• N&PD Moderators: Skorpio | thegreenhand

I Like to Draw Pictures of Random Molecules

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Wittig reaction can do that, with the phosphonium salt made from MOM-Cl and a trialkylphosphine (I don't know if PPh3 is the best, and they don't work so well on ketones sometimes, so maybe there are better conditions) and is undergrad level.

Wouldn't that be a nonstandard use of the Wittig reaction? The wikipedia entry shows the carbonyl being replaced with a C=C double bond, which looks vaguely familiar from o-chem all those years ago. Looks too complex for undergrad.
 
I'll give you a clue, that's hopefully vague enough - it's two undergrad level reactions, the first is a normal Wittig.

(I don't see this as being against the rules, but if it is, I apologise and feel free to delete it)
 
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How would someone go about drawing different kinds of bridged tropane analogs, like this:

BridgedPhenyltropanes.jpg


But with the tropane as a cycloheptane ring?
 
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Tropanes are bridged cycloheptane rings. I'm not sure what you mean?
 
Tropanes are bridged cycloheptane rings. I'm not sure what you mean?

Bridged as in the previous examples, a ring as in a literal visual ring depiction, e.g.:

ChemDraw puts out cocaine like figure A:

bridgeclarify.jpg


I want to draw figure C like figure A, not like figure B. So I can modify it in ChemDraw.
 
So the shaded orbital lobe is unnecessary, the wedge bond comes out from the ring and not to the nitrogen? Thanks
 
The shaded bit represents the nitrogen lone pair, weather you draw it or not depends on what you're trying to show. You can also just draw it as a pair of dots next to the nitrogen (representing the two electrons) like this N: which is easier I think.

I'm not sure what you mean about the wedged bonds, there are several ways you could show the stereochemistry, I just picked the way I thought was best.
 
An amateur psychedelic chemist's wet dream

th_DMDMA.jpg


Dimethylenedioxy-dimethamphetamine.

Looks alien, doesn't it?

I suspect that the double-para configuration has no activity whatsoever. This probably doesn't either.

Edit: Another one:

LisMDMA.jpg


Lismethylenedioxyamphetamine (LisMDA)

Whenever MDA is approved for long term medical use, it'll probably be in this form. (took the idea from Vyvanse)
 
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Prodrugs from stims. That reminded me of phenmetrazine & phendimetrazine....

BTW, could anyone find me a picture of cocaine with all the positions numbered like in this image of morphine?

es5Bas2.gif
 
Ah, I didn't realize he was talking about adding a carbon-carbon bond, guess I misread it.

I'll give you a clue, that's hopefully vague enough - it's two undergrad level reactions, the first is a normal Wittig.

(I don't see this as being against the rules, but if it is, I apologise and feel free to delete it)

Hmmm, I can definitely see it in three reactions -- but not two, at least off the top of my head. I'll shoot you a PM though so we don't get in trouble. :)
 
So far Methoxetamine has been a miracle drug in my opinion, don't ask....though i was wondering if anything could be done to give it come 5-ht activity, and possible decrease duration a little bit.

Would you all think it's methoxy group responsible for the duration, or rather the position on the ring?

The great resemblances with tramadol makes me wasnt to investigate this compound a bit further.
 
One day we'll evolve and everyone will see the fundamental love, and have MDNA in their nuclei. ;)

30sbn7b.png
 
I'll give you a clue, that's hopefully vague enough - it's two undergrad level reactions, the first is a normal Wittig.

(I don't see this as being against the rules, but if it is, I apologise and feel free to delete it)

The original post asked, "What is it called when you change a ketone to an aldehyde?" That sounded to me like there should be a single named reaction that does this. It would be fun to take up your challenge to figure out a way to do it in 2 or 3 reactions, but I never used my o-chem knowledge after college, so it would require a bit too much re-learning and mental effort for me at this point.
 
Navarone, it is pretty close to tramadol isn't it. I've no idea how you could make a kinda hybrid of the two though. Wouldn't shortening the N-Et to an N-Me as in ketamine reduce the half-life? Or is it the chloro in ketamine that somehow makes the duration so short, seems unlikely I think?

Haha Solipsis, but I think you might need a few more hydrogen bonds for stability, check out the G-C base pair:

GC_base_pair_jypx3.png
 
N-ethyl to N-methyl does reduce potency/duration for arylcyclohexylamines, IIRC.
 
From what I've read on Wikipedia, lengthening the N-methyl to a N-ethyl simply increases potency, this was demonstrated on a study about arylcyclohexylamines (eg: PCP) analogues with ethylcyclidine being the most potent out of the classic arylcycloamine.
See:
http://en.wikipedia.org/wiki/Phencyclidine#Structural_analogues
And
http://upload.wikimedia.org/wikipedia/commons/7/78/ACHA_SAR.png
[Note: it pisses me off i cant post .png pictures on bluelight ARGHH]

Tiletamine was one of the newest analogues which seemed to exert more potency and duration than PCE, in fact it also ha a N-ethyl but I guess the rate at which the alkyl is cleaved is just as fast as for N-methyls, it is very likely that the boost in duration and probably also potency was due to the thiophene additin.

In the case of methoxetamine, Rick james would say: "Methoxetamine is one fucking hell of a drug!"

(Ow man I'm craving for some MXE so bad right now...250mg MXE + 3g piracetam + 1mg clonazepam IV was the most mindblowing experience of my life, a mindtrip far above LSD)
 
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