Multiple tritium labelling of (+)‐7‐chloro‐8‐hydroxy‐1‐phenyl‐3‐methyl‐2,3,4,5‐tetrahydro‐1hZ‐3‐benzazepine (sch23390)

Steven D. Wyrick, Darryl L. McDougald, Richard Mailman

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

We previously reported the synthesis of the antidopaminergic‐antipsychotic agent SCH23390 labelled with tritium In the 9 position of the benzazepine ring system at a specific activity of 5.6 Ci/mmole as the racemic mixture. Here, we report the preparation of the higher specific activity (+)‐Isomer of SCH23390 labelled with tritium In both aromatic rings as well as the N‐methyl group. Multiple labelling was achieved by reductive debromination with carrier‐free tritium gas of a dibrominated N‐normethyl derivative over 5% Pd/C and subsequent N‐methylatlon with high specific activity methyl Iodide. The specific activity obtained for the Nor‐SCH23390 was 8.8 Ci/mmole and 93.8 Ci/mmole for the SCH23390.

Original languageEnglish (US)
Pages (from-to)685-692
Number of pages8
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume23
Issue number7
DOIs
StatePublished - Jan 1 1986

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Tritium
Labeling
Benzazepines
Isomers
Gases
Derivatives
SCH 23390

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Radiology Nuclear Medicine and imaging
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

Cite this

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abstract = "We previously reported the synthesis of the antidopaminergic‐antipsychotic agent SCH23390 labelled with tritium In the 9 position of the benzazepine ring system at a specific activity of 5.6 Ci/mmole as the racemic mixture. Here, we report the preparation of the higher specific activity (+)‐Isomer of SCH23390 labelled with tritium In both aromatic rings as well as the N‐methyl group. Multiple labelling was achieved by reductive debromination with carrier‐free tritium gas of a dibrominated N‐normethyl derivative over 5{\%} Pd/C and subsequent N‐methylatlon with high specific activity methyl Iodide. The specific activity obtained for the Nor‐SCH23390 was 8.8 Ci/mmole and 93.8 Ci/mmole for the SCH23390.",
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T1 - Multiple tritium labelling of (+)‐7‐chloro‐8‐hydroxy‐1‐phenyl‐3‐methyl‐2,3,4,5‐tetrahydro‐1hZ‐3‐benzazepine (sch23390)

AU - Wyrick, Steven D.

AU - McDougald, Darryl L.

AU - Mailman, Richard

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N2 - We previously reported the synthesis of the antidopaminergic‐antipsychotic agent SCH23390 labelled with tritium In the 9 position of the benzazepine ring system at a specific activity of 5.6 Ci/mmole as the racemic mixture. Here, we report the preparation of the higher specific activity (+)‐Isomer of SCH23390 labelled with tritium In both aromatic rings as well as the N‐methyl group. Multiple labelling was achieved by reductive debromination with carrier‐free tritium gas of a dibrominated N‐normethyl derivative over 5% Pd/C and subsequent N‐methylatlon with high specific activity methyl Iodide. The specific activity obtained for the Nor‐SCH23390 was 8.8 Ci/mmole and 93.8 Ci/mmole for the SCH23390.

AB - We previously reported the synthesis of the antidopaminergic‐antipsychotic agent SCH23390 labelled with tritium In the 9 position of the benzazepine ring system at a specific activity of 5.6 Ci/mmole as the racemic mixture. Here, we report the preparation of the higher specific activity (+)‐Isomer of SCH23390 labelled with tritium In both aromatic rings as well as the N‐methyl group. Multiple labelling was achieved by reductive debromination with carrier‐free tritium gas of a dibrominated N‐normethyl derivative over 5% Pd/C and subsequent N‐methylatlon with high specific activity methyl Iodide. The specific activity obtained for the Nor‐SCH23390 was 8.8 Ci/mmole and 93.8 Ci/mmole for the SCH23390.

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