O-Pivalylbufotenine, or bufotenine O-pivalate, also known as 5-pivaloxy-N,N-dimethyltryptamine (5-t-BuCO-DMT) or as O-pivalyl-N,N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O-pivalyl analogue of the naturally occurring but peripherally selective serotonergic tryptamine bufotenine (5-hydroxy-N,N-dimethyltrypamine or N,N-dimethylserotonin) and is thought to act as a centrally penetrant prodrug of bufotenine.
Use and effects
Interactions
Pharmacology O-Pivalylbufotenine is thought to be a prodrug of bufotenin and shows psychedelic-like effects in animal. However, it is less active than anticipated, perhaps due to its high lipophilicity and, by extension, high plasma protein binding and ester hydrolysis into bufotenin prior to crossing the blood–brain barrier. In addition to theoretically acting as a prodrug of bufotenine, which is a non-selective serotonin receptor agonist, O-pivalylbufotenine may also interact directly with certain serotonin receptors.
Chemistry
Analogues Analogues of O-pivalylbufotenine (5-t-BuCO-DMT) include bufotenin (5-HO-DMT), 5-MeO-DMT (mebufotenin), and 4-AcO-DMT (psilacetin), among others. In addition, besides O-pivalylbufotenine, other bufotenine O-acyl esters and putative or confirmed bufotenine prodrugs, such as O-acetylbufotenine among others, have been developed and studied.
History O-Pivalylbufotenine was first described in the scientific literature by 1979.
See also Substituted tryptamine O,O′-Diacetyldopamine O,O′-Dipivaloyldopamine α-Methyltryptophan Neurotransmitter prodrug Psilacetin
References
External links 5-(2,2-Dimethylpropanoyloxy)-DMT - Isomer Design