Bufotenine esters

J Med Chem. 1979 Nov;22(11):1414-6. doi: 10.1021/jm00197a025.


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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Bufotenin / analogs & derivatives*
  • Bufotenin / chemical synthesis
  • Bufotenin / metabolism
  • Bufotenin / pharmacology
  • Esters
  • Female
  • Hydrolysis
  • In Vitro Techniques
  • Male
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Rats
  • Receptors, Serotonin / metabolism
  • Serotonin / analogs & derivatives*
  • Structure-Activity Relationship


  • Esters
  • Receptors, Serotonin
  • Bufotenin
  • Serotonin