A strategy to replace the ethylamine side chain of 2,5-dimethoxy-4- iodoamphetamine (DOI, 1a), and 2,5-dimethoxy-4-bromoamphetamine (DOB, 1b) with a cyclopropylamine moiety was successful in leading to compounds with high affinity at the 5-HT 2 family of receptors; and the more potent stereoisomer of the cyclopropane analogues had the expected (-)-(1R,2S)- configuration. Screening for affinity at various serotonin receptor subtypes, however, revealed that the cyclopropane congeners also had increased affinity at several sites in addition to the 5-HT 2A and 5-HT 2B receptors. Therefore, at appropriate doses - although (-)-4 and (-)-5 may be useful as tools to probe 5-HT 2 receptor function - one would need to be mindful that their selectivity for 5-HT 2A receptors is somewhat less than for DOI itself. © 2012 Pigott et al; licensee Beilstein-Institut.
CITATION STYLE
Pigott, A., Frescas, S., McCorvy, J. D., Huang, X. P., Roth, B. L., & Nichols, D. E. (2012). Trans-2-(2,5-dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT 2 receptor family. Beilstein Journal of Organic Chemistry, 8, 1705–1709. https://doi.org/10.3762/bjoc.8.194
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