Linked Life Data

7996545

Source:http://linkedlifedata.com/resource/pubmed/id/7996545

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
25
pubmed:dateCreated
1995-1-13
pubmed:abstractText
A method was found to synthesize 1-(2,5-dimethoxy-4-(trifluoromethyl) phenyl)-2-aminopropane, 5, and its des-alpha-methyl congener 2-(2,5-dimethoxy-4-(trifluoromethyl)phenyl)aminoethane, 6, the trifluoromethyl analogs of substituted hallucinogenic phenethylamine derivatives such as 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (3, DOI) that are potent 5-HT2A/2C agonists. In our hands, 5 and 6 have proven to have affinity for [3H]ketanserin or [125I]-3-labeled 5-HT2A/2C sites in rat cortex comparable to or higher than the analogous bromo or iodo analogs. Similarly, 5 and 6 had potency comparable to or slightly greater than that of their bromo or iodo congeners in the two-lever drug discrimination assay in rats trained to discriminate saline from LSD tartrate. The agonist properties of 5 and 6 were evaluated by measuring the accumulation of [3H]inositol monophosphate in cultured cells selectively expressing either 5-HT2A or 5-HT2C receptors. In comparison to serotonin (5-HT), compounds 3 (DOI), 5, and 6 were equally efficacious and full agonists at the 5-HT2C receptor. Similarly, 3 and 5 produced equivalent responses at the 5-HT2A receptor as compared to 5-HT. In contrast, 6, the alpha-desmethyl analog of 5, was only half as potent at stimulating inositol monophosphate accumulation at the 5-HT2A receptor. In conclusion, the title compound 5 and its alpha-desmethyl congener 6 appear to be the most potent of the so-called hallucinogenic amphetamine 5-HT agonists reported to date. Further, the reduced efficacy of 6 at the 5-HT2A receptor may offer at least a partial explanation for the observed higher in vivo potencies of alpha-methyl-substituted compounds in this series.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Dec
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:day
9
pubmed:volume
37
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4346-51
pubmed:dateRevised
2010-11-18
pubmed:meshHeading
pubmed-meshheading:7996545-3T3 Cells, pubmed-meshheading:7996545-8-Hydroxy-2-(di-n-propylamino)tetralin, pubmed-meshheading:7996545-Animals, pubmed-meshheading:7996545-Binding, Competitive, pubmed-meshheading:7996545-Cell Line, pubmed-meshheading:7996545-Discrimination (Psychology), pubmed-meshheading:7996545-Frontal Lobe, pubmed-meshheading:7996545-Hippocampus, pubmed-meshheading:7996545-Iodine Radioisotopes, pubmed-meshheading:7996545-Ketanserin, pubmed-meshheading:7996545-Male, pubmed-meshheading:7996545-Mice, pubmed-meshheading:7996545-Phenethylamines, pubmed-meshheading:7996545-Phosphatidylinositols, pubmed-meshheading:7996545-Rats, pubmed-meshheading:7996545-Rats, Sprague-Dawley, pubmed-meshheading:7996545-Receptors, Serotonin, pubmed-meshheading:7996545-Serotonin, pubmed-meshheading:7996545-Serotonin Receptor Agonists, pubmed-meshheading:7996545-Tritium
pubmed:year
1994
pubmed:articleTitle
1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist.
pubmed:affiliation
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907-1333.
pubmed:publicationType
Journal Article, Comparative Study, Research Support, U.S. Gov't, P.H.S.