Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene

Scott P. Runyon; Scott P. Runyon; JE Savage; M Taroua; BL Roth; RA Glennon; RB Westkaemper

Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene

Runyon, SP., Savage, JE., Taroua, M., Roth, BL., Glennon, RA., & Westkaemper, RB. (2001). Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene. Bioorganic and Medicinal Chemistry Letters, 11(5), 655-658.

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Abstract

Comparison of the serotonin 5-HT2A receptor affinities of chain lengthened and N-alkylated analogues of the novel ligand 9-aminomethyl-9,10-dihydroanthracene (AMDA) and a structurally similar prototypical tricyclic amine imipramine suggests that the two agents bind to the receptor in different fashions. The demonstration that AMDA is highly selective for serotonin receptors (5-HT2A, K-i = 20 nM; 5-HT2c, K-i = 43 nM) versus the dopamine D-2 receptor (K-i >10,000 nM), as well as the serotonin and norepinephrine transporters (Ki >10,000 nM) further suggests that AMDA and the nonselective ligand imipramine interact with these target macromolecules in different ways. (C) 2001 Elsevier Science Ltd. All rights reserved.