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  Benzofuran Bioisosteres of Hallucinogenic Tryptamines Left click: open entry/Right click: save entry
The benzofuran analogues of the hallucinogens 5-methoxy-N,N-dimethyltryptaminaen d 5-methoxy-cy-methyltryptamine
were synthesized and evaluated for affinity at the serotonin 5-HTz and 5-HT1r~e ceptors in rat brain
homogenate, labeled with [1~I]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoprop(a [1ne2 61]DOI)a nd [3H]-Shydroxy-
2-(N,N-di-n-propylamino)tetrali(n[ 3H]-8-OH-DPAT),r espectively. At the 5-HT2 receptor, the benzofurans had
slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines
and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTM receptor, but decreased
only about 20-30% from that of the indole isosteres. Thus, the 5-HTM receptor is less discriminating with respect
to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the
5-HTz receptor than for the 5-HTM receptor. It is suggested that benzofurans may be useful in the design of sertonin
receptor ligands.

J. Med. Chem. 1992,35, 2061-2064

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