Synthesis of a radiotracer for studying σ receptors in vivo using PET: (+)-N-[11C]-benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan)

J. L. Musachio, William B Mathews, H. T. Ravert, F. I. Carroll, Robert F Dannals

Research output: Contribution to journalArticle

Abstract

(+)-N-[11C]-Benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan), a potent and selective ligand for the σ receptor, was prepared by N-benzylation of (+)-cis-N-normetazocine with [α-11C]-benzyl iodide in ethanol using sodium hydrogen carbonate as the proton acceptor. The radiotracer was purified by semi-preparative reverse-phase HPLC. The average specific activity was 746 mCi/μmol calculated at end-of-synthesis (EOS). The average time of synthesis including formulation was 35 minutes.

Original languageEnglish (US)
Pages (from-to)49-57
Number of pages9
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume34
Issue number1
DOIs
StatePublished - 1994

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Sodium Bicarbonate
Iodides
Protons
Ethanol
High Pressure Liquid Chromatography
Ligands
normetazocine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Clinical Biochemistry
  • Molecular Medicine
  • Pharmacology

Cite this

@article{6396384686d1479aae11dbdb728280be,
title = "Synthesis of a radiotracer for studying σ receptors in vivo using PET: (+)-N-[11C]-benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan)",
abstract = "(+)-N-[11C]-Benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan), a potent and selective ligand for the σ receptor, was prepared by N-benzylation of (+)-cis-N-normetazocine with [α-11C]-benzyl iodide in ethanol using sodium hydrogen carbonate as the proton acceptor. The radiotracer was purified by semi-preparative reverse-phase HPLC. The average specific activity was 746 mCi/μmol calculated at end-of-synthesis (EOS). The average time of synthesis including formulation was 35 minutes.",
author = "Musachio, {J. L.} and Mathews, {William B} and Ravert, {H. T.} and Carroll, {F. I.} and Dannals, {Robert F}",
year = "1994",
doi = "10.1002/jlcr.2580340107",
language = "English (US)",
volume = "34",
pages = "49--57",
journal = "Journal of Labelled Compounds and Radiopharmaceuticals",
issn = "0362-4803",
publisher = "John Wiley and Sons Ltd",
number = "1",

}

TY - JOUR

T1 - Synthesis of a radiotracer for studying σ receptors in vivo using PET

T2 - (+)-N-[11C]-benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan)

AU - Musachio, J. L.

AU - Mathews, William B

AU - Ravert, H. T.

AU - Carroll, F. I.

AU - Dannals, Robert F

PY - 1994

Y1 - 1994

N2 - (+)-N-[11C]-Benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan), a potent and selective ligand for the σ receptor, was prepared by N-benzylation of (+)-cis-N-normetazocine with [α-11C]-benzyl iodide in ethanol using sodium hydrogen carbonate as the proton acceptor. The radiotracer was purified by semi-preparative reverse-phase HPLC. The average specific activity was 746 mCi/μmol calculated at end-of-synthesis (EOS). The average time of synthesis including formulation was 35 minutes.

AB - (+)-N-[11C]-Benzyl-N-normetazocine (1S,5S,9S-(+)-cis-2-[11C]-benzyl-2'-hydroxy-5,9-dimethyl-6,7-benzomo rphan), a potent and selective ligand for the σ receptor, was prepared by N-benzylation of (+)-cis-N-normetazocine with [α-11C]-benzyl iodide in ethanol using sodium hydrogen carbonate as the proton acceptor. The radiotracer was purified by semi-preparative reverse-phase HPLC. The average specific activity was 746 mCi/μmol calculated at end-of-synthesis (EOS). The average time of synthesis including formulation was 35 minutes.

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