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
Public Deposited- Creator
- Pigott, Adam
- Frescas, Stewart
- McCorvy, John D
- Huang, Xi-Ping
- Roth, Bryan L
- Nichols, David E
- 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-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 – although (−)-4 and (−)-5 may be useful as tools to probe 5-HT2 receptor function – one would need to be mindful that their selectivity for 5-HT2A receptors is somewhat less than for DOI itself.
- Date of publication
- 2012
- Keyword
- DOI
- Identifier
- Publisher DOI: https://doi.org/10.3762/bjoc.8.194
- PMCID: PMC3511003
- Onescience id: a15ec1b856db3973bdcaee1e9fcff4297739931b
- PMID: 23209503
- Resource type
- Article
- Rights statement
- In Copyright
- Journal title
- Beilstein Journal of Organic Chemistry
- Journal volume
- 8
- Language
- English
- ISSN
- 2195-951X
- 1860-5397
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