tropine (Stranger)
06-02-03 07:00
No 437131
      Cocaine analogue synth from Arecoline - Correct?  Bookmark   

the wonderful yet vague synth on Rhodium's page has what looks to be a an chemical error on it.  Since we are attmepting the conjugate addition of an alkyl group (our chloro-phenyl guy) we would want to use a lithium diorganocopper reagent wouldn't we?  Using the straight up grignard would lead to direct carbonyl addition on our ester producing something funky, don't you agree Rhodium?

Edit: The link for the procedure is ../rhodium/chemistry /cocaine.analog.arecoline.html
 
 
 
 
    Megatherium
(Hive Bee)
06-02-03 15:12
No 437222
      Temperature control  Bookmark   

The reaction is carried out at - 10 C.  Low temperatures  favour conjugate addition.

Besides, the procedure is referenced from the JMC.  I don't think they would publish junk procedures tongue.
 
 
 
 
    hms_beagle
(Stranger)
07-01-03 07:02
No 443671
      It sounded good at the time  Bookmark   

The conjugate addition will work as described. Not to say that there might not be a better way to do the reaction though!

I'm less exited about this project than I used to be. From looking at the structural requirements for cocaine analogs, it seems that most of structure must be intact for high activity. I don't believe that the arecoline analog will be similar to cocaine in effects. No way to tell for sure without assaying it though. I still haven't seen a followup article from the originl authors.
 
 
 
 
    tropine
(Stranger)
07-01-03 07:29
No 443676
      WHy wouldn't structure be intact?  Bookmark   

I must agree that it looks too good to be true, and it would be great if someone else would try it and tell us the results, but why the doubt in the author's claims?  They do list it's "Hilman coefficient" , where it appears a lower number means better dopamine re-uptake inhibition, why do you doubt their data?  True it might not be a local anesthetic, but the euphoria would be I think indistinguishable from coke.
 
 
 
 
    superman
(Hive Bee)
07-08-03 09:33
No 445512
      mmmm...  Bookmark   

can anyone speculate as to whether or not i am wasting my time by adding this synth to my "to do when i can afford to" list?   would be nice to have a cheap replacement by halloween :)