%0 Journal Article
%T trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT2 receptor family
%A Adam Pigott
%A Stewart Frescas
%A John D. McCorvy
%A Xi-Ping Huang
%J Beilstein Journal of Organic Chemistry
%D 2012
%I 
%R 10.3762/bjoc.8.194
%X 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-HT2 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-HT2A and 5-HT2B receptors. Therefore, at appropriate doses ¨C although ( )-4 and ( )-5 may be useful as tools to probe 5-HT2 receptor function ¨C one would need to be mindful that their selectivity for 5-HT2A receptors is somewhat less than for DOI itself.
%K cyclopropanation
%K diazomethane
%K hallucinogen
%K 5-HT2A agonist
%K receptor probe
%K trans-2-phenylcyclopropylamines
%U http://dx.doi.org/10.3762/bjoc.8.194