one bond to the next like a wheel; but if they're just equally bound in "a perfect Pi circle" as a static & stationary structure, that makes sense. But philosophically speaking, the particle/wave dimorphism posits that they are all undulating in perpetual minute permutations continually. (I suppose I am being, yet again, pedantic.)

BTW, a few weeks ago we discussed whether 1-(2,3-dihydro-1,3-benzoxazol-6-yl)propan-2-amine would be a stable compound, I've checked and it might be. Apparently benzoxazoline can be easily made in a similar manner as benzodioxole, no sophisticated methods needed. N-acylbenzoxazolines seem stable with respect to the position between N & O atoms, so plain benzoxazoline should be stable enough to survive subsequent steps in the synthesis towards the target compound.

I'm willing to stake my post count that you're getting a conversation we've had mistaken with anothers on this particular subject; phenethylamines are a class so over expounded upon within the demographic of interests on this particular forum, that I don't even think I've ever discussed any potential or attested one here in depth. (I'm more of a DRI & opioid guy than empathogen & DRA aficionado)

BUT, anybody care to draw a random molecule inspired by this beaut? -> 3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one (super-simple 1-step synth opioid)

 

[pharmakos]

aren't all the bonds in benzene technically 1.5pi bonds?

 

[clubcard]

Thanks for putting that up, N. I had to do U47700 and it was sheer hell. They KNEW it was important but were concerned that only PRIMARY sources were referenced. I mean - THAT IS ALL THAT'S OUT THERE!
I would strongly recommend that you also add Lednicer's parent compounds for BDPC. 4-(dimethylamino)-4-(4-methylphenyl)cyclohexan-1-one & 4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one were both equipotent. I asked him why he hadn't tried MDPC... and he said that he simply forgot! WHY a bromine & methyl worked equally well for the simple cyclohexanones is a mystery - but an interesting one.

I really think you should obtain a copy of Chemoffice by hook or by crook. I want us all to be able to just use SMILES to transfer compounds and the IUPAC name is generated. I don't know how much the student edition costs but it's like Word for the PC. Yes, there alternatives but even in The Ukraine, they use it, allowing me to describe compounds to them. I know it isn't cheap, but when you have it, you will wonder how the hell you managed before.

It calculates minimum-energy conformations and allows 3D overlays. The patent I posted concerning the 'reversed ester' of nortilidine has to be seen... especially when the active isomer of cypenamine overlays perfectly. I've heard Dutch, Belgian & German people say that they take tilidine before an exam because it lets you focus. No surprise when you realize it's increasing the amount of dopamine into the body via 2 different actions. OK, it's too much work but it's fun to work out a chiral synthesis. I spent a full day on it and I was pretty proud of myself... well, not pride, more like seeing what nobody else has seen, EVER within the synthesis.

Medicinal chemistry is an art AND a science. People like Adder are good examples of brains and creativity.

BTW it appears in one years 'Journal of Medicinal Chemistry', I will dig it out for you. But you have to admit, 1-step name-reaction.

 

[Dresden]

Thought I'd draw out those structures you mentioned if you don't mind. It makes me happy.

4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one

4-(dimethylamino)-4-(4-methylphenyl)cyclohexan-1-one.

This next molecule was designed so that I could draw out another cool looking new molecule; from a pharmacologically predictive standpoint here, however, it is more likely to elicit groans. Just remember why I drew it (Because I like to draw pictures of random molecules!!!):

This is my favorite thread EVER! Thanks roi for introducing me to http://opsin.ch.cam.ac.uk!

 

[Nagelfar]

Thanks for putting that up, N. I had to do U47700 and it was sheer hell. They KNEW it was important but were concerned that only PRIMARY sources were referenced. I mean - THAT IS ALL THAT'S OUT THERE!
I would strongly recommend that you also add Lednicer's parent compounds for BDPC. 4-(dimethylamino)-4-(4-methylphenyl)cyclohexan-1-one & 4-(4-bromophenyl)-4-(dimethylamino)cyclohexan-1-one were both equipotent. I asked him why he hadn't tried MDPC... and he said that he simply forgot! WHY a bromine & methyl worked equally well for the simple cyclohexanones is a mystery - but an interesting one.

Put it on the BDPC page:

https://en.wikipedia.org/wiki/BDPC#Structure-activity_relationships

I really think you should obtain a copy of Chemoffice by hook or by crook. I want us all to be able to just use SMILES to transfer compounds and the IUPAC name is generated. I don't know how much the student edition costs but it's like Word for the PC. Yes, there alternatives but even in The Ukraine, they use it, allowing me to describe compounds to them. I know it isn't cheap, but when you have it, you will wonder how the hell you managed before.

My issue is that I don't have either a phone, computer, or internet connection WiFi or otherwise, I come to the library to use the computer on an almost daily basis. Five years as a street junkie took it's toll, now I got into a program where the gov't pays my rent, otherwise I'd probably be still under a bridge chasing the chemicals I am talking about. ;p

 

[Nagelfar]

Strobamine + " 7-(((1R,3r,5S)-9-Azabicyclo[3.3.1]nonan-3-yl)oxy)-2H-chromen-2-one " + C2-acetyloxy-cocaine

Some pretty good affinities, wonder if they gimp one another when put together?

Reminds me of some alternate drawings of some morphinans, e.g. 3-ethoxy-7,8-dihydro-morphinan-6-one as below:

EDIT:

So I started with the above two, hit the automatic clean up key, and got this hot mess:

As garbled lookin' as a neurotoxin

EDIT#2, also:

G-130 + 6-methyl-phenmetrazine + etc. = "2,2,3,3,5,5-hexamethyl-6-phenylmorpholine" add a crazy isomerism and get:

...as you can see I've been bored today and spending far too much time @ the library

 

[SONN]

anyone ever heard of an n-feruloylserotonin?

I wonder if you could stick a number of other tryptamines where the serotonin is? the study on n-feruloylserotonin said it had selective effects on stress in rodents, who knows what it does to humans but its in a number of preworkout supplements, including mine probably (considering theres carthamoides extract in mine)

I'd love to know if anyone finds any intriguing info on n-feruloylserotonin or related compounds

 

[Dresden]

RC fodder.

2C-SHIVA, a known stimulant but not, reportedly, a psychotomimetic.

 

[SKL]

RC fodder.

Does it have a name? Can we call it mescalone?

2C-SHIVA, a known stimulant but not, reportedly, a psychotomimetic.

That looks kinda interesting.

 

[Nagelfar]

anyone ever heard of an n-feruloylserotonin?

I wonder if you could stick a number of other tryptamines where the serotonin is? the study on n-feruloylserotonin said it had selective effects on stress in rodents, who knows what it does to humans but its in a number of preworkout supplements, including mine probably (considering theres carthamoides extract in mine)

I'd love to know if anyone finds any intriguing info on n-feruloylserotonin or related compounds

According to a quick search, it's found in safflower seed? I added a very meager stub of it to WP