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- W2043832066 abstract "The authors of the present paper reported the synthesis of [11C]-ohmefentanyl in a symposium abstract in 1991(1). We here describe the results of synthesis and analysis in detail. Ohmefentanyl 1 is a novel, highly potent and selective agonist for opiate μ-receptors. In order to visualize the μ-receptor by Positron Emission Tomography (PET), this compound was labelled with carbon-11. The unlabelled cis-A-ohmefentanyl was prepared in a nine-step synthesis and two-step fractional crystallization, and the OH-precursor 11 for [11C]-ohmefentanyl labelling was obtained by hydrolysis of the 4-N-propionyl group of cis-A-ohmefentanyl in 6 N hydrochloric acid. The [11C]-propionyl chloride was prepared by carbonation of ethylmagnesium bromide with cyclotron-produced [11C]-carbon dioxide followed by direct treatment of the intermediate complex with phthaloyl dichloride and 2,6-di-t-butylpyridine. Reaction of the OH-precursor 11 with [11C]-propionyl chloride yields [11C]-ohmefentanyl separated by HPLC, with a high specific activity of 11.1 – 14.8 GBq μmol−1 (300−400 mCi μmol−1), 49 minutes after the end of bombardment. The keto-precursor 12, prepared by hydrolysis of the 4-N-propionyl group of cis-10 in 8 N hydrochloric acid, was also used for [11C]-ohmefentanyl labelling. Reaction of the [11C]-propionyl chloride with keto-precursor 12, followed by addition of sodium borohydride, yields [11C]-ohmefentanyl. The [11C]-labelled ohmefentanyl obtained using the OH-precursor 11 is a cis-A form, while that obtained using the keto-precursor is a mixture of cis-A and cis-B forms." @default.
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- W2043832066 date "1992-11-01" @default.
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- W2043832066 title "Synthesis of [11C]-ohmefentanyl, a novel, highly potent and selective agonist for opiate μ-receptors" @default.
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- W2043832066 doi "https://doi.org/10.1002/jlcr.2580311103" @default.
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