Bufotenine esters.
Richard A Glennon, Peter K. Gessner, Damodar D. Godse, B J Kline
Journal of Medicinal Chemistry November 1, 1979 DOI: 10.1021/jm00197a025 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Laboratory study Peer reviewed |
|---|---|
| Population | Isolated rat stomach fundus |
| Interventions | acetyl propionyl butyryl isobutyryl and pivalyl esters of bufotenine |
| Citations | 17 |
| Key points | Ester derivatives of bufotenine unexpectedly show high affinity for serotonin receptors in rat stomach tissue, and this activity is not due to hydrolysis back to bufotenine. |
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.