tomjuan (Hive Bee)
11-26-01 09:49
No 240664
      2-carbomethoxy-fluorophenyl-tropane  Bookmark   

Does anyone have any information about (or references for) this compound? All I have found thus far is a claim on a website it is a cocaine analog that is 60 times more potent than cocaine (it gives "Clark et. al, 1973" as the reference for this), and one synthesis reference from a journal that I have never heard of: "Bergman J, Haaparanta M and Solin O, Synthesis of 2-carbomethoxy-3-(fluorophenyl)tropane ([18F]CFT or [18F]WIN 35428), J. Label. Comp. Radiopharm. 1995; 37: 46-48. [C,Prim]". I can't find either of the references, but I'm very curious. Any info would be greatly appreciated.
(Chief Bee)
11-26-01 09:55
No 240667
      Re: 2-carbomethoxy-fluorophenyl-tropane  Bookmark   

Either this syhthesis, but with di-(4-fluorophenyl)copperlithium as alkylation reagent and methanol in the last esterification step: Post 223726 (Rhodium: "Cocaine analog", Novel Discourse)

Or this one, using anhydroecgonine/4-fluorophenylmagnesium bromide instead of arecoline/4-chlorophenylmagnesium bromide as starting material: Post 108739 (dormouse: "Structurally simple cocaine analogs  -Beagle", Novel Discourse)
(Old P2P Cook)
11-26-01 10:01
No 240673
      Re: 2-carbomethoxy-fluorophenyl-tropane  Bookmark   

Once, about 20 years ago, I ran across an article in a Journal of Medicinal Chemistry (or somesuch journal) about cocaine analogs. At least one of the analogs was fluorinated and may even have been the one that you refer to. They had been tested for activity using rats. I would not want to be the first human test subject.
(Hive Bee)
11-26-01 10:18
No 240682
      Re: 2-carbomethoxy-fluorophenyl-tropane  Bookmark   

I would not want to be the first human test subject.

Of course not! Isn't that what ex-girlfriends are for? Seriously though, thanks for the info. SWIM is not planning to make anything for which no pharmacological data exists, so if he can't find any real references, he'll probably drop it. Also, it looks like it takes a lot of steps to effect the conversion - that's a lot of chances for SWIM to screw up, as he is prone to do with lengthy processes.

(Hive Bee)
11-27-01 07:01
No 241108
      Re: 2-carbomethoxy-fluorophenyl-tropane  Bookmark   

There is alot of biological data on this compound, and other halo substituted 2-carbomethoxy-phenyltropanes. I have more than a couple references, mostly from JMC. I'll get the ref's.