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2-(1-phenylcyclopentyl)ethanamine

Hammilton

Hammilton

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Sep 2, 2008
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Surprisingly, despite being a fairly obvious chemical structure, i cannot find anything about this molecule. I might have the terminology wrong, but I'm looking into the arylcyclohexylamine derivatives with two carbons between the amine and the cyclohexane.

Or in this case, the cyclopentane. I'm interested in using pentoxyverine as a precursor for an opioid, so I'm trying to determine if the molecule I'm thinking of is indeed an opioid. I'm thinking N,N-diethyl or dimethyl. Based on this structure, aside from the desired and hoped for opioid effects, I'd suspect that it would be a stimulant as well.

This is the structure I'm interested in (or the cyclohexane derivative)

4uCUgyQ.png


Is there anything published on it, or any close analogues?



Alternatively, I think from pentoxyverine a Clofenciclan analogue would be easily made as well, and that looks like a good stimulant, imho.

I don't see any reason to think that cyclopentane would be less active than cyclohexane in the clofenciclan analogue. Actually, lacking the para-chloro would probably be better, imho.

Shouldn't be hard to go from this:
220px-Pentoxyverine_skeletal.svg.png


to the cyclopentane, deschloro analogue of this:
200px-Clofenciclan_Structural_Formulae.png
 
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That compound looks a bit like tramadol:

tramadol.jpg


Note the distance of three carbons between the aromatic ring and the amine nitrogen in both structures. In your molecule, only one of those carbons is part of the alicyclic ring, though...

Anyone know whether a tramadol analogue without the hydroxyl group would be active?
 
Yeah, that would be O-methyl-Faxeladol.

I really need information on the compound in question though. SAR seems to suggest that it'd be a stimulant and opioid.
 
200px-Phencyclidine_structure.svg.png


Looks a bit like this, with a missing ring and rings switched around. Bet you could get some analogs of your theoritical chemical that are dissociatives, stimulants, and opioids.
 
I have nothing of substance to add but ok I must ask why you care about such things? I mean, unless you want to patent some substrate/peptide etc. and make a lot of money.

Why not work on the drugs already discovered/tested? All my questions predicate on the goal of more safe drug usage. Yours, and don't get me wrong, you're probably pretty knowledgeable, consistently hinge on unknown chemicals, with potentially negative ramifications for the amateur chemist/high-searching kid with a lab.
 
Ho-Chi-Minh said:
I have nothing of substance to add but ok I must ask why you care about such things? I mean, unless you want to patent some substrate/peptide etc. and make a lot of money.

Why not work on the drugs already discovered/tested? All my questions predicate on the goal of more safe drug usage. Yours, and don't get me wrong, you're probably pretty knowledgeable, consistently hinge on unknown chemicals, with potentially negative ramifications for the amateur chemist/high-searching kid with a lab.
Click to expand...


Pffft. Imagine if someone said that to Dr. Shulgin. What is it with people who can't imagine motivations exist outside of one's own motivations?
 
Hammilton said:
Nothing huh
Click to expand...

The closest chemical I can Google in short notice is caramiphen. This kind of looks like your proposed chemical except there is an additional ketone group attached to that big long chain on the pentyl. It apparently is an anti-convulsant used to treat Parkinson's disease, and an anti-tussive.

No references to recreational opioid activity for that compound, there is some data on this is as an analgesic but I guess more like a novocaine than what you want. Though realistically adding a ketone group to that long chain could significantly change the effects, anything is possible. But still, there is an equal chance of disappointment here, I think.

Edit: I see you already found clofenciclan which is even closer, heh. That is a stimulant + anaesthetic, but there's not much else on it. Since caramiphen also has anaesthetic properties, perhaps this compound at least has this property. Not the same thing as opioid though. One other thing, caramiphen in the edisylate form at least is an NMDA antagonist of some sort, so perhaps there is something in *this* direction (dissociative) with this new compound.
 
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HoChiMin said:
I must ask why you care about such things?
Click to expand...

I'm guessing because they're intrinsically interesting. . .at least I think that they are.

ebola
 
Forgive me if I didn't say "maybe this compound could be less toxic than existing compounds, that's why we should look into it." There, I've said it. It's hard to worry about toxicity when potency and even activity are entirely unknown. But by your thinking we shouldn't bother looking into novel substances just because they're unknown yet. lol.

