The labelling of a novel tropane derivative [11C]NS 2214 (BMS-204756) - An inhibitor of the dopamine transporter

A. D. Gee, P. Moldt, A. Gjedde

Research output: Contribution to journalArticle

Abstract

The 11C-labelling of a novel tropane derivative (+)-(E)-(1R,2R,3S)-3-(3,4-dichlorophenyl)-8-[11C]methyl-8 -azabicyclo[3.2.1]octane-2-O-methyl-aldoxime (NS 2214 or BMS-204756), an inhibitor of the dopamine transporter (IC50 3 nM) is reported. (+)-(E)-(1R,2R,3S)-3-(3,4-dichlorophenyl)-8-azabicyclo[3.2.1]octane-2-O-methyl -aldoxime (NS 2262, either as the disulphate salt with added base or as the free amine) was alkylated with [11C]methyl iodide. The crude product was purified by HPLC using either a reverse phase or cyanopropyl stationary phase. Best results were obtained using the free amine as the labelling precursor and the cyanopropyl stationary phase for the HPLC purification. This resulted in the synthesis of radiochemically pure [11C]NS 2214 with a decay corrected radiochemical yield of 24-30%, specific activity > 50 GBq/μmol (>1.4 Ci/μmol), and a total synthesis time of less than 30 min (counted from EOB).

Original languageEnglish (US)
Pages (from-to)959-972
Number of pages14
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume39
Issue number12
DOIs
StatePublished - Dec 1997
Externally publishedYes

Fingerprint

Tropanes
Dopamine Plasma Membrane Transport Proteins
Labeling
Amines
High Pressure Liquid Chromatography
Derivatives
Inhibitory Concentration 50
Purification
Salts
brasofensine
acetaldehyde oxime
8-azabicyclo(3.2.1)octane
methyl iodide

Keywords

  • C
  • BMS-20457
  • Dopamine transporter
  • NS 2214
  • PET

ASJC Scopus subject areas

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

Cite this

The labelling of a novel tropane derivative [11C]NS 2214 (BMS-204756) - An inhibitor of the dopamine transporter. / Gee, A. D.; Moldt, P.; Gjedde, A.

In: Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 39, No. 12, 12.1997, p. 959-972.

Research output: Contribution to journalArticle

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