Bufotenine esters.
R A Glennon, P K Gessner, D D Godse, B J Kline
Journal of medicinal chemistry November 1, 1979 Peer reviewed DOI: 10.1021/jm00197a025 via PubMed
Summary
Bufotenine, typically considered inactive in humans and animals, may gain new therapeutic potential through its esters. In a study involving isolated rat stomach preparations, acetyl, propionyl, butyryl, isobutyryl, and pivalyl esters of bufotenine displayed a notable affinity for serotonin receptors. This suggests that these modified compounds could potentially bypass the blood-brain barrier more effectively than bufotenine itself. Additionally, tests indicated minimal hydrolysis of the esters during the affinity assays, hinting at their stability and promise for further pharmacological evaluation.
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.