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The Big & Dandy 4-MeO-PCP Thread

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IlostaMadge

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Ripped straight from another forum, seems to be more at home here, nestling down amidst the psychonauts.

4-MEO-PCP looks to be of interest and appears to be legal. Any experience with it?
http://www.erowid.org/archive/rhodiu...4-meo-pcp.html

4-methoxy PCP has been previously tested in animals and found to be somewhat less potent than PCP itself. Results with human volunteer confirm this. A rough estimate would be 70% as potent. This is still significant, considering how potent PCP is.

A possible advantage of this analog is decreased duration of effect. This is because the 4-methoxy group provides a site for metabolism and elimination of the drug. This is a significant point, because the extended action of PCP is a real disadvantage in cases of acute overdosage.

For those that are unfamiliar with the effects of these compounds, the experience is very hard to describe. The most commonly known compound that is directly comparable is ketamine. Ketamine's effects are quite similar to PCP and 4-methoxy PCP, but K. is much less potent.
Would I be correct in predicting it's structure below: -





Would I be correct in assuming it's shorter duration would reduce the neurotoxicity?
Comments, critiscisms, thoughts or downright insults welcome...
 

Ham-milton

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yes, this is 1-(4-methoxy-1-phenylcyclohexyl)piperidine.

I know this because of ilabs.acdlabs.com's (I think that's right) free web-based iupac naming software. You just draw it in with a messier version of the applet sigma-aldrich uses in their substructure search, click on the main page and all of a sudden, you get your answer.

Really nice software, and useful for chem neophytes like me.
 

IlostaMadge

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Most definitely, see the ring containing the nitrogen, that binds to an incredibly specific receptor the Prg (propaganda receptor in full) this releases neuron inhibitions when firing motor controls, and causes a violent reaction to both police and stationary vehicles.

It's thought to work in the same way as the SKKW receptor (skunkweed) that causes a specific predisposition to violence and mental illness, only weed 14x stronger than the 70's weed smoked by politicians seems to bind though.

thats not right, but it sounds wonderful!
The structure I drew isn't right, or the IUPAC name Hamster came up with?

If it's the structure, could you please correct me?
 

Sturnam

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Ham-milton said:
yes, this is 1-(4-methoxy-1-phenylcyclohexyl)piperidine.

I know this because of ilabs.acdlabs.com's (I think that's right) free web-based iupac naming software. You just draw it in with a messier version of the applet sigma-aldrich uses in their substructure search, click on the main page and all of a sudden, you get your answer.

Really nice software, and useful for chem neophytes like me.
i think i have the same software, and really, it just makes me more confused as to the naming. just when i think i've got it, it spits out some name that is COMPLETELY different than what i was thinking...

wouldn't this still be illegal? er..in the US at least. I thought the analog law covers any basic additions or substitutions to existing scheduled chems. i mean, 5-meo-dmt is technically unscheduled, but given that it's one methoxy group away from DMT, i think it would be very easily prosecutable.

but, i'm interested to hear if the methoxy group reduces the neurotoxicity.

*edit* i found this article
www*erowid*org/archive/rhodium/chemistry/pcp/sar.html#sarcyclo (sorry about the stars; working towards my 20 posts!)
details some SAR on PCP analogs and specifically talks about substitutions to the cyclohexyl ring. it basically says the only good that can come out of it is increased dopamine affinity, but i read on wiki that dopamine is responsible for most of the psychotic features of PCP. it also says the 2 or 4 methyl substitutions of the cyclohexyl ring will increase potency, but says nothing about methoxy's.
 
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ralf2

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The methoxy group is on the benzene ring, not the cyclohexane ring. If you just read the synthesis info it's obvious, as they use 4-methoxyphenyl magnesiumbromide when making it.
 

Ham-milton

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Yes, it's the 4-carbon of the precursor- but not of the final product; the 4-carbon is on the cyclohexane in the final chem- so they are indeed talking about mods on the cyclohexane.

I'm not sure what you mean. The article is talking about mods to the cyclohexane (and the 2 and 4 carbon specifically- both on the cyclohexane ring). Sort of confused, I'm not reading the synthesis though.

I'm assuming by "that's not right" beenhead means my address isn't right, because I'm 99% sure that it isn't. The naming of the chem is right, because I trust this thing (no one's ever mentioned any of them being wrong before!)
 

Sturnam

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well, the first sentence of the article pretty much says that for the most part any modification of the cyclohexane ring will reduce potency 10-80 fold. so with few exceptions it sounds like it would be much better to focus on the piperidine ring.

not to mention the fact that this would still be illegal, so would it still really be worth making?
 

Ham-milton

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no it doesn't. It says that if you make the ring larger or smaller it really kills the potency.

It's odd that a hydroxy kills potency but a carbonyl doesn't (or much at least?), that much be a solubility or metabolism thing, not binding?
 

immaturepoop

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Ham-milton said:
no it doesn't. It says that if you make the ring larger or smaller it really kills the potency.

It's odd that a hydroxy kills potency but a carbonyl doesn't (or much at least?), that much be a solubility or metabolism thing, not binding?
Well I'm not one for pharmacology, but don't forget that a -OH group is more polar than a carbonyl group...
 

rangrz

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Canada eh, we get milk in bags.
Sturnam said:
not to mention the fact that this would still be illegal, so would it still really be worth making?
Oh really... The entire world is bound to the USA's analog act now?

oh wait... not every country has such an act. So this could be worthwhile in said countries.
 

hugo24

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Yes,4-Methoxiphenyl.The modifications are usually made via the Grignard reagent,being it 3-hydroxi to give more mu activity etc.

I'm not that sure if the Methoxi increases metabolism (polarity notwithstanding),it might well just protect that para position to some extent.
 

ralf2

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<pyridinyl_30> said:
That structure isn't right. The 4-methoxy goes on the phenyl ring, not the cyclohexane one.
That's what I said...

Ham-milton said:
Yes, it's the 4-carbon of the precursor- but not of the final product; the 4-carbon is on the cyclohexane in the final chem- so they are indeed talking about mods on the cyclohexane.

I'm not sure what you mean. The article is talking about mods to the cyclohexane (and the 2 and 4 carbon specifically- both on the cyclohexane ring). Sort of confused, I'm not reading the synthesis though.
This is the reaction. It is quite impossible for the methoxy group to end up on the cyclohexane ring.


(edit: larger version of picture)
 
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Ham-milton

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ralf2 said:
This is the reaction. It is quite impossible for the methoxy group to end up on the cyclohexane ring.

That's all good and well, but that reaction doesn't produce 4-methoxy-PCP.

The 4-carbon on PCP, according IUPAC naming conventions, is on the cyclohexane ring.
 

Ham-milton

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Yeah, you're right.

I never got to the page when the link didn't work, thanks for a correct link. That is indeed all that matters.

should I quote myself and start flaming or do you want to? :)

How he came to the name, I dunno, it's not correct (unless there's some other naming convention I'm unaware of). I love the last line though, "do you really want to be fighting a fire with fumes of a powerful psychoactive in the air" (or something to that affect)
 
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