Bufotenine esters.

Bufotenine, a psychoactive compound, has weak behavioral effects in humans and animals, likely because it cannot easily cross the blood-brain barrier. Researchers synthesized several ester derivatives of bufotenine to evaluate them pharmacologically. Unexpectedly, all the esters showed strong affinity for serotonin receptors in isolated rat stomach tissue. Chromatographic analysis indicated that the esters were not extensively broken down into bufotenine during the assay, suggesting the esters themselves may be active at these receptors.

Study at a glance

Abstract

Bufotenine (5-hydroxy-N,N-dimethyltryptamine) has been reported to be behaviorally inactive or only very weakly active in man and animals; this may be a consequence of its low partition coefficient and resultant inability to penetrate the blood--brain barrier. The acetyl, propionyl, butyryl, isobutyryl, and pivalyl esters of bufotenine were prepared for future pharmacological evaluation. Unexpectedly, it was found that these esters all possess a relatively high affinity for the serotonin receptors of the isolated rat stomach fundus preparation. A semiquantitative chromatographic measurement of ester hydrolysis suggests that extensive hydrolysis of the esters to bufotenine does not occur under the conditions of the affinity assay.