Synthesis of potent sigma-1 receptor ligands via fragmentation of dextromethorphan

Mark P Arrington; Claire Brown; C Eric Schwartz

doi:10.1016/j.bmcl.2003.12.105

Synthesis of potent sigma-1 receptor ligands via fragmentation of dextromethorphan

Bioorg Med Chem Lett. 2004 Apr 5;14(7):1807-9. doi: 10.1016/j.bmcl.2003.12.105.

Authors

Mark P Arrington¹, Claire Brown, C Eric Schwartz

Affiliation

¹ UCB Research, Inc, 840Memorial Drive, Cambridge, MA 02139, USA.

PMID: 15026077
DOI: 10.1016/j.bmcl.2003.12.105

Abstract

Treatment of dextromethorphan 1 with various alkylating agents followed by base treatment led to Hoffman-type elimination reactions to produce a series of tricyclic derivatives, 6. These derivatives were characterized in vitro as sigma-1 receptor ligands.

MeSH terms

Dextromethorphan / chemical synthesis*
Dextromethorphan / metabolism*
Ligands
Protein Binding / physiology
Receptors, sigma / metabolism*
Sigma-1 Receptor

Substances

Ligands
Receptors, sigma
Dextromethorphan