Synthesis and monoamine transporter affinity of 3α-arylmethoxy-3β-arylnortropanes

Harneet Kaur, Sari Izenwasser, Abha Verma, Dean Wade, Amy Housman, Edwin D. Stevens, David L. Mobley, Mark L. Trudell

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


A series of 3-arylnortrop-2-enes and 3α-arylmethoxy-3β-arylnortropanes were synthesized and evaluated for binding affinity at monoamine transporters. The 3-(3,4-dichlorophenyl)nortrop-2-ene (6e) exhibited high affinity for the SERT (Ki = 0.3 nM). The 3α-arylmethoxy-3β-arylnortropanes were generally SERT selective with the 3α-(3.4-dichlorophenylmethoxy)-3βphenylnortrop-2-ene (7c) possessing subnanomolar potency (Ki = 0.061 nM). However, 3α-(3,4-dichlorophenylmethoxy)-3β-phenylnortrop-2-ene (7b) exhibited high affinity at all three transporters [(DAT Ki = 22 nM), (SERT Ki = 6 nM) and (NET Ki = 101 nM)].

Original languageEnglish (US)
Pages (from-to)6865-6868
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Issue number24
StatePublished - Dec 15 2009


  • Dopamine
  • Monoamine transporters
  • Neurotransmitters
  • Norepinephrine
  • Serotonin
  • Tropanes

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry


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