title: 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.
abstract: 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.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University, West Lafayette, IN 47907, USA.
authors.forename: Adam
authors.initials: A
authors.lastname: Pigott
authors.forename: Stewart
authors.initials: S
authors.lastname: Frescas
authors.forename: John D
authors.initials: JD
authors.lastname: McCorvy
authors.forename: Xi-Ping
authors.initials: XP
authors.lastname: Huang
authors.forename: Bryan L
authors.initials: BL
authors.lastname: Roth
authors.forename: David E
authors.initials: DE
authors.lastname: Nichols