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Arecoline derivatives.

P

Phanerothyme

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I'm generally interested in hearing more about cocaine analogs derived from arecoline. The first image is cocaine, and the second the well known clark compound. I am unaware if the third molecule has ever been created, but it is essentially the o-benzoyl ester of p-hydroxy arecoline; which has quite a resemblance with cocaine. Without getting into synth discussion to much, what possible effect would creating the second (or third) compound without any 4-position substitution, or with different halides or an amino have on its pharmacology. The chlorophenylMg Br reagent seems fairly obscure. If one did have 4-hydroxy arecoline, esterification with various substituted benzoic acids would allow for relatively simple experimentation.
One thing that concerns me with the clark-type compounds (phenylpiperidines) as being potential recreational substances is the MPTP resemblance. Although I don't think one could easily create such a compound by accident (not in the same way mppp>mptp), the possible risk is quite scary, leading me to think esters are more likely the way to go. Though I believe they would be local anesthetics like cocaine, and therefore cardiotoxic?
Also, anyone think substituting the 2nd molecule at the 4 position on the piperidine ala meperidine or mppp might yield a compound with significant action at DAT and opioid receptors?
Sorry for the scattered thoughts and such, I've been looking at these different possibilities a lot lately and wanted to post to see if anyone else has done research into similar things. Also, seeing Mobius from ADH posting here too played a part, because he has provided the most info (non-science literature type) I've been able to find on the arecoline derivatives. Anyways, this is all for academic interest as I wouldn't feel qualified or safe in trying any of these things, not to mention legal aspects. Any info appreciated.
 
There's a huge thread called stimulants of the future. There's also a search engine. Most of the ideas you mention here have been discussed on the ADD. If you have access to American Chemical Society publications, most of the SAR data on these and every other modification you could think of has been published.
By the way, the stereochemistry of the methyl ester on your cocaine drawing is wrong.
Welcome to bluelight.
 
I do a lot more lurking than posting, as I find ADD really interesting, but all of you guys are way beyond me. I've been through the stimulants of the future thread, all good info. I guess I should of have said info not already on bluelight (or alt.drugs for that matter), but searching again I did come across smyth's unfavorable opinion of p-fluorophenyl-arecoline HBr, which is interesting, and I would like to hear more about it. I do have access to ACS and typical univeristy database stuff, and I've just recently been getting into using that sort of stuff (searching structures etc). I will being trying that soon, but I am also interested in anecdotal experiences. I saw some related info on the hive once, but haven't been able to find it again on any of the archives I know about. Was/is there much discussions of these derivatives on the hive or related boards (not registered at syntkl or wd.ws, hive was before my time in these matters, is there a complete archive anywhere?)
(Got the cocaine structure from wikipedia btw, guess you can't expect too much).
Anyways, thanks for the welcome.
 
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That third structure is quite like some piperidine-based cocaine analogs i've been looking at recently - different being that they have a ester linkage between the benzene ring and the piperidine ring - that'll reduce the potency heaps, but could be a lot easier to synthesize.
 
MattPsy said:
That third structure is quite like some piperidine-based cocaine analogs i've been looking at recently - different being that they have a ester linkage between the benzene ring and the piperidine ring - that'll reduce the potency heaps, but could be a lot easier to synthesize.
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And a lot less likely to produce a hideously neurotoxic compound like MPTP, which I think should be priority no 1 when fiddling with these compounds. I watched my gran die with Parkinson's and it's one of those unbelievably cruel diseases, like Huntindon's chorea & Altzheimer's /Creutzfeld-Jacob disease
 
It's currently part of designer supplements new dietary supplement called Adrenalean.

I have tried this formula as well as straight Arecoline and found the effects in very low doses 1-5 mg as a mild stimulant.
 
What is currently a part of Adrenalean (which from a quick google search seems to be name of several differnt products)?
 
Arecoline in betel or as plain stimulates but it lacks almost all other effects ("benefits") of usual stimulants. I mean it doesn't feel interesting at all, although I'm not the biggest fan of stimulants (anonymously claimed as one though) in general.

Arecoline could form interesting compounds when attached to tropane ring system (or whatever it is called) and when some cocaine like phenyltropane is thus formed.

Well, although plain arecoline lacks the stimulant buzz in me, I have been without any tobacco while chewed betel; and that in itself is very much. Other things which helped me to quit tobacco momentarily are those cathinone derivatives...
 
^ Due to dopamine (via nicotinic acetylcholine receptors for arecoline) activity. That's the little bugger that makes them hard to quit (bupropion/Zybasn, which is used to help stop smoking is a dopamine reuptake inhibitor).

BTW, betel nut is extremely bitter tasting and causes your mouth to overflow with saliva, so don't think you can use it in social situations to replace nicotine!
 
BTW, betel nut is extremely bitter tasting and causes your mouth to overflow with saliva, so don't think you can use it in social situations to replace nicotine!
Click to expand...

^ Yes betel is bitter, and in addition to watering mouth, betel "paints" ones saliva completely red! Spitting red saliva all over the places would be regarded as vulgar and arrogant behavior in the best, if tolerated at all. But it kills the craving to smoke tobacco.

Well, on the other hand, most people hate passionately smoking. Would red spit beat tobacco smoke in public places? =D
 
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