I'm not Shulgin. My interests lie mainly with computer modelling in predicting activity of potential new psychoactives. It was actually by comparing dozens of compounds to the pharmacophore model of DARI's I put together (though this effort was indeed are replication of a study done three years previous to my efforts, I wasn't simply copying them- I was unaware of their research until I had completed my own!) that I came across clofenciclan, or rather the deschloro analogue. I was looking for compounds that fit the pharmacophore and then googling the IUPAC to see if they already existed. That analogue wasn't found, but it was surely researched by those who made clofenciclan. It has yet to be sold as an RC, but the way things are going I would be somewhat shocked if it is not eventually.

The compound in question in this thread is a pretty basic compound designed to fit the morphine rule. For your benefit I'll restate it here:

1) Tertiary Amine
2) Two Carbon spacer connecting to
3) Quaternary Carbon adjacent to
4) Aromatic ring (usually phenyl, although thiophene seems to work well, see diethylthiambutene).

There are opioids which don't fit this rule, like tapentadol, but as far as whole classes go, they're relatively uncommon. The big exception, of course, is the whole fentanyl family.


Anyway, back to the interesting stuff.

I have found a closer compound, one I believe is probably active. It's called Dihydrojoubertiamine. I don't think Joubertiamine itself is likely to be a strong opioid, but i'd be surprised if Dihydrojoubertiamine wasn't at least as strong as pethidine. The benefit being that like pethidine, it's probably a weak DARI.

680235-2-(1-phenylcyclopentyl)ethanamine


Dihydrojoubertiamine is a direct precursor to mesembrine. You can see how one is obtained from the other. I'm wondering if perhaps some of mesembrine's reputed recreational effects may come from DHJA present in the mesembrine extracts. Perhaps mesembrine itself has some weak opioid affinity.

It kind of reminds me of some of the "what's the simplest morphine-rule-fulfilling compounds out there" suggestions from way back when.

Unfortunately, DHJA appears to be entirely untested, which is exciting itself, but with such a promising structure, it seems surprising that it was overlooked. Overlay with oxycodone is pretty good, but a 3-hydroxy would be favored over para, but I guess you take what you can get. At least it's not methylated, which would be even worse.
 
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Does the basis of this structure resemble arylcyclohexylamine structures at all? Or is the similarity merely in the 2D representation?
 
arylcyclopentylamines are considered to be inactive, so no
 
I'm not sure what sekio's point is, the structures are similar, in a way, but it's unlikely to be a strong dissociative.

And Bloodshed344, neither Dihydrojoubertiamine or the compound named in the OP are arylcyclohexylamines or cyclopentylamines. There is a two carbon spacer between the cycloalkyl group and the amine. They would be best called arylcycloalkylethanamines.

I'm not looking for active dissociatives with my research here. I'm simply looking at opioid and stimulant activity. I suspect these compounds will be Mu agonists and mixed NDRI's; maybe releasers, but I wouldn't put money on that.

I think my current goal will be to obtain dihydrojoubertiamine and give it a tasting, I have high hopes for it. I wonder if it'd be possible to replace that ketone with 2H without damaging the phenol OH. Would probably need to be protected. Still, I don't see any reason why that ketone would hinder opioid affinity. It's not exactly analogous to the ketone in oxycodone, but not too dissimilar either.
 
Right, but they're not either. they're arylcycloalkylethanamines. The difference is not moot.
 
does the change from arylcycloalkylamines to arylcycloalkylethanamines confer more of a stimulant activity?
Click to expand...

We don't know... all I was pointing out is that the analogues of e.g. PCP and ketamine with 5-membered rings are much less active as dissociatives than the 6-membered ones. That is all I was observing, not making claims that this particular compound is going to be a dissociative.

Dihydrojoubertamine reminds me a little of the pethidine SAR. But I can't find any listings for bioactivity of the joubertamine alkaloids.
 
sekio said:
We don't know... all I was pointing out is that the analogues of e.g. PCP and ketamine with 5-membered rings are much less active as dissociatives than the 6-membered ones. That is all I was observing, not making claims that this particular compound is going to be a dissociative.

Dihydrojoubertamine reminds me a little of the pethidine SAR. But I can't find any listings for bioactivity of the joubertamine alkaloids.
Click to expand...

Oh I wasn't pointing my question at you. I was asking hammilton because he was interested in finding DARI activity, and plus I was interested if the change from a regular amine to an ethanamine would confer more stimulant activity by being closer to phenethylamine structure.
 
I don't think so. For one, it's a tertiary amine. Two, the ring beta to the amine isn't aromatic, so it's not really closer to a phenethylamine. Actually, both arylcyclohexylamines and arylcycloalylethanmines are exactly one carbon away from containing the PEA skeleton.

I'm going to be brief because my tremors are getting the worst of me today and typing is getting tough (and it's only 3pm here!).

I'll switch computers and upload my overlay actually. that's a better use of time, I think.
 
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