The Vespiary

The Hive => Serious Chemistry => Topic started by: tropine on June 02, 2003, 07:00:00 AM

Title: Cocaine analogue synth from Arecoline - Correct?
Post by: tropine on June 02, 2003, 07:00:00 AM

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

https://www.thevespiary.org/rhodium/Rhodium/chemistry/cocaine.analog.arecoline.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/cocaine.analog.arecoline.html)

Title: Temperature control
Post by: Megatherium on June 02, 2003, 03:12:00 PM

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  :P .

Title: It sounded good at the time
Post by: hms_beagle on July 01, 2003, 07:02:00 AM

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.

Title: WHy wouldn't structure be intact?
Post by: tropine on July 01, 2003, 07:29:00 AM

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.

Title: mmmm...
Post by: superman on July 08, 2003, 09:33:00 AM

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 :)