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I Like to Draw Pictures of Random Molecules

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Spiroxetamine..
imgsrv.fcgi


12x more potent than ketamine (IC50 0.065uM v 0.86uM.. https://pubchem.ncbi.nlm.nih.gov/assay/bioactivity.html?cid=44370217 Add a methoxy somewhere?or a Halo? look pretty easy straightforward synthesis https://pubchem.ncbi.nlm.nih.gov/compound/44370217#section=Top
 
probably has a pcp type pharmacology, high logP etc... so long trips & high potency
 
It's the oxalate?
Inhibition of TCP binding to NMDA is not conclusive is it? I agree it is probably active and potency but binding is not the only factor, there's also Mg trapping?

What about first starting with that replacement of the carbonyl with aromatic function in K?:

2-(Chlorophenyl)-2-(methylamino)tetralin.png


2-(Chlorophenyl)-2-(methylamino)tetralin
 
^^ definitely closer to pcp than anything in terms of both pharmacology and pharmacokinetic may be with more stim effects than dissociatives..

^ yes the oxalate salt was used, but no special reasons for that really: It just crystallized easily from alcohol giving nicer crystalline solid than the hydrochloride. else there's no difference w/the hcl afaik

The 2-amino-2-aryl tetraline? it is probably quite potent but much like pcp though than K. the keto at the alfa of K, MXE..etc makes the pKa of the amine lower (ie less basic) which changes its distribution and/or binding mode at nmdar. But its looks neat ..
now wait a minute: I think the 2-amino-2-aryltetraline may also bind to opioids not sure how potently: at least one of the steroisomers! superimpose the structure with that of morphine or ethorphine: it overlays not too bad..
How about 2-amino-2-aryl-1-tetralone? I mean still retain the keto of K..MXE..?
 
^ Nice! I like the last one but 3 chiral centers + cis/trans = lots of stereoisomers?)
 
DotChem said:
^ Nice! I like the last one but 3 chiral centers + cis/trans = lots of stereoisomers?)
Click to expand...
sorry, not really advanced but.. i don't immediately see the cis/trans isomerism - is it on the "piperidine" subunit where the two chiral centers are next to each other? i guess i can see it now, i was just conditioned to only see it on C=C bonds %)
 
c60599ec25.png


there, is that better ? :) squiggly lines denote chiral centers and the two on the right form a cis/trans pair
 
But don't 2 of the substitutions have to be the same for them to be zusammen or entgegen each other? In this example above, there is no symmetry in the piperidine ring and rest of the molecule as seen from the bond you say has cis/trans or E/Z. If it would have just been a cyclohexane and nothing else on the left then you'd be right.

I'd say since there is no symmetry or interchangability you have (R,S), (S,R), (R,R) and (S,S) when talking about those chiral centers on the right. I've never heard of (R,R) and (S,S) being pairs, is that a thing?
edit: oh never mind, it is a thing then, when speaking of highest priority groups being together or not.

Doesn't add extra isomers to list though right? On top of just the permutations of the 3 chiral centers?
 
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There will be RRR RRS RSR RSS SRR SRS SSR and SSS so yes there are so many stereocenters,

Also note the the N- on the rightmost side which seems to be asymmetric too (sp3) but that is no chiral center bcos N can go "umbrella-like-flip" inversion easily with low energy barrier, som3 stereocenters are right (2^3=8 isomer)
 
Solipsis said:
But don't 2 of the substitutions have to be the same for them to be zusammen or entgegen each other? In this example above, there is no symmetry in the piperidine ring and rest of the molecule as seen from the bond you say has cis/trans or E/Z. If it would have just been a cyclohexane and nothing else on the left then you'd be right.
Click to expand...

I don't think it's a prerequisite for cis/trans notation, you can basically use it with respect to any two substituents on any cycloalkyl ring, so specifying to which substituents the notation refers is preferable if necessary to exclude ambiguity. If you take bromadol for instance, I suppose you could pair any two substituents at C1 and C4, and name their relationship as cis or trans, but the tendency may be to choose functional groups rather than alkyl substituents from what I've seen. It is pretty loose and not official nomenclature. As for E/Z notation, if there are more than 2 substituents along a double bond the Cahn-Ingold-Prelog system is used to establish the two substituents that determine the stereochemistry, no ambiguity is ever present with this notation.
 
sekio said:
c60599ec25.png


there, is that better ? :) squiggly lines denote chiral centers and the two on the right form a cis/trans pair
Click to expand...

Lol, I'm actually a little bit confused by this drawing. I assume the squiggly lines denote that the carbon atom og group can go either into the "paper" or towards the viewer. What confuses me is that I thought that single carbon-carbon bonds could swivel around freely in all directions. Have I misunderstood that? Is it because they can only swivel around their own axis?

But the consequence of that, is that it would be possible to have cis/trans isomerism without a double bond? wtf, what am I missing? :D
 
the swirly lines denote chiral centres... basically, where there is a chiral centre, the molecule isn't the same if the substituent faces in the one or the other direction.

imagine methane with four different substituents: there are two ways to arrange the molecule (two mirror images), and you cannot get one of those to become the other by turning it around in any way. it's asymmetric, and hence two stereoisomers (enatiomers) exist.
 
You forget to imagine hydrogen, C has 4 bounds and H atoms isnt present in drawing, so you cant "swivel" it to make the stereoisomer
 
when there are a pair of chiral centers next to each other, there is a cis/trans or erythro/threo/meso relationship :)

you are correct about the swirly lines meaning the bonds can either stick out front or behind the paper. however only sp3 carbon bonds that are unconstrained can rotate - like the bond between the two carbons in ethane. if it's constrained in a ring then bond rotation would invert or pucker the ring and there can be a singificant energy barrier to that.
 
I wanna learn this better!!

How do you do this?? Always wanted to know if you can make like a mdma-dxm-psilocybin(or psilocin)? Anything like that haha
 
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