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Piperidine cocaine analog

haribo1

haribo1

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2.5x more potent as potent as cocaine as a dopamine reuptake inhibitor.
Highly potent serotonin reuptake inhibitor.

I saw it on your friend and mine, Wikipedia.

Now, one thing I'm interested in is the replacement of the methyl ester with an isopropyl ester since this seems to legnthen action...
 
What about leaving out the ester group all together? Leaving out the ester group makes it more resistant to metabolition, as esters are relatively weakly bonded. Though the bulkier isopropyl group may lengthen it's action, leaving out the ester group alltogether will lengthen it even a lot more.
 
Consistent with results reported in the literature for the tropane analogues, removal of the methyl group from the nitrogen atom of 9 leads to a further enhancement in 5-HTT activity.

NOTE: The 2.5x figure is misrepresented i believe for the aforementioned compound as it refers to another compound in the series and this one is noted it appears to be more potent
 
could you reduce the naphthalene down to a benzene and retain activity??

it's look a lot more cocaine-ish, but even still ,this is hardly an analogue!
 
The napthalene appears to be needed. The isomer shown is the only active one. You do need something like an ester there. A Reversed ester or maybe a ketone would do, but I'm just guessing.
 
these compounds are the clarke phenyl piperidines. and were originally described in the phenyltropane paper of 1973
http://www.erowid.org/archive/rhodium/djvu/clarke.djvu

A quick summary is that some of them have high activity as DAT inhibitors as well as SERT. SERT activity is retained even when the piperidine ring is opened! however they lack the locomotor stimulant activity of cocaine in rats and mice. some of the series have been investigated for cocaine substitution therapy a la methadone for opiates.

the various possible stereo isomers have been investigated, the 2 beta 3 beta isomers are the most effective dat inhibitors, this is the same orientation as in natural cocaine.

they have been discussed here before, ADD is like groundhog day
 
I love the sweet, fruity N,beta-methyl esters found in acacia, methylphenidate, and cocaine.

It's too bad they don't last longer metabolically. This compound makes me want to learn more about naphtha-2-yl amphetamines.

Anybody know anything about them?
 
Oh no, my bad, not acacia but rather areca which is usually chewed with betel leaves. The active ingredient is arecoline, or N-methyl-3-CO2CH3-piperid-3-ene.

I think they call it paan. I stumbled across this dip/snuff by accident. One night I went to the convenience store and happened to mention to the Indian clerk that I was trying to quit smoking cigaretttes, and he said, "Here, try this."

The snuff was quite good, both in taste and effect, but I pissed him off when I went back and asked how I could get some more. He didn't want to sell me any.
 
<pyridinyl_30> said:
Oh no, my bad, not acacia but rather areca which is usually chewed with betel leaves. The active ingredient is arecoline, or N-methyl-3-CO2CH3-piperid-3-ene.

I think they call it paan. I stumbled across this dip/snuff by accident. One night I went to the convenience store and happened to mention to the Indian clerk that I was trying to quit smoking cigaretttes, and he said, "Here, try this."

The snuff was quite good, both in taste and effect, but I pissed him off when I went back and asked how I could get some more. He didn't want to sell me any.
Click to expand...

I thought the areca was the bettle (nut). I'm a big fan myself. I chewed paan at least twice a day most days when I was in India. Now I've just got arecoline crystal which I dilute in water and consume. 20mg has me buzzing along at work.
 
I would not be surprised if this compound has some affinity to some 5-HT receptors.1-Naphtylpiperazine is a 5-HT2 antagonist and a 5-HT1 agonist,altough this here is a 2-naphtylpiperidine,but Quipazine is a 2-chinolyl variant,maybe the carbonyl of the ester here can mimick the hetero nitrogen of Quipazine?Anyone tried it?
 
activity is retained even when the piperidine ring is opened!
Click to expand...
2 vecktor
Do you have more information or refs about this compounds?
Edit
I find some - McElvain in 1924 synth open-chain piperidine analog. (JACS 46,1721). He say "It has about one-third the toxicity of cocaine, but produces practically no anesthesia when applied
to the rabbit's cornea"
"Toxicity of cocaine" maybe he mean "activity of cocaine", anyway this compound hard to synth than piperidine ring.
 
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