Possibility of new PCP and MXE analogs

[Montana Industries]

Hallo my friends,
I'm in love with Arylcyclohexylamines and on my search for new Synth routes, I found a way to synth Structurally new Derivatives of PCP and MXE.
MXE also called 3-Meo-2-Oxo-Pce is a very nice Substanz, but has the Problem of different activity because of the two possible stereo isomeres.
The possible derivativa 3-Meo-2,6-diOxo-Pce dont have this problem i think and has maybe new and good psychological activity.
For the PCP derivativa I cant find the correct Name, so I must going to define it.
It have the standard Pcp structure with an ether brige on the Cyclohexane-ring at the 2' 6' position, like the dione.
To the right time i test this compounds, but its nice to hear what do you think about it.

Have thanks and a fucking freaky weekend.
Mfg Mr.Montana

Self drawn pic of the structures:
http://www.bilder-upload.eu/show.php?file=94b73b-1438406441.jpg]

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[adder]

I'm not really sure what you've drawn because the picture is too small and I'm sorry but I can't see how you eliminate the existence of stereomers with these compounds. They are indeed pairs of two enantiomers. That ring constraint in the 2nd compound just won't work to substitute for the carbonyl group in MXE and I can't even picture an easy enough way to make it to make time spent synthesizing it worth it.

I think it would have been better suited for this thread.

 

[Montana Industries]

Adder thx for the reply,
Pcp doesn't have enatiomeres, so mxe have it because the extra carbonyl group.
The side of the carbonyl group, next to the phenyl group or next to the piperidine is what makes the difference.
So, when both sides , next to the phenyl and next to the piperidine ring have an carbonyl group may eliminate the stereocenter.
And the second was thought as pcp analoge, not for Mxe.
The Synth is easy to do with otc chems, but nothing like any of the public routes to arylcyclohexylamines.

Kind regards
Mr.Montana

 

[adder]

You do realise that ether bridge in the 2nd compound can be either on the side of the piperidine ring or the aromatic ring, don't you? Hence a pair of enantiomers as no more isomers are possible due to impossible constraints even though there are 3 stereocenters.

 

[Montana Industries]

Yes all right for the second compound, i know this and i've don't challange this fact.
I've said that at the 2,6-dione compound the stereocenter from MXE reserved and not about the etheral compound .
Thx

 

[Zeds(NCO2CH2CH3)2]

You sound like a foreign fisherman, trying to procure this through a Michael addition. The dione will probably exist as a distorted screwed up chair form, or not at all. Also it will be metabolically unstable.
Not going to work and the second example is just.. Wtf the ether bridge is in a couple natural products but good luck..

 

[Hammilton]

How about replacing that ether bridge with an alkyl bridge, like norbornane or tropane?

 

[Montana Industries]

Thanks for these informations Zeds,
what for natural occuring compounds do you mean?
I cant find much infos on interesting Oxetane containing Alkaloids.

You know about the activity of b-keto Amphetamines, and also about the b-Phenyl-(especially)Meth Amphetamine?
Both groups have aromatic properties and the replacement of the carbonyl group of Mxe/Ketamine with a Phenyl group might have some nice activity too.
And 2-phenylcyclohexanone is easy going to synthesis.

Hi Hammilton,
Its sounds good but comparing with Tropane sounds bad to me, because 1-Benzylcyclohexylpiperidine has anticholinergic effects on Pcp's potency.
So its a easy possibility that this effect the same and I love this Substances, because of ther nmda receptor activity.
And the way to synthesis is another thing thats maybe not easy.

Have Thanks and kind regards
Montana

 

[ungelesene_bettlek]

Montana Industries' drawing made bigger


The picture on the left of Montana Industries' drawing, redrawn using MarvinSketch. Looks like a reasonable MXE analogue to me - I'd give it a try.


The picture on the left of Montana Industries' sketch. A direct PCP analogue, it seems like, but..


this is the same molecule after MarvinSketch running its optimisation algorithm over it. Obviously, through the modification in structure, the hexane ring got into its "boat configuration", whereas, as far as I know, it is usually in its "chair configuration in arylcyclohexylamines (correct me, if I'm wrong, please). That's why I somehow doubt it would be active...

https://en.wikipedia.org/wiki/Cyclohexane_conformation

 

[Zeds(NCO2CH2CH3)2]

Spot on above poster these are poor suggestions by what appears to be another foreign fisherman looking for easy ways to synthesize these compounds. Montana it was a good effort..

Hamilton, as you know your colleague has synthesized varied bridged alkyl cyclohexanes with varied activity so I am unsure of the question I believe I might even misinterpreted it..

Zedz

 

[ungelesene_bettlek]

Spot on above poster these are poor suggestions by what appears to be another foreign fisherman

Yes, I am a "foreign fisherman", as I have already confessed in in this posting.

But I am not "looking for easy ways to synthesize these compounds", because, although being a natural scientist, I am a whole-hearted theoretician and not an experimentalist. And, amongst other things, I think I can say I'm pretty good with computers. And that is why I started MarvinSketch after reading the first two posts here, because adder complained that he could not properly see what Montana Industries had drawn. I even confess that I haven't read the rest of the thread in full length yet, but I will within the next few days when I get the time.

To make a long story short: yes, I am basically a layman in psychopharmacology, but I am not a moron. All I wanted to do is just helping out with nicer pictures. If that is a crime, I plead guilty, so come on and sue me.

 

[Zeds(NCO2CH2CH3)2]

Oh you misinterpreted, Montana is fishing for synthetic advice. You are fine, was a solid statement on the chair conformation activity. Good work

Zedz

 

[clubcard]

If you want something close to K, you don't NEED the PCA scaffold. Try overlaying DXM and MK-801. Or, if you want a cert - isophenidine felt identical to K to me....

 

[blueberries]

Dammit! That's my PC-ABC! Or similar to it.

Can I claim intellectual property here? It's like my child! I thought of it a few months back and have been pitching it to several chemists. I figure it'd be like PCPy but less potent and more NMDA antagonsty. Also the name is just golden.

 

[clubcard]

Something very similar has been patented. That had the piperidine ring with an extra cyclohexane ring from joining the 2 & 5 positions of the piperidine ring.

 

[Montana Industries]

Ungelesene_Bettlektüre have big thanks for doing this, i'm bad in such things

I don't want to fish any advice here, i will that people know about this substances.
I'm interrested what people think about it and the possible pharmacological activity.

And what are you thinking about 1,2-Diphenyl-Cyclohexyl-Piperidine?
It is Pcp and Diphenidine in one...^^

Kind regards

 

[ungelesene_bettlek]

Oh you misinterpreted, Montana is fishing for synthetic advice. You are fine, was a solid statement on the chair conformation activity. Good work

Oh, OK, sorry for misinterpreting. Hearing I'm doing "solid work" from someone as knowledgeable as you really means lots to me!

Ungelesene_Bettlektüre have big thanks for doing this, i'm bad in such things

You're welcome, dude, I really like to draw molecules using MarvingSketch! It didn't cost me much time and was really enjoying doing it!

 

[Dresden]

Not so sure about the stability of those, but don't let that stop you.

 

[dopamimetic]

The 3-MeO-2,6-diOxo-PCE certainly looks interesting. But how about the metabolic stability / possible toxicity of that diOxo moiety? I know far too less about metabolism, could be completely wrong, just reminds me of the liver toxicity of Pemoline...

 

[sekio]

If anything, it's closer to glutethimide or the barbiturates, not pemoline.