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Report | Regular issue | Vol 23, No. 1, 1985, pp.99-106
Published online, 1st January, 1970
DOI: 10.3987/R-1985-01-0099
Probes for Narcotic Receptor Mediated Phonomena 11. Synthesis of 17-Methyl and 17-Cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphinans (Foxy and Cyclofoxy) as Models of Opioid Ligands Suitable for Position Emission Transaxial Tomography

Terrence R. Burke, Jr., Kenner C. Rice,* and Candace B. Pert

*Laboratoryof Chemistry, Medical Chemistry Section, National Arthritis Institute, National Institute of Health, Behesda, Maryland 20892, U.S.A.


Fluorinated derivatives 3,14-dihydroxy-4,5α-epoxy-6β-fluoro-17-methylmorphinan (“fluorooxymorphone”; FOXY, 10) and 17-cyclopropylmethyl-3,14-dihydroxy-4,5α-epoxy-6β-fluoromorphinan (CYCLOFOXY, 18) were prepared based upon the structures of the potent opioid agonist oxymorphone 4 and the antagonist naltrexone 11 respectively. Fluorine was introduced in the final stages of synthesis by a facile nucleophilic displacement with fluoride ion of the 6α-triflate functions in 8 and 16. The synthetic procedures are suitable for the production of the corresponding positron emitting 18F-labeled analogs 18F-FOXY and 18F-CYCLOFOXY, which may be useful for in vivo studies of the opioid receptor system using positron emission trans-axial tomography. In addition, the tritiation of FOXY (10) to high specific activity is described